What to Carry on a First Date: The Gentleman’s Arsenal

by Brett on May 19, 2010 · 181 comments

in Dating, Relationships & Family

The First Date with a woman is your chance to display your charming and chivalrous side. While most acts of chivalry (like opening a door for your date or helping her to her seat) require only your thoughtfulness, moments will arise when you’ll need a tool to assist in your kindness. Below I’ve included a short list of items I recommend a well-armed gentleman having on him during a first date (or any time for that matter) that will prepare him for any situation and leave his date impressed.


Before you head out on your date, slip a clean, pressed white hankie into your pocket. When your date tears up during the movie you’re seeing, she’ll appreciate the offer of a soft hankie. Hankies can come in handy in non-crying situations, too. If your date gets grease or food on her clothing, give her your hankie so she can clean herself up. Let her keep it when she’s done with it. First, it might have her snot in it. Second, when she does get around to washing it, your hankie will serve as a reminder of how awesome you are. She won’t be able to wait to go on a second date with you.


Nom nom nom. That garlic infused steak topped with garnished onions was delicious. But now your breath reeks to high heaven. Trust me. Your date doesn’t want to smell what you ate for dinner the rest of the night. Show some courtesy by popping a few mints as you step out of the restaurant.  You’ll only be increasing your chances for that first kiss. Your date will probably be looking for something to freshen up her breath during the date as well, so make sure you’re prepared when she asks if you have anything that will do the trick.

“Everything had its own little home, neat and tidy. The white linen handkerchief on the inside pocket. The little mints… A single key on a fob.” -Nancy Sinatra on the contents of Frank Sinatra’s pockets


It seems the whole world has gone plastic, but a gentleman should always have cash on him, particularly on a date. Why carry cash? Most parking places and some toll roads don’t accept credit and debit cards. When you pull up to the crusty old parking lot attendant, you don’t want to be scrounging around for change in your cup holder, or even worse, asking your date to pay. And you’ll want to take your date to a small, interesting restaurant instead of a generic chain place, and many mom and pop joints don’t take credit cards. Imagine your panic when the check arrives and all you have is a useless card. Also, even if the establishment does take plastic, you’ll need plenty of cash on hand to cover tips throughout the night. Sure, you can often take care of this with debit cards, but there’s something a bit more personal about greasing a palm with cold hard cash. Besides, most waiters I know prefer getting tipped in cash. Finally, stopping at a roadside stand for some ice cream is always a nice finale to a date, and once again, most don’t take cards. So stash some of that green stuff in your wallet.


When a woman has spent an hour or two getting dolled up for a date, she doesn’t want the effect ruined by stepping out into the rain. Stash an umbrella in your car, and you’ll always be prepared to keep her dry. If it’s raining during your date, keep your umbrella with you so you can always protect her from the elements. In those moments it’s not raining, an umbrella can double as a Bartitsu weapon to knock in a hooligan’s head.

A Sports Coat

The sports coat serves two purposes in a gentleman’s arsenal. First, jeans, a button down shirt and a sports coat is a can’t fail look to impress your date and help you look your best. Second, dressing in layers allows you to offer your jacket to a lady no matter what the weather or need for an overcoat. If it gets chilly at the museum or while strolling together at night, you’ll be prepared. The gesture of offering your jacket, in addition to simply being chivalrous, will score you innumerable points with your date; feeling cozy in your coat will make her feel closer to you. A sports coat also has handy pockets for your other tools; some even have special ticket pockets to stash the tickets for the show you’ll be seeing.

What other items should a man carry on a date? Share your ideas in the comments!

{ 181 comments… read them below or add one }

1 Lucas May 19, 2010 at 1:33 am

Condoms! And plenty of KY Jelly!

2 Michael May 19, 2010 at 2:06 am

I think a condom would fall under the “be prepared” banner, although it could be said that if you’re interested in her as a long-term girlfriend, you might want to keep it in your pants for at least one night. Leave her wanting more, as they say in showbiz.

Maybe Brett’s assuming a modern gentleman always carries a phone, but if not, I’ve found that even back in the days when mine was a black brick with a 3-line display it came in very handy for making last-minute changes in plans. Nowadays an iPhone can contain a virtual arsenal, from maps to recommendations to photos of Spot to make her heart melt.

3 Philip May 19, 2010 at 2:15 am

With the phone suggestion, remember to use it sparingly as a tool and not a crutch. Turn off the ringer and don’t look at it every couple of minutes. The purpose of a date is to spend time on your date, not check e-mail, sports scores or twitter.

4 rob May 19, 2010 at 3:14 am


they go along well with any date, it shows that you took time into preparing yourself for the event, not just a shower, shave, and throwing on some clothes. hopefully you have figured out what kind she likes, if not find a seasonal boquet.

5 Ryan Kwan May 19, 2010 at 5:17 am

This is awesome, I’m about to go on a first date today, jogging/running…great time with the article.

6 OneCitizenSpeaking May 19, 2010 at 5:29 am

Plan “B” — never leave home without it. What it you encounter car trouble; inclement weather; she has food alergies, the meal is unsatisfactory, she complains about something or she turns out to be a pain in the assets? Thinking one step ahead is key to looking cool and prepared. BTW — keep a clean blanket in the car, it does come in handy for impromptu picnics etc. should you really need a Plan “B.”

7 Peter May 19, 2010 at 5:33 am

All I got out of this was stash some green stuff in your wallet.
But in all seriousness, great article. As to the other comments, Condoms and your phone should be carried at all times, but that doesn’t necessarily mean you’re just trying to get laid or checking your phone every 5 minutes.
Flowers is kind of hit and miss. While they can be very special for the right girl, for especially attractive women I wouldn’t recommend them. The really attractive ones are used to men constantly wanting to buy them things, and sometimes see it as trying to buy their time/panties. So show her that you’re a gentleman. You’re a guy who doesn’t try to use a 20 dollar bouquet to get her in bed.

8 JBB May 19, 2010 at 5:52 am

Emergency sewing kit, just in case your shirt loses a button (you are wearing a button-down shirt on a first date, aren’t you?) or her dress has an issue (Ah! I have a safety pin: here!)

9 Patrick Salmon May 19, 2010 at 6:19 am

If/when you do the chivalrous thing and give her your sports coat, make sure you’ve checked the jacket pockets beforehand. Leaving a condom in a pocket is going to be extremely unsubtle at best. Not that you should expect your pockets to be rifled through, but it’s entirely normal for cold hands to go into the side pockets, or curiosity to be aroused by whatever’s noticeable in an inside pocket (there’s always at least one pen in my inside pocket).

