Road Map to the Perfect First Date

by Brett & Kate McKay on December 13, 2009 · 130 comments

in Dating, Relationships & Family


So, you’ve decided to stop hanging out with women and start dating them? Bully for you! Now you must take on that ever-intimidating first date.  While a first date can be a road fraught with obstacles and snafus, when you have the proper guide, you can make it go off without a hitch. To help you not only get through your first date with a woman, but also enjoy it, we provide the following road map.


getting ready

Plan. Women are suckers for a man with a plan because it shows you have initiative, can think ahead, and aren’t shy about taking the lead. Don’t punt and ask her what she wants to do. Be a man! You’re the one doing the asking, so it’s your duty to come up with something that she’ll enjoy. When a woman is with a man that has a plan, they feel they can relax and really enjoy themselves.

Clean the car. If you’re picking her up in your car, give it a nice cleaning before the date. First impressions matter big time on the first date, and women will check you like a drill sergeant at bunk inspection. Many women will use the cleanliness of your car to gauge how you carry yourself in the rest of your life. If you have empty 32 oz Big Gulp cups, old clothes strewn out in the back, and food crumbs everywhere, your date will assume your house is even messier and that you’re generally a slob during the rest of the week. Not a good first impression.

Also, you might not notice, but your car probably smells. Leaving sweaty gym bags or Saturday morning’s fish catch in a car causes odor to build up in the upholstery. Spare your date the olfactory torture by airing out your car and spraying it down with Febreeze.

Just give the car a quick wash, vacuum it out, and wipe down the vinyl. It will probably take an hour or so, but you’ll be left with a car that will impress your date, even if it’s a 89′ Honda Civic.

Get some cash. Stop by the ATM and pick up some cash. It’s good for greasing palms during the evening, but you’ll also need it to pay for parking and other incidentals.

Dress up to show respect. Dressing up not only leaves a good first impression, it’s just plain respectful. It shows your date you thought enough about them to put your best foot forward. When you show up in a pair of jeans and a t-shirt, it’s like telling your date, “Eh… I had nothing better do so I just came over in what I was wearing.” Even if you’ve planned a casual date, put on something dressy casual. No need to bust out a tie. Go for something like a pair of jeans, a button down shirt, a corduroy blazer and a nice pair of boots (shined, of course).

Call her and tell her exactly what you’re going to do on the date. While you might not think about getting ready for your date until a few hours before you pick her up, a lady likes to plan ahead and think about what she’ll wear and how she’ll do her nails.

Show your date that you have some gentlemanly forethought by calling a few days in advance and telling her exactly what you plan on doing with her. This will help her decide how she should dress and make herself up. Women really dislike being dressed inappropriately for the occasion.

Moreover, by knowing what you two will be doing together, your date will feel more comfortable and relaxed which results in her having a good time. Wait for the surprises after you get to know each other better.

The Pickup


Be on time. As my grandpa says, “A gentleman never keeps a lady waiting.” Arriving late shows disrespect and only creates unneeded anxiety in a woman. If you’re running late because of unforeseen circumstances, call your date and let her know your estimated time of arrival.

Also, don’t show up too early. In my experience, women will use every available minute they have to get ready. Don’t piss your date off by showing up 15 minutes early while she’s still in her bathrobe. You’ll only embarrass her because you caught her without her best face on and now she’ll feel pressured to rush getting ready because you’re sitting on the couch. Trust me. That’s not a good way to start off the date.

Come to the door. Only a jackass would honk.

Immediately compliment the way she looks. Most women spend a lot of time and dough prepping for a first date. Let her know that you appreciate it by complimenting her. Don’t hesitate to do it, either. It should be the first thing you do when you walk into the house. Suggested compliments: “You look stunning!” or “That dress looks marvelous on you.”

Open the car door for her. Show your date some old-fashioned chivalry by opening the car door for her. Offer her your hand for support as she slides into the car. Ensure all arms and hemlines are safely inside the car before you shut the door.

The Drive


Instead of music, try talking. Remember: first dates are for getting to know a woman. There’s no better way to do get to know someone than by talking with them. The radio can act as a crutch to avoid awkward moments of silence. If you have music on, both you and your date will probably do more listening than talking. Force yourself to converse with your date by leaving the music off.

If you play music, play it softly and keep the list classy. AC/DC’s “You Shook Me All Night Long” or Sir-Mix-A-Lot’s “Baby Got Back” are not appropriate. Stick with some classic jazz or crooners like Frank Sinatra or Bobby Darrin. The music is pleasant, warm, and doesn’t distract from conversation. Remember to keep the volume down so you can hear each other talk.

Oh, and don’t play NPR either. Sure, it will make you look “smart” and “enlightened,” but talk radio will kill the conversation between you two. Make a date with Terry Gross when you’re alone in the car and stuck in traffic.

