10 Cheap Date Ideas She’ll Actually Love

by A Manly Guest Contributor on July 6, 2011 · 91 comments

in Dating, Marriage, Relationships & Family

Bonus #11: Impromptu living room dance party.

Editor’s note: This is a guest post from Joe Weber of Dappered.com.

“’Cause I don’t care too… much for money, money can’t buy me love“ – The Beatles

If you’ve decided to take on the challenge of dating women instead of simply hanging out with them, there’s both good news and bad news.

The bad news is that you’re going to have to overcome your nervousness and fear of rejection.

But the good news is that taking women out on dates doesn’t have to be expensive. It simply takes a little more thought.

Too many men make the mistake of believing they can buy their way out of thinking. But creative, cheap dates are often the best kind. They’re more memorable than the standard dinner and a movie, and when a woman sees that you’re thoughtful, she won’t care how much dough you spent on taking her out (if she’s a keeper, that is).

So here are 10 fiscally responsible options for when you’re short on cash but still want to impress her with a terrific date…

1. Wine Tasting

Wineries are sprouting up everywhere this side of Antarctica. Most of these upstarts allow wine tasting for free or for a very small price (and often times, those that charge let you keep the glass.) Go and learn about the different wines, what they pair well with, and keep mental notes on which varietals she enjoys the most. Knowing a woman’s preferred type of wine isn’t as important as knowing her eye color, but it helps. As counter-intuitive as it may feel for those of us who see wasting alcohol as a mortal sin, make sure you use that spit bucket. You’re driving, you need to be responsible, and if you swallow every taste you’re not going to be fit to drive her home. You don’t have to spit every taste, but showcase some restraint. She’ll notice and appreciate it.

2. Hit a Flea Market

Unlike antique shops, flea markets seem geared for the young and not as affluent. The merchandise is almost always more interesting if not downright weird. Same goes for the people in attendance and those who are selling the goods. You can watch people barter, look over pieces of furniture that are probably haunted, and maybe pick up some small gift for your date if something inexpensive catches her eye. If it’s jewelery? Who knows. Maybe it won’t even turn her skin green. (Or it could end up being some awesome treasure). Try and stick to outdoor flea markets that have a good reputation. Not those once in a blue moon indoor sales which charge you an arm and a leg before you even get to lay eyes on what’s for sale.

3. The Sunset Hike + Post Pub Visit

Going for a meandering walk with no real destination can be fun, but hiking to the top of an easy to get to peak to watch the sun go down gives you purpose. Keep it to under 45 minutes. You don’t want to go on some epic journey only to end up stumbling through the dark. Reward yourselves with a beer or glass of wine afterwards at a cozy pub. This works terrific in the fall when you can see all the changing leaves around you.

4. The Photography-Filled Afternoon

File this one under the category of two-birds/one stone. Most of us have relatives in other parts of the country (or world) and you never know what to get them for their birthday or the holidays. Go on a photo hunting expedition in your hometown for the places and scenes that best represent where you live. When you’re all done, pick 12 of the best and hit one of the many websites that allow you to upload photos and create wall calendars. There’s your gift for Grandma and Grandpa who live a few time zones away and would love a reminder of what it looks like where you live.

5. The Bicycle Picnic

Picnics are always at the top of everyone’s list for cheap and romantic dates. But mixing in a leisurely long bike ride can make a nice difference. It’s relaxing, you get to enjoy some scenery on the way, and it’s far more romantic and engaging when compared to fighting through traffic and finding a place to park. Keep the menu simple, know any open container laws that might apply to your eventual picnic destination, and make sure you’ve got a backpack and bike gear rack that can handle your load. Take a bike lock with you. You might end up taking a detour on the way home for ice cream.

6. Take a Historical Walking Tour of Your Town

Almost always free, historical walking tours actually make you stop and appreciate the history that most of us drive by every single day. We’ve got our own point As and point Bs, and most of us rarely spend time focusing on the places in-between. Usually these tours are led by volunteers who can be real characters, and the buildings and their stories are never boring. Both (the guides and history) will provide for plenty of conversation at the cafe or bar afterward. Nostalgia, history, architecture, an appreciation for the past… it’s all wrapped up in one of these on-foot freebies.

7. Cheering on Your Local Roller Derby Girls

For the cost of one cheap seat at most major league games, you and your date could watch one of the hundreds of local roller derby clubs duke it out with a rival. Usually a ticket will let you see a couple of bouts, and the speed and spills are the real deal. It’s something different but still sports related, with just enough adrenaline, which doesn’t involve sweaty guys for once.

8. The Untraditional Movie Night

There are two options here. First, if you’ve just jumped into a relationship, skip the new romantic comedy that just hit the Redbox, and instead go with a classic like Casablanca, To Catch a Thief, or even the goofy-as-all-get-out original Ocean’s 11. Grab some takeout, make a meal, or have some cocktails on hand that line up with the plot or location of your chosen old Hollywood story. Set an upscale mood by dressing up a bit. You don’t want to look like you’re settling in for a night on the couch because you have the flu. Just because you’re at home watching a movie, doesn’t mean you shouldn’t dress up for her.

For those that have been in a relationship for awhile, consider reenacting your first movie date. We all (should) know the first movie we saw with our significant other. Find it for cheap on DVD, grab a wicker type basket from a craft store, dress it up with some tissue paper, and load it up with popcorn, M&Ms, and other movie theater-type snacks. Deliver it to her and ask her over for a movie night. Should cost you less than the arm and a leg you spent on just the popcorn and sodas alone when you two first saw it in the theater.

9. Farmer’s Market in the Morning, Making Dinner Together That Evening

Staying in and making dinner together is as romantic