10 Pipp May 19, 2010 at 7:03 am

Know where you are going! I will never forget one first date for all the wrong reasons. We were to go hiking and he picked the hike, so although I didn’t know where we were going I was better prepared. No to mention the guy didn’t really know the trail or the amount of time it would take to hike it! It was to be an afternoon hike but he picked a hard full day trail, the poor guy had no water and was not fit enough to even complete half of it. Not the inpression you want to leave for a first date.

11 The Counselor May 19, 2010 at 7:29 am

@ Rob:

Bringing flowers on a first date is generally not the best idea. While it might be a nice touch on date ten (or if you happen to be walking past a flower market during the course of your evening), bringing flowers on a first date just makes it seem like you’re trying too hard to please her. Show up looking clean and confident and that will be sufficient.

I really like OneCitizenSpeaking’s point about the importance of good planning. While no one wants to be bossed around for the evening or feel like they’re on an artificial schedule, having a definite plan will (1) make you more at ease since you won’t be constantly worrying about what to do next, and (2) will signal to your date that you’re a decisive individual who knows how to take charge of a situation. You look weak and indecisive when you have the “What do you want to do? I dunno, what do you want to do? No, you tell me what you want to do” conversation. Plus, if Plan A falls apart (as these things sometime do), you’ll only look more impressive if you’ve already made contingency arrangements.

12 Roach May 19, 2010 at 7:45 am

Taking care of yourself and the basics you’ll have on hand seems to have been covered pretty well, so something to be mindful of is your transportation. If you’re driving, make sure your car is clean (inside and out), full of gas, and you’ve got all the appropriate emergency basics. Spare tire, jumper cables, blizzard gear if that’s a threat.

If something does go wrong, being able to quickly and competently change a flat tire or the like can go a long way to leaving a good impression.

13 Matt May 19, 2010 at 7:49 am

Even if you don’t carry a full mini-sewing kit, a couple of safety pins are a fantastic idea to have in your wallet or jacket pocket all the time. I usually have a pen and notebook in one of the breast pockets of my sport coat all the time as well. It’s amazing how often you encounter the “does anybody have a pen?” moments when out and about, and it’s good to be the guy who calmly reaches into his jacket pocket rather than the one leaving his date digging through his purse.

14 Super Dave May 19, 2010 at 8:29 am

Hankie in the jacket pocket and a spare in the inside pocket. Flowers are fine if it is a real date and not just “coffee”. “Coffee” is the “Do I really want to go out on a date” pre-date. No flowers for coffee. If you get along and plan something substantial, then flowers for a for-real first date is the thing. Just don’t act like it is a big deal, as with any gift “I thought you might like these”, “they’re pretty” (implied compliment), etc. No condoms on the first date. Don’t even think about it. If you need a condom it is a hook-up, and not a first date. Just go to a bar, skip the jacket, and visit some swinger’s site instead of here.

15 Gary May 19, 2010 at 8:33 am

Why stop on date 1? Everything mentioned, as well as many of the follow up suggestions, are as perfect for date 1 with a new girl as they are on date 5,000 with your wife. Making it past the first date, or even futher along, is no excuse to get sloppy.

16 SteveR May 19, 2010 at 8:41 am

One thing or is it 2, that I bring along are a pair of small, steriling silver dessert spoons. I wrap them in a clean cloth and offer one if/when we stop for ice cream. The ladies are surprised then impressed when eating with silver rather than a common, flimsy, plastic spoon. I picked mine up at auction for $10. Well worth it and yes she does return it when finished. Just be sure to polish them regularly. Tarnish defeats the purpose.

17 Yavor May 19, 2010 at 9:06 am

Nice tips – especially the ones about the umbrella and the sports coat.


18 Terd McFinny May 19, 2010 at 9:30 am

Here’s a few things that I found handy:

* When at a resturant (or anywhere) always take note of where the restrooms are. At some point she’ll surely ask and you can look real clever already knowing and not having to ask the waiter.

* If she’s looking cold, don’t just offer your jacket. A lot of girls will just say no. Instead, go ahead and take off your jacket and while placing on her shoulders then ask if she’d like it. Then she can’t get away with saying “no thanks”.

* Carry cash is surely a must. But I had a friend who’d always carry crisp two-dollar bills on dates. It’s a slick way to pay and tip. It’s a good conversation piece, too.

@ Gary : Yes! Especially on date 5,000 with the Mrs!!

19 Steve May 19, 2010 at 9:34 am

A real gentleman also comes with an open mind. It’s impossible to accurately decide whether this woman is a perfect life companion all in the short space of a few hours, so don’t try. If you come full of expectations, you’re likely to get disappointed. It helped me to only ask this one question on a first date: do I want to go on a second date with her?

20 Jhaley May 19, 2010 at 9:34 am

A knife. This should go without saying. But every man should always have a pocket knife on him. But most people will leave it out when they are all fancied up.

21 Thornproof May 19, 2010 at 9:48 am

Shouldn’t all men have some mints handy at all times? Isn’t that what the Sinatra quote is about?

I always keep mints in the car and try to have a few old-fashioned Star Mints (the little red and white ones) in my pockets at all times when I am heading out.

22 Impulse Magazine May 19, 2010 at 9:59 am

I would include gum and cash on the list because you can’t go out on a date without these

23 Stephen May 19, 2010 at 10:04 am

I generally make it a point to keep a pack of mints in pockets. It’s really just because I like mints (not everything you carry needs to be there incase it comes in useful). It’s generally polite to offer them around if you’re having one yourself though.

24 Playstead May 19, 2010 at 10:13 am

You forgot “humility” and manners.

25 Alain Latour May 19, 2010 at 10:19 am

I’m shocked at the comments decrying the need for a condom. Having one on you doesn’t mean you’re a bastard. It doesn’t make her a slut.

26 Sasha May 19, 2010 at 10:37 am

I particularly appreciate the hankie comment. My mom gave my husband one as a gift shortly after our daughter was born. At first he didn’t really see the point of such an “old fashioned” item, but now he uses it all the time. There are always little things needing wiping, not the least of which is our daughter.

27 Dan May 19, 2010 at 10:38 am

I just got back from Europe and went on an unexpected date last night (quick motorcycle ride and then dinner) It turns out my credit card was declined because of traveling. I was so glad I had cash on me!

28 David Kinne May 19, 2010 at 10:57 am

Condoms, definitely. A gentleman doesn’t expect sex on the first date, but you must always be prepared. Always.