If you’re taking a cab… you should open the door for her, give the cabbie the directions, and pay.

The Date


No movies. We said before and we’ll say it again: the point of a first date is to get to know the person. You can’t do this while you’re both staring at a movie screen.

Keep it simple. You’re not proposing to her, so there’s no need to go overboard on the first date. Keep the first date light, fun, and romantic. You can’t go wrong with dinner and an evening at an art museum. Both activities allow you ample opportunities to talk and get to know each other.

You Pay. No questions. If she offers, just smile, say, “It’s my pleasure,” and hand the waiter your card.

The Door


Walk her to the door. You want to see that she gets safely into her place, and it’s just plain chivalrous. As you walk to the door, offer her your arm. It’s a non-threatening way to initiate body contact without seeming like a perve.

Make your move? There’s no hard or fast rule on whether you should kiss on the first date. Just remember that women put a lot of meaning into a kiss, so don’t go for it if you don’t plan on pursuing a relationship. You just risk confusing and hurting your date.

But if you feel like a kiss is in order, go for it. She might give you her cheek, but that’s alright. Just roll with it and play it like it twern’t nothing. There’s always next time.

You can never go wrong with a hug. Unless it’s a side hug.

Don’t go into her house. First, don’t ask if you can come in. It’s just sleazy.

If she asks, decline. Why? It shows you’re a gentleman, and she’ll respect you even more. More importantly, it’s anticipation that creates romantic sparks (this is why chicks are nuts about those Twilight books). Leave her wanting more.



Call her the next day. We’ve all probably heard those dumb rules about waiting a day and then a day before calling a woman you took out on a first date. Forget them. Just call the next day. Thank her for a lovely evening and if things clicked for you two, ask for a second date.

If she’s not there, leave a message thanking her and ask her to call back. If she doesn’t call back within 48 hours, give another call. If she still doesn’t call back, learn to take a hint and pursue other options.

And absolutely under no circumstances does a man text, Facebook or Twitter their date to follow up with them. Be a man, pick up the phone, and give her a call.

Any other first date tips? Share them with us in the comments!

{ 128 comments… read them below or add one }

101 Liz March 28, 2010 at 11:45 pm

This is fabulous!!

I do have two, related, suggestions. First, the thing about how cars can smell funny — this is true, but please be careful with the Febreeze, air fresheners, etc. As a woman with migraines, I can tell you that I ban all such stuff from my house, and dousing your car in it will end a date early because I will come down with a migraine. Which brings me to point number two: go easy on the cologne! Same problem. I personally would prefer the slightest hint of french fries from your lunch in the car yesterday to having to ask you to take me home early!

102 Patrick April 5, 2010 at 1:10 am

These are pretty solid words,
but it does not include such situations as when she insists on driving herself / both of us.
Which is fine I suppose, but how / what rules are changed if at all?
My date was rather proud of her 07 Jag ( and should be it’s amazing ) and wanted to drive us,
couldn’t see anything wrong with that though it put me a little off balance.

103 Michelle April 12, 2010 at 5:49 pm

Every man in the country should read this. Preferably several times over.

104 Alemus April 22, 2010 at 1:08 pm

A decent article, all things considered, but a disagree on one point. The choice of music should feel natural and appropriate. I would never play anything I wouldn’t enjoy by myself because it smacks of trying too hard to impress. This doesn’t mean I’m going to roll up to her house blaring gangsta rap or death metal, but playing the Rat Pack or Miles Davis if my tastes and personal style doesn’t match the music comes across as phony. Don’t play argentinian tango if you don’t even know who Astor Piazolla is.

The principles are solid, but some of the specific recommendations are a little outdated.

105 Regina April 23, 2010 at 2:20 pm

I thought musical taste would make or break a relationship too. However, I ended up marrying a man who listens to country, but I listen to classic rock. You can’t let such a small thing stand between you and another person.
And on a first date, you’re probably not going to know what particular songs a person might like, so if I were you, I would shy away from making your date a cd.

106 Nigel April 29, 2010 at 5:46 pm

I agree with the majority of this advice with a couple possible exceptions.

About opening car doors, I used to think I should always open them but have had many women tell methey think it’s cheesy and out-dated. That they would rather do it themselves. Plus things could get a bit awkward considering everybody has keyless entry these days.

As for music, I’m a musician who takes music very seriously and I listen to everything from Elvis Pressley to Slayer. For obvious reasons you don’t want to go with anything to fast or heavy but I think some alt-country, most Ryan Adams for instance, played at a moderate volume would work really well.

My two cents. Great article.

107 Mark May 5, 2010 at 9:50 pm

I would also add to this the suggestion that men leave their cell phones and beepers at home or work. Nothing tells a woman that you are not attentive as the ringing of a phone or beeper that has to be answered. Also, leave your business at home or at the office and give her your full attention.