Flowers, no. Makes it look like you are trying too hard. An informal survey of many women friends revealed that most of them feel that way. And as one of them commented “Who wants to drag around a bunch of flowers the whole time? I just want to get to know the guy.” And forget the single rose, it’s just too cheesy. But if the date is going very well, and you happen by a flower cart, an in-flight flower purchase can be very romantic.

29 Brett McKay May 19, 2010 at 11:22 am


Mints are prominently featured, right above the Sinatra quote.


Of course. From the intro: “Below I’ve included a short list of items I recommend a well-armed gentleman having on him during a first date (or any time for that matter).”

30 Eric May 19, 2010 at 11:30 am

‘In those moments it’s not raining, an umbrella can double as a Bartitsu weapon to knock in a hooligan’s head.’
Haha I love it! Great article.

31 Jason Helzer May 19, 2010 at 11:35 am

Ever since my days in college, and the Fall and Spring formals that required formal dress, when stepping out with a lady (and now my wife), I’ve carried a small “Formal” Kit (http://www.flickr.com/photos/helz/2152840938/) in my breast pocket.

It’s basically a very small coin envelope with a few of the most basic essentials that are invaluable to keep minor issues in check. I can’t tell you how many evenings this has saved for me, my companion, or someone else attending the event.

32 Mark May 19, 2010 at 12:31 pm

I second the note on a knife. Make it a genuine Swiss Army knife and you’ll be prepared for many situations. There’s always something that needs trimming (a loose string on your sport coat perhaps?) or something that calls for a knife. Read of a man who was wanting a date with an attractive lady in his office building. He came out of work one day to find her unsuccessfully trying to start her car. He raised the hood, found her battery was corroded. Whipped out his knife and took the terminals loose, scraped off the build up, put them back up and the car started right away … and he had his date.

33 Keith Brawner May 19, 2010 at 1:22 pm

I second (third? twentieth?) the pocket knife. I cannot tell you how many things I have had to take apart, cut, open, or trim. The tweezers have rescued my wife after getting a splinter at the park, the toothpick has been used in several dining establishment restrooms, I’ve cut a string off my shirt, taken apart (and reassembled) both of our glasses, etc.

34 Torrey May 19, 2010 at 2:12 pm

I don’t necessarily think the flowers represent a man trying to hard. I think it’s a case by case basis depending on the woman. I do think you should consider her favorite flowers vs grabbing roses.

35 Steve in Maryland May 19, 2010 at 3:38 pm

Note to Mr Latour who said:

“I’m shocked at the comments decrying the need for a condom. Having one on you doesn’t mean you’re a bastard. It doesn’t make her a slut”

Actually, if sex occurs on the first date, she is probably a slut.

36 axel May 19, 2010 at 3:47 pm

I think you meant “non non non”, french “for no no no”. “Nom” means name…
Am I the only frenchman here ?

37 Lori Darlin May 19, 2010 at 3:53 pm

I give Gary the top points. Speaking from a woman’s point of view, treat every date, every encounter, as if you are on the first date. Nothing worse than feeling conned into marrying a man who morphs before your very eyes, after saying “I do.”

38 Ben May 19, 2010 at 4:56 pm

Axel – I think the “nom, nom, nom” was referring to the Internet colloquialism for eating something tasty, a la: http://4.bp.blogspot.com/_Kac9jxGkbe4/SWnxD_Thm6I/AAAAAAAAASw/aLapUNF-LU8/s400/nom-nom-nom.jpg

39 Michael May 19, 2010 at 5:07 pm

@Axel: “Nom nom nom” is based on memories of the show Sesame Street, which many Americans watched as children. The character “Cookie Monster” would make “nom nom nom” sounds as he devoured cookies.

I think I was saying the “need” for a condom is only a need if you can’t/don’t want to control yourself, and/or if you prefer sex over a long-term relationship. Yes, a lot of men will take what they can get at the time, but I’d hope most of the guys here are learning they can do better. I’ve gone as far as the “ratty underwear” gambit to prevent myself from pushing for sex too soon.

As far as “treating every date like a first date”: that certainly sounds romantic, but really the complexion of the relationship should change slightly with knowledge and experience. You wouldn’t go over to the guy’s house (even for a delicious home-cooked dinner) as a first date, would you?

40 b May 19, 2010 at 6:19 pm

Great list! Have plan B and C. Look prepared with research on eating establishments, entertainment, bars, discos museums, ect…

Steve in Maryland. Not all girls are sluts that have fun on the first date. I married one and going on 12 years.

41 Gary May 19, 2010 at 6:20 pm

I always carry a small pair of finger nail clippers. They are very useful for all sorts of things.

It is also a good idea to keep a small emergency stash in your vehicle. Things like a clean blanket, some drinking water, something small to eat (snack crackers, beef jerky, granola bar, etc.), first aid kit, etc. (you get the idea). Be sure and “rotate your stock”. It would not be considered well prepared if you pull out a pack of snack crackers, while waiting on a tow truck or whatever, and you discover that you can’t eat them because they have more hair than you.

The better you are prepared for any situation only makes it more likely that you will be perceived as a better provider/protector in a women’s eyes.

42 Josh Knowles May 19, 2010 at 7:05 pm

I know this goes against all our manly instincts… But if you’re going somewhere unfamiliar, make sure that you’ve got a print out of the directions. Google now makes this pretty straightforward. There would be nothing worse than thinking you know the way (translation: you’ve got a general idea what end of town the place is at) and then getting hopelessly lost. This only results in driving around looking and consequently being late for you dinner reservation or the start of the show, game, whatever.

I suppose if you’ve got lots of time the thing to do would be to go by yourself a day or two in advance so you know how to get there and then you can scope out things like a good place to park, somewhere to eat/drink afterwards.

RE: condom – really?! I think we could probably at least try to show some self control.

RE: flowers – maybe. Might make a good impression, might not. I would say wait till you get to know her better and get a feel for what she would like.

RE: nailclippers, pocketknife – always a good idea to keep in your car and/or on your person.

43 Larry May 19, 2010 at 7:37 pm

If you have the means and the legality, a weapon of some kind. It would really stink to be strolling along after dinner and not be able to defend you lady should you be jumped. Fisticuffs may be fine when one is on one’s own, but you want to end the threat quickly and efficiently when other lives are involved.

A pocket knife is a must. …And a Lighter. Flame and blades define the greater part of mankind’s history. One should have them on at all times.