108 yohami May 17, 2010 at 1:09 pm

Consider that once shes done with this polite guy, she will be chasing some jerk who only wants to get into her pants, and he will get some.

109 yohami May 17, 2010 at 1:12 pm

Scratch the pleasing her frame. Hopefully you picked a girl who can dig and like what you like, it being hard rock or whatever you love. When on a date, pick anything you love and share it. Have a wonderul time that is fun for YOU, and share it with her. If she doesnt seem to enjoy it, you casted her wrong. Next.

110 Rick May 17, 2010 at 11:05 pm

Great article! There are some excellent pointers here for any man trying to plan a first date. I notice some of you are scoffing and cricitizing, pointing out how you’d rather play whatever music you like, or how you don’t want to open the car door and so on. To you, I say: read this article again, then read it again. This isn’t about you trying to show off like a peacock. You’ve got to have some finesse; show restraint and let her do some of the talking and tell you what she likes. Based on her input, you can decide if another date may be in the future. You see what I mean? You keep it simple and understated, and she’ll probably be much more likely to open up and give her opinions on whatever it is you choose to talk about. Then you’re really getting to know her, and not just waiting for her to shut up so you can play this awesome song you downloaded the other day.

You might feel like a dork at first because you’ve never had to be considerate on that level before, but believe me, there aren’t many women in the world who are revolted by an attentive, chivalrous and mature-acting man. Such easygoing authority is usually quite appealing to women. If she is repulsed by these attributes, then it sounds like you’re about to spend the evening with a little girl, and you may want to forget about a second outing with her.

Arguing that this article is no good or is outdated is fine if you don’t want to change how you already are. But if you’re thinking of changing the league you socialize in, this little guide is a fine place to start.

111 Lee May 20, 2010 at 11:33 am

I find it interesting that the women who’ve commented on this article seem, one and all, to be possessed of perfect confidence and aplomb, deigning to advise us lesser creatures as to ways not only to succeed with them but to succeed with all women everywhere. This condescension may or may not be an affectation. If it’s not, it brims with conceit. You’d never dream that many women, like many men, are ordinary and unremarkable persons.

I don’t disagree with the advice given here. I’m sure it’s quite good. Indeed, of the twenty-nine dating rules with which I’m familiar, I violated one of them on my most recent date, rule #27, and quickly paid the price. Yet run of the mill men and women somehow manage to find one another and some even stay together, I don’t know how they do it.. Perhaps their secret lies in that they’ve somehow managed to get over themselves.

112 Livingstone July 5, 2010 at 12:40 am

Well, I’ve been following this site for several months now. Haven’t dated for several months either. Met a woman recently that has greatly sparked my interest.

I decided to get on here and see what I could find about “first date” advice. I tend to strongly lean toward “old-fashioned” ideals, so this was very harmonious for me. Of course, if these ideas never went out of fashion to begin with, it wouldn’t be considered just “old fashioned”…

So, I loved it. All of it. A lot of it I already adhere to, and a few things I’ll add to my knightly satchel. Very grateful for that. After reading all the comments though, one of the great bonuses has been all the women that commented in great favor to it also. I think they ALL did!

This makes it quite simple now! Thanks for your input ladies.

Great article! Now- to get that date! :-)

113 Laura July 12, 2010 at 10:32 pm

This article is absolutely, positively spot on–about everything!!
I don’t know a girl who wouldn’t be happily captivated by a man who comports himself this way.
I wish all men would read this one!

114 Jonathan D August 2, 2010 at 6:01 am

I love this article and AOM, please keep on writing to teach me and the newer generations! The situation is, I want to date this girl I went to my senior Prom with, my question is what type of first date should it be for a girl you know pretty well?
Please and thank you.

115 Honda Enoch August 18, 2010 at 4:54 pm

One question about flowers is this. We always use the word “flowers” but what if you just take one flower? A single rose, or carnation. Would that make any difference in the “your trying too hard” vs the” it’s a romantic thing to do” debate?

116 Rune September 23, 2012 at 5:22 am

Homemade letter: If you want to thank the lady for the date or ask her out on a date, you can also make a homemade letter. Many ladies love it to see that you actually spent time making a letter instead of writing it on the computer and print it out.

The recipe is as follows:
- Use 3 to 4 teabags in a deep roasting pan and add hot water.
- After the tea has mixed inn with the water put plain white writing paper into the water and make sure it is completely soaked.
- Let it stay in the water for about 20 min and then take it out and hang it up so that it can dry.
And there you go! A paper with a nice colour on it pluss if you then use some time to write the letter in a way so that she can understand what you are writing, that is big bonus. Also if you paint symbols or markings on the edges to make it look more smashing, go for it. Nothing says “I like you” more than a homemade letter that one can clearly see you used a lot of time on ;).

yep… that should be it if I can remember correctly.