44 John K. Patterson May 19, 2010 at 7:43 pm

I would suggest a small multitool or pocket knife. You never know when a situation will come up and you just might need it to help you out.

I really like OneCitizenSpeaking’s suggestion of a Plan B. Never hurts to have one of those.

These tips will be very helpful whenever I have a first date. Thank you kindly for posting the article, Brett.

45 Paul D. May 19, 2010 at 7:56 pm

I recommend all gentlemen carry a small flashlight. You never know if your date may have trouble seeing a menu, or if you find yourself in a dark parking lot.

46 Joe May 19, 2010 at 10:14 pm

Chap stick people,. chap stick. No girl wants to kiss sand paper lips.

A comb slipped into the breast pocket. In case of hat hair, a windy day, or if your hair got mussed up somehow, you can give yourself a touch up in the bath room.

Spare change – for parking meters, tipping a street musician, or if there is a nice romantic wishing fountain. Just make sure you don’t jangle with every step.

47 William May 20, 2010 at 12:27 am

Have a pair of jeans available for her if you decide on a hike or canoe adventure; she will love wearing your pants because females love cross-dressing and the equality it symbolizes.

48 Ruprecht May 20, 2010 at 12:33 am

Really? If we’re talking about an arsenal, a gentleman should carry a firearm. A Walther PPK or a CZ-83 would make a good pistol for carry on a first date. Depending on the locale, a classic M1911A1 or Colt Commander might be in order. A gentleman should of course be able to defend his lady.

Condoms? I daresay, we haven’t really grasped the idea of dating as seeing if the other person is suitable for marriage. Marriage. Whereupon begins intercourse. Sex with a condom is not sex. It is truly a contradiction of the meaning and purpose of sex. It is nothing more than mutual masturbation.

49 Mike Russell May 20, 2010 at 1:41 am

Bravo, @Ruprecht. This is site is supposed to be about aspiring to [gentle]manliness, not more of the omnipresent puerile sleaziness. And, yes, a gentlemen should be prepared to act lawfully and prudently to protect his lady. Avoid confrontation if at all possible, but, as legendary marksman and columnist Jeff Cooper famously observed, it’s rude to bring a knife – much less bare fists – to a gun fight… and gentlemen are *never* rude.

50 Lucas May 20, 2010 at 1:46 am

I notice that many of you disagreed with my suggestion to bring condoms, but none of you disagreed with the KY Jelly.

51 Johnny B May 20, 2010 at 1:54 am

excellent essentials list and additions, gents. i’ve got some refining to do.

52 RTRebel May 20, 2010 at 2:19 am

I’m hearing a lot good suggestions on what to bring on a first date, and I’m sure they all help, but they seem to encompass a few key principles. So I think all a guy really needs to bring into a date (or actually the entire relationship maybe) is:

Self confidence (be her jackpot)
Inner Strength (be her rock)
Security (Be her knight)
A Sense Of Humor (Be her relief)

But don’t “try” to be these things cuz that will backfire (fake it and you won’t make it), I think us guys are naturally these things deep down. if we have the courage to be completely honest with ourselves and the girls we’re after at all times, then we’ll express these things in our unique ways while just being ourselves.

53 Lewsta May 20, 2010 at 2:31 am

Lucas, having decided long ago that sex with anyone besides my wife is not an option, I would have no need for either of your “necessities”. If she was not my Wife, we’d have no need of either. If she were, we’d have no need of them either. She is not there to make ME feel good….. I am there with her to respect and honour her as a woman. Not a toy.

As to means to protect/defend her, certainly…. the every day carry piece that accompanies me when I am out should suffice. Else I’d best not be carrying it at other times; and if I carry it other times, it should serve well on a date. Unless, of course, our first date is to a firing range… in which case I could bring along other options…. and these need to be carry weapons.

54 Nadia May 20, 2010 at 3:15 am

“Steve in Maryland May 19, 2010 at 3:38 pm

Note to Mr Latour who said:

“I’m shocked at the comments decrying the need for a condom. Having one on you doesn’t mean you’re a bastard. It doesn’t make her a slut”

Actually, if sex occurs on the first date, she is probably a slut.”

…and you are a bastard (if the above). Or in terms I prefer, a lecherous jerk.
(since the legality of your birth isn’t really the question here and isn’t a matter of respect for others or self control)

55 Nadia May 20, 2010 at 3:23 am

Regarding the original suggestions:

-Lose the hankie. I would not want to blow my nose or wipe my face on someone’s handkerchief no matter how clean it *appeared*. Go with paper tissues. Sure you’ll lose that memento to remember you by effect but you could always give her the pen. ;)

-Skip the mints and get something that actually works. Ordinary sugary mints don’t really freshen breath. In fact they make it worse (because of the sugar feeding bacteria inside your mouth). Just this afternoon I saw a package of little capsules you can take that will (according to them) dramatically reduce bad breath within 15 minutes. They had sunflower and parsley oil in them. I don’t know if they work but I’m sure there are products out there that are much more effective than traditional after-dinner mints.

You could also do what I do: I carry a mini (travel size) toothbrush and toothpaste with me and visit the bathroom after meals to brush my teeth. If you visit the loo you can also check to see if you have a giant piece of parsley stuck in your front teeth. That’s not something you want your date to remember you by.

56 Mia May 20, 2010 at 3:28 am

From the first few dates with my husband, 12 years ago, these are the things that stood out and I still remember

1. Chivarly. Opening the car door, pulling out chairs, etc. Thoughtful actions are far more important than buying things. Anyone can shove money at a florist.
2. Home cooked meals. He turned up with a shopping bag of ingredients and a bag of cooking equipment, and cooked me a meal in my own kitchen. Again, the effort he went to was considerable and touching.
3. Fun dates – we actually did things – skated, bushwalked, picnicked, biked. So nice to get away from the every date is about food approach.
4. Chivarly. I know I mentioned this already, but seriously, this so rocked. No one opens car doors for anyone anymore!

I’m with the other female commentator – flowers are a pain in the arse to carry around. It’s weird to receive them before the date – feels like the giver is presenting a ticket. Personally I might buy flowers for myself, but I feel patronised receiving them from people I don’t know well – like “here’s a shiny object for you to keep you happy”.

57 MIchael May 20, 2010 at 6:35 am

I will totally agree with Mia.
Flowers are awkward to carry all the time and in fact make date less fun for the girl.

And going back to condoms. Two people don’t always PLAN ahead to have sex, it can happen on first date, second date or 3 months later. If You don’t refrain from sex for some reasons(moral, ethical, religious), you should ALWAYS have condom on a date.
It is the same as with sewing kit – it is about being prepared, but much much more important.
Of course condoms should be hidden so she couldn’t find them(even if she is having condoms in her purse as well(which is not so uncommon))

58 James May 20, 2010 at 8:23 am

Excellent article, with some good follow-up comments.

The only suggestion I would offer here is re: “First, jeans, a button down shirt and a sports coat is a can’t fail look to impress your date and help you look your best. ”

NO. You will spectacularly fail in your effort to look your gentlemanly best if you commingle denim with, well, anything remotely dressy. There is perhaps nothing worse in the sartorial universe than forgetting to put on slacks that are proportinate to the button down shirt and sports coat that you’ve (appropriately) hung on your shoulders. There’s more than a few women that woudn’t mind the jeans and jacket look, or understand how wrong it actually is, so it is up to the best among us to present a picture of ourselves that is complete and correct.

That we shouldn’t take our fashion cues from Hollywood and NYC hipsters should not need to be noted here.

59 Mark May 20, 2010 at 8:35 am

Steve in Maryland is right, if she has sex on the first date she is acting slutty. Nadia,the man is not a Bastard because the woman is a slut, but if he forces himself on her, then he’s a rapist and deserves public execution. Also a man should be armed with at least a high quality pistol on a date or alone. If you live where you aren’t allowed to go armed, MOVE…

60 Dan May 20, 2010 at 8:47 am

Sports coat and button-down shirt are a great suggestion. But jeans? Jeans are the ultimate dumpy look, but probably suit most men in this country well, and so appeal to the type of woman who’d go out with such bozos. But, wait a minute…. You forgot to mention the dusty pink baseball cap, evidencing an MBA in finance. Sunday morning in New Canaan and Darien, CT is always dip-stick-watching season as investment bankers (“bankers”) drive their Porsche’s and similar at dangerous speeds up to 40 mph to buy the Sunday paper and bagels, really impressing everyone as you can imagine. These goofballs wouldn’t be caught dead out driving about without a dusty baseball cap with an embroidered logo attesting to their attendance at some cretinous power conference in Idaho. No young parasite should be without a shelf full of such caps to wear on dates. Another tip: Forget putting you Blackberry on silent mode, since all important deal-makers are always getting up from the table to take calls, particularly in trendy restaurants around New Canaan and Darien. And remember to jut your elbow out as far as you can while pacing about on the phone so everybody knows you’re working on a really big deal. This will really impress your date, and all the patrons, too. Remember to never shave on weekends, so everyone and your date immediately think of you as a little bit sassy and the perennial grad student studying for the big one. And always walk around town like you’re taking in the locals with condescending amusement at the very idea they don’t recognize you for the important “banker” you are.

61 Geoffrey Cubbage May 20, 2010 at 10:00 am

Some great pointers here in both the article and the comments section, but I’m surprised no one has mentioned a watch yet. Flipping your cell phone out to check the time makes you look like a harried banker working after-hours; nudging a shirt cuff back (or better still, producing an understated pocket watch) simply shows you to be a thoughtful and well-prepared gentleman.

62 Ted May 20, 2010 at 10:02 am

I always carry a few things not mentioned in the main article. 1 – the brightest tiny flashlight you can find, usually one that fits on a key ring. I can’t remember how many times it was used to find something (lipstick) that fell under the table in a dark nightclub. also there is a restaurant that is so dark, we’ve had to use it to read the menu (nearby guests asked of they could have a turn when we finished. 2 – a butane “torch” style lighter. Even if your date doesn’t smoke, you may end up out with friends who do. Also great for lighting candles; every girl I’ve ever dated always had a bunch of candles at her place. 3 – multi-tool or Swiss Army Knife. One that has a corkscrew is a plus for opening wine. 4 – if you are in a steady relationship, give each other a spare set of the other persons car keys. If you or your date locks the keys in the car, or loses them, you don’t have to sit around for hours waiting for the auto club or locksmith, etc. My carrying a spare set of keys for my girlfriend’s car saved the day more than once. Also, if you have to run out to the car to get something or store something, either one can do it. Also if you have to pick up their car for some reason. 5 – information about the destination. Things like, is there a cover charge, hours of operation, where is parking available, dress codes, metal detectors in use, specials and discounts, when does it get too crowded to park or get in, what is the surrounding neighborhood like, etc.

63 Snarly Gawleth May 20, 2010 at 10:28 am

Agree with the handful of comments mentioning a small pocket firearm. There was a time when carrying something like a CZ-1945 was as much a part of a gentleman’s wardrobe as was a fine watch, cigar case, and flask. Those times have changed but the need to have a firearm to defend oneself and one’s lady (hopefully as a last resort / deterrent) has not. Nowdays there are many 380′s and 9mm’s that are about the same size as the old pocket 25′s. Of course, get trained on safety, proficiency, situational awareness, de-escalation and conflict avoidance, rules of engagement, and aftermath, and know the laws.

It seems some of the rationale here for being a “gentleman”, and some of the comments, indicate the primary motivation is to bed down the lady as soon as possible. But this is not the M.O. of a true gentleman. His purpose is to honor, respect and protect her. Intimate relations may or may not happen on any particular timeline but the truest of gentlemen will wait for marriage since that is the most deepest respect for her. A good way to end the first date — if it went well — is at the front doorstep. Possibly even ask “may I kiss you” before moving in for the kiss.

64 Ed Roberts May 20, 2010 at 10:51 am

A note to the author: an arsenal is a factory where arms and ammunition are manufactured. An armory, in the context needed for your title, is the collection of arms or the storage place of arms and ammunition owned by an individual or an organization. The title should refer to a man’s armory, unless the intent is to discuss the manufacturing of the items listed in the article.

The article is good, and would be better if the author improved his command of the English language a little.

65 BBinKC May 20, 2010 at 11:16 am

Most of the items on this list are things a man should always have on him. Here are a couple of more items for the list:

1. A couple of bandaids. Slip them into your wallet. They work as intended when you or someone with you gets an injury. They also work great for your date to put on her heels when those fancy new shoes she bought for the datea start to rub them raw. They also serve as tape if you you need to leave a note someplace.

2. Wallet pen. Get the original silver one. I’ve had one for years and it is one of the most useful items I’ve ever owned.

3. Index cards. Take 2 or three and cut them down to the height of the largest compartment in your wallet. If you sandwich the bandaids between them it keeps them out of the way nicely. Never know when you’ll need to write a quick note. Like when she tells you her favorite color, food, flower, middle name, birthday, etc and you want to write it down on your next trip to the bathroom so you don’t forget (which you will).