117 Bella January 10, 2013 at 10:06 am

Love it! Any guy who does this for his first date is definitely a winner in my book!

118 Chris March 10, 2013 at 6:06 am

Its called Role Revision! I have female do all that with with..** Female please take note: If you want a date with a nice genuine guy, you better read this article

119 Rebecca March 30, 2013 at 7:25 pm

I agree with the lion’s share of the above, but do have a couple cents to throw in from one lady’s perspective…

Women, just like men, are all unique individuals. By all means, have a structured plan of attack for how to approach dating us, but also allow that you are going to have to be flexible enough to tailor your approach to the woman at hand. If you don’t make the effort to do so, any woman worth your time is not going to find you worth hers.

Ex 1- I personally find it kind of arrogant if a man tries to plan what a *first* date will consist of without consulting with me as far as what I would like to do, and then mutually agreeing upon what we would both enjoy. It shows that he respects me, and that we are showing signs of being able to communicate effectively even at such an early juncture. I mean really, if two people can’t even agree on what to do on a first date, they really have no business dating each other in the first place.

Ex 2- I have an absolute rule that on a *first* date, if you want to pay for a drink or a cup of coffee, that’s fine, but I pay my own way at dinner and you pay yours. For one thing, that means I can order whatever I want (Yes, I will take the filet and 12 year old islay single-malt scotch and not the blended rail swill, thank you very much!) without feeling like I am possibly overburdening my date’s wallet or coming off as some high-maintenance princess nightmare. For another, there are plenty of men out there who think that, because they have made a financial investment in the date/woman, they are entitled to a return on that investment, be it sexual or otherwise. I am not a prostitute, and even the swankiest meal does not imbue you with eminent domain over my affections. By shutting the possibility of that expectation down, I assert that I am an independent, functional adult who determines her destiny and clearly draws her own boundaries so as to respect herself and others.

Maybe that makes me a little difficult. But if you are seeking a partner, not just a hookup, would you really rather she be that easy?

120 James April 1, 2013 at 12:22 pm

Assuming date #1 consists of drinks and is basically just a meeting, should date #2 really consist of dinner? Isn’t that too soon?

Also, is a movie really that bad for the first real date? Why else would it be such a timeless classic date idea?

121 Grace Mary April 3, 2013 at 5:11 pm

This is an amazing article. Many of this might seem like common sense to some people. It is definitely sense, however, I can say from experience that it is not at ALL common.

I have one thing to add. If a woman invites you in and you decline make it clear to her that it is not because she is unattractive. Most women, even the stunningly beautiful, could be a model, ones have low self-esteem. Be nice.

122 Miss D May 10, 2013 at 2:46 pm

I have no allergies and no problems with things smelling nice so I would much rather you have some good smelling scents than the last person who posted about migraines (which I agree is a perfect way to end a date). The only thing that I would suggest is calling ahead and asking her if she has any sensitivities to fragrances! I think that’s not only the most considerate thing to do but it also shows you’re smart and not afraid to talk to me before a date! It should be easy to ask and then maybe she may even drop some hints as to what her favorite scents are, or favorite flowers (or if she’s allergic to them)

I should be a gentleman :)

123 Nathan H May 21, 2013 at 9:26 pm

How would one decline her if she does invite you in? I understand the gentlemanly intention but I am confused on how to deliver without offending.

124 Ricardo R. October 3, 2013 at 10:18 pm

I really enjoyed this article but as a young man (19) I would suggest a follow up text that same night simply saying “I had a great time, goodnight” or something along those lines. something short and lets her know you’re thinking about her. and then that call would happen the next day, hopefully about a future date

125 James J. October 25, 2013 at 9:01 pm

One of the lines reads, “If she asks [to come in], decline.” What would be a gentlemanly way to decline her offer? I’m 20, so if she asks me to come in, it’s probably so that I can meet with her parents. If I decline, wouldn’t it seem like I’m telling her that I’m too pusillanimous to meet her parents?

126 Perry December 21, 2013 at 5:22 pm

Most of my dates were movie dates.

Last one was a ghost story. She hung on to my arm. :-)

Movies are just part of having an entertaining night.

And–uh–you can talk before and after the movie to get to know one another (and talk about the movie as part of the conversation).


127 Judith February 28, 2014 at 9:09 am

Totally right! I am a girl and I loved when my boyfriend did this during our first date. I am wondering now ig he read this webside… Good luck and follow the steps! :)

128 Michele March 30, 2014 at 3:45 pm

Such a great article. In fact, many of the articles are perfect for my teenage son. The only other thing I shared with my son is that the first date is simply a precursor to a life-long journey about learning how to relate to women. This will lead him eventually learn the kind of woman that he likes vs the ones that are not for him, and ultimately the kind of woman he might like to ultimately marry.

Thank you!

Leave a Comment

Previous post:

Next post:

Site Meter