4. I’ll second the safety pin suggestion. Put one large and one small one on your keychain. They come in very handy.

5. Extra car key in your wallet just in case you lock yourself out. Do you want to sit with your date and wait for AAA (you do belong to AAA right?)

6. Another vote for a flashlight. I highly recommend the Fenix LD01. Use lithium or rechargeable batteries in it or any other LED light. Alkalines have a short life in these and a steadily dropping power curve where lithium and rechargeables drop fairly to about 80% power as fast as alkaline then flatten out and hold steady until the end of their life.

66 M May 20, 2010 at 12:01 pm

@Ed Roberts

Loosen up a little. Don’t be such a jacka$$.

67 rufus13 May 20, 2010 at 12:07 pm

A compact pistol. Glock 26 or 27/Walther P99 are good date pistols when slung on a quality shoulder rig. Nothing blows a date like being mugged or getting away when your lady can’t. I don’t go anywhere (except the Courthouse) without a pistol. If the lady notices it and is outraged, that is a good indication that this is the last date. If she notices and approves, then there might be Friday “ladies night” date at the local pistol range. A well-concealed pistol won’t be noticed with a jacket on.

Thanks for the article.


68 Nathanael May 20, 2010 at 12:11 pm

I think carrying a condom smacks of an unmanly desperation. A self-confident gentleman rests assured in the knowledge that he will be able to find a woman with which to share his life (or, for those of you not so keen on marriage, a series of woman with which to share chunks of it). Thus, there’s no desperate need to squeeze in every sexual encounter possible, because regular sex is coming, he’s sure of it.
Besides, except for those with low standards or exceptional charm, most of you aren’t getting anything on the first date anyway. You’re just molding your psyche away from that of a confident gentleman into that of a desperate lecher. Women with class will pick up on that vibe and get the hell away from you. While you’re scrounging for dates and occasionally getting a woman drunk enough to sleep with you, men with more confidence and patience are in steady relationships that not only give them more sex, but a much more satisfying life.

69 Nathaniel May 20, 2010 at 12:44 pm

Who’s the bigger jerk? The guy who kindly points out a mistake in a published essay? Or the guy who calls him a jerk?

Or the guy who calls that guy a jerk? =)

70 Alex May 20, 2010 at 1:13 pm

I disagree with Mia on the cooking a meal on the first date. Now a days that is way to serious of a move to make with a lady. It will freak out most of them.

71 Sven Galli May 20, 2010 at 1:34 pm

Goodness, me! Why all you bloggers should know this:
The thing to take on that first date is YOUR MOM!!!!!
Hell’s bells, if anyone can keep you from running it into the ditch, it’s your mom. The bonus is that, in case your date is a gold-digger, your mom can sniff it out in a trice and leave the baggy sausage on the curb. Mom knows all about hankies and condoms and clean underwear and all the stuff that the “woman of today” considers important.
Mom; never leave home without her.

72 Nina May 20, 2010 at 1:37 pm

I think if any man carried all those things on a first date, I might write him off as playing for the other team.

Ick on the “hankie”. Dirty, nasty, disgusting things. If I spill anything on my clothing in a restaurant, I have a napkin and there is a ladies’ room. If you’re taking me out to dinner and the venue includes neither napkins or a ladies’ room, I’ve already ended the date.

Mints are a good idea for anyone, anytime.

Carrying an umbrella with you if it really isn’t necessary is, well, sort of a wimpy move. It’s pessimistic, too. You should really only carry an umbrella around with you if you live in a climate that requires it or if the weather at the time requires it. If you want to stick an umbrella in the trunk of your car, that’s fine, but don’t carry it around if it isn’t called for. A decent restaurant should have a concierge and/or valet, anyway.

Cash is a good idea for both parties, although you’re wrong about parking and cabs — in my city fewer and fewer meters accept cash, so you’d better have a functioning credit card or a meter card. Most cabs take credit cards, too. Still, all of us should probably keep emergency cash with us, especially if we’re out late at night.

A “sports coat” ? Use of that phrase alone is a deal breaker.

Actually, being sort of calculatedly manipulative about this sort of stuff is very, very creepy, and women are on to this carefully planned fake charm. More often than not, this is the sort of stuff men use to lure women into very controlling, abusive relationships.

The best thing you can bring on your first date is your genuine self, openness, honesty, spontenaity, curiosity, enthusiam and general good manners. Just be yourself.

73 James May 20, 2010 at 2:23 pm

“A ‘sports coat’? Use of that phrase alone is a deal breaker.”


We live in the age of the Common Man, populated by guys who wear t-shirts and baggy shorts anywhere and everywhere…guys who too often comport themselves in a manner proprotinate to their wardrobe choices. I would think that any effort and/or willingness on the part of some men to look presentable and respectible, to include wearing a (gasp!) “sports coat”, would be something to applaud.

74 ajkurp May 20, 2010 at 2:28 pm

1911 and 2 extra mags.

75 Nina May 20, 2010 at 2:31 pm

If you use that phrase, you’re too old for me, is why.

Anyways, you all do realize you all sound incredibly gay, right — or is that the point — after reading through a few articles I get the impression this is some kind of stupid satire site or some kind of “coded” gay site.

The one startling fact I definitely come away with is women are things, objects. To y’all, they’re not distinct individuals with minds or personalities of their own.

I actually feel sick reading through this. Seriously. There’s something deeply unhealthy and disturbing about this site.

76 Nina May 20, 2010 at 2:34 pm

If you use the phrase “sports coat” you’re old and decrepit.

You can dress appropriately without being a prissy, priggish, simpering douche about it.

Anyways, this site is seriously creeping my out now, like it’s some weird “coded” site for something else altogether.

The one clear, startlingly clear, fact I come away with is the people who run and frequent this site see women as objects, things, rather than as human beings with minds and souls and hearts and personalities of their own.

77 Michael May 20, 2010 at 3:39 pm

I find it very interesting that somebody can get this website so absolutely wrong. Can You please tell how did you stumbled upon this website?

> Just be yourself.
I’m totally sure that being himself is the last thing you really expect from a man.

78 James May 20, 2010 at 4:10 pm

Thank you, Nina, and may we never darken each other’s doorways.

79 Sarah May 20, 2010 at 4:17 pm

I am a woman who loves this site and appreciates a community of men genuinely concerned with higher standards of personal conduct and intellect. It is irritatingly short-sighted to consider a man’s thoughtfulness or preparedness to be “gay.” How often do women spend hours dressing and preparing for a first date–considering what food she’ll order (that’s actually completely annoying) or what she’ll discuss or disclose? Why the double standard?

Certainly men shouldn’t be fake or creepy but to be courteous and respectful should be a baseline. If she looks down on you for being decent, she’s not worth it.

And please don’t carry a firearm on a date.

80 Petrov May 20, 2010 at 4:28 pm

Steve in MaryLand – You are so right. If a girl does humpty-dumpty on the first date, she’s a slut. Worthless. I work with many of these kind of women and honestly, most of them have very little self-respect and low esteem. If a girl has sex on the first date, just think how many other Tom, Dick and Harry’s she’s going to sleep with (or already has).

81 Krakondack May 20, 2010 at 4:28 pm

There’s such a thing as being over-prepared too. For examplearrying extra feminine hygiege products in your coat pocket would strike me as wierd.

82 Nadia May 20, 2010 at 5:19 pm

@ Mark May 20, 2010 at 8:35 am (Comment #59)

You said:
“Steve in Maryland is right, if she has sex on the first date she is acting slutty. Nadia,the man is not a Bastard because the woman is a slut, but if he forces himself on her, then he’s a rapist and deserves public execution. Also a man should be armed with at least a high quality pistol on a date or alone. If you live where you aren’t allowed to go armed, MOVE…”

My point was that if *she’s* a slut for sleeping with him on the first date, then *he’s* just as much of a slut. (or lech, which is a more popular term in my part of the world)
Let’s avoid the double standard, okay? Maybe you didn’t mean to sound that way; in that case, I apologize for mischaracterizing you. The ‘easy woman=bad, easy man=good’ idea still seems to crop up now and again and it’s a particularly offensive (and stupid) belief, imho.

To change the subject a little, I was wondering why you’d think it was so important for you (or “a man”) to bring a pistol on a date? Are we really that scary….? ;)
Joke aside, what is the rationale for *needing* a deadly weapon at all times?

83 Nina May 20, 2010 at 5:39 pm

How did I get the impression I did about this site?

It’s all SO self-obsessed — it’s all about creating this big fake facade to lure some poor, helpless, delicate little female into your life.

And it’s gay because real men — like the one I’m married to — don’t hang out on internet forums discussing their wardrobes with other men — they have real jobs and families and real interests.

This entire site is about the pretense of manliness, not the art of manliness.

You’re either a man or you’re not and it has NOTHING to do with your outfit or your shave cream or hiding behind a gun or knife collection.

What woman agonizes over ordering food or discussion topics, or, for that matter, her outfit — sure, you want to look nice, but it doesn’t take THAT long to shower, put a touch of makeup on (unless you’re trowelling it on or something, I guess, in which case, eeuuww)?

Are the women who are attracted to this kind of superficiality equally as superficial? How do you even know who the other person is if you’re obsessing over yourself or if you’re both fixated on the image you’re going to project in the hopes of getting something in return?

I don’t know a single lasting relationship that began with this kind of shallow pretense. Sticking a “hankie” in your “sports coat” to impress the little lady and have something to dab away at her as if she’s too infantile to excuse herself, go to the ladies’ room and fix a spot of wine on her blouse or whatever does not make you a man. The visual that conjures up is revolting.

This really is just Godless and disgusting and objectifying. Why don’t you just put on your “sports coat”, tuck a “hankie” in your pocket and pick up a blow up doll at the porn store — you’ll get exactly what you want from a woman and you’ll actually get some use out of that “hankie”. (“Hankie”?? What kind of self-respecting man even uses a word like “hankie” in 2010?? )

And what kind of self-respecting, genuine woman is fooled by all this pretense and fakery and superficiality?

This is really and truly the most Godless, narcissistic, creepy stuff I’ve seen in a long time. Seriously. Skin-crawlingly, disturbingly, revoltingly creepy and Godless.

84 Michael May 20, 2010 at 6:18 pm

@Nadia – I must admit that I don’t understand the need for the gun too. It is more resonable to plan the date in safer part of the town than to bring a gun. That’s is one thing. Second – I can bet than many, many manly man shown at this site did not taken gun to every date. While man should not reject weapon as a useful tool, he also should not feel obligated to carry one all the time. And third thing – guns, along with religion, politics, and other controversial subjects EVER should be a part of a first date. And stating that “If the girl don’t like me caring gun it is the last date” is simply stupid. On first date one don’t really know and trust the other person, and even if the girl have nothing against the guns, she will be a bit worried if you bring it along. The same is with politics/religion – even if girl has same life viewpoint as you, it is not good to talk about it on first date. I collect knives and old foto equipment – gues what I would rather talk about on first date?

@Nina – And it’s gay because real men — like the one I’m married to — don’t hang out on internet forums discussing their wardrobes with other men — they have real jobs and families and real interests.

Real interests? Oh, please, do tell.

85 Nathanael May 20, 2010 at 6:27 pm

Crickey, Nina! If this is “really and truly the most Godless, narcissistic, creepy stuff I’ve seen in a long time,” you aren’t getting out much, are you?

This is an internet forum, and every internet forum I’ve ever seen has its share of Godless, narcissistic and creepy, probably because people tend to have a fair share of Godless, narcissistic and creepy in them. That said, there’s some good stuff on this site, and the community does a fair job of self-policing.

As to some of your objections: one can focus on dress to the point of narcissism, but some attention to it is important. Clothing is not only for utility, but is also part of the social nature of man, clothing is communicative. Dressing in a sport coat communicates something different to your date than jeans and t-shirt.

Also, habit, narrative and imagination are extremely important to human character (see Aristotle, MacIntyre, and Burke). To a large extent we become what we imagine. If you want well-dressed, polite, prepared men, they will have to have an image and interior narrative that corresponds to that and cultivate habits to put it into practice. This site can help with that.

Many of the posts on this site are concerned with smaller virtues, perhaps, but they are virtues nonetheless.

86 Christy May 20, 2010 at 6:57 pm

Wow ~ after reading all of these posts, I must say I am impressed for the most part. I would love to have a date with a guy who actually put some thought into preparation and appearance.

As for Nina, bless your heart ~ you really sound like you are carting around a cinder block on your shoulder. I would think that someone with such a “real man” as you, would convey more happiness and contentment ~ and a little less criticism.

One more little thing Nina ~ hurling insults is not impressive.

87 Nina May 20, 2010 at 6:57 pm

Real interests, “Michael”?

Being a good husband and a good father and a good son. Providing for a family, raising five children, taking care of his very elderly parents, including a father with Alzheimer’s.

How’s that for a start? Are you man enough for that?

Are you man enough to sacrifice your pretty “hankie” collection so your kids have what they need, or so you can put all five of them through college without borrowing money or burdening them with loans? Man enough for that, Michael?

Are you man enough to forego your designer shave soap and your cologne and your snazzy “sports coat” because your son needed life saving surgery? Man enough, Mikey-poo?

Do you have what it takes to sit vigil over a sick child’s bed? To change your father’s clothes when he has an accident? To push your mother’s wheelchair?

Or are you too busy picking out the “right” shirt and rehearsing your oh-so-witty dinner conversation to bother with such distasteful things?

Practicing dessert pairings and witty banter doesn’t make you man.

Getting up at three in the morning even when you’re drop-freaking-dead exhausted from a fifteen hour work day to comfort a child makes you a man.

How dare you question my husband? How dare you, you effeminate, prissy, little fairy — you wouldn’t know what a real man was if you met him face to face in the street. Or if you did, you’d piss yourself fumbling to unwrap your purse derringer from your “hankie” in a pathetic attempt to impress the shallow, empty-headed skank you just took out on your big date.

88 Nina May 20, 2010 at 6:59 pm

Christy, given the only “man” you have requires two AA batteries, you’re not really one to criticize — and you can’t hurl insults while whining about someone else hurling insults, you hypocrite.

89 Youngling May 20, 2010 at 7:09 pm

You should definitely wait on flowers, because you never know if your date might be allergic to pollen. And having to take her to the hospital for an allergic reaction wouldn’t be fun for either of you.

90 nemo May 20, 2010 at 7:20 pm

Condoms? Gentleman? Perhaps you should have some petrolium jelly for your dates new tattoo! And some tetracycline .

91 Nathanael May 20, 2010 at 8:00 pm

“Christy, given the only “man” you have requires two AA batteries, you’re not really one to criticize.”

Methinks this site just became a bit more Godless and creepy…
Nina, if your husband is all that you say, why are you so determined to piss all over everyone on this site? Why should the wife of such a wonderful man be going out of her way to start flame wars about manliness?

92 tom May 20, 2010 at 8:02 pm

hey nina

this article was ‘what to carry on a first date’ it’s not for a married couple. why are you even on this site? i feel sorry for your husband. sounds whipped.

93 Nathanael May 20, 2010 at 8:11 pm

Nina, I would suggest this article (http://artofmanliness.com/2009/09/27/being-the-rock/) as a good example of this site taking on a topic more important than miscellaneous items that might be helpful on a first date. This site contains a lot of content, some more serious in nature than others, and I doubt anyone on here would say that pocket handkerchiefs are anywhere near as important as caring for the family in a crisis, but that hardly means that we should never discuss pocket handkerchiefs or other such things.

94 Gaviota May 20, 2010 at 8:36 pm

Nina, why are you verbally attacking complete strangers, none of whom has bothered you? Each one of your posts has sequentially become more shrill, more hostile, and more abusive. When it comes to first dates, I’d say you’ve failed yours here, and failed spectacularly. Have a nice life, lady. Goodbye.

95 tomdawg May 20, 2010 at 9:21 pm

Take a GUN, always…if you encounter crazy bwitches like those posing here.

96 Doktor Jeep May 20, 2010 at 9:31 pm

What, no gun?

97 Brett McKay May 20, 2010 at 9:41 pm

@Ed Roberts-

The definition of arsenal:

1. A governmental establishment for the storing, development, manufacturing, testing, or repairing of arms, ammunition, and other war materiel.
2. A stock of weapons.
3. A store or supply

It is of course definition number 3 being used here. It is perhaps you who needs some brushing up on the English language.

98 Carl May 20, 2010 at 10:13 pm

@ Nina- Are you serious? It’s gotten to the point where your posts are so pathetic that I don’t think they can be serious. If what you say about your husband is true- More power to him. I respect that. Maybe you should be helping him, instead of wasting your time insulting people you have never met on a forum you clearly don’t understand.

99 epsi1on May 20, 2010 at 10:14 pm

I can’t help but feel that there are a lot of issues with this guide, and also with people’s comments.

Part of it may just be a generational thing. I’m 24. I wouldn’t think of going on a date without bringing a condom. It’s a matter of consideration in this day and age. I agree that it’s usually a better sign to wait a little while, but sometimes things happen. Chemistry does actually exist and if you’ve spent the night dancing and having drinks, things can happen. It’s far better to be prepared than to open one another up to any risks there may be.

The number of people advocating carrying firearms on dates… well that just confuses me. I have never been on a date where I have felt the need to be armed. Even with a blade. Maybe it’s because I’m a bigger guy, or who knows what, but if you’re taking a woman out somewhere that you don’t think you can protect her without firearms, you’re making a poor decision. If you happen to choose to carry a gun on a regular basis, that’s fine, it’s your decision, but it should never be a “required” item.

There are also a number of other posts that are just a bit to cliched and contrived. Most women I know don’t appreciate that kind of thing. They like spontaneity, carrying around items just so you can be the “white knight” who saves their evening…? Come on. If you’re interesting, funny, clean, and well dressed you’ll have already done well enough, even if they do get a stain on their dress. Though even then you still might not get a second date.

All of this just seems like too much striving and not enough confidence and being one’s own self. That’s by far the real key in a first date.

100 Brett McKay May 20, 2010 at 11:28 pm

Don’t feed the Nina troll. Had I not been traveling the last couple of days I would have deleted her comments. Since so many responded though, I’ll just leave them. But there’s no need to continue the “dialogue.”


I don’t think confidence/being yourself is mutually exclusive with being prepared to be well-mannered. Nor do I see how these gestures could be seen as “contrived.” Offering a woman a handkerchief if she gets something on herself or having an umbrella in your car are pretty natural things to do. And wearing a sports jacket and carrying some mints are quite normal as well. I think these gestures would only seem artificial if you’re typically a genuine cad or you go overboard with the gentleman thing and try to be all flowery and knightly about it. For a confident man, these things go as smoothly as butter.


Our fashion expert, Antonio Centeno approves of the jeans and sports jacket look. If you’re a regular reader, you know he is far from being a NYC guy or a hipster, but is a master and champion of traditional and classic style. Unless you’re going to a fancy restaurant (which you shouldn’t be doing on a first date anyway) wearing formal trousers with a sports jacket is going to look too stiff and formal and will probably make your date feel under-dressed.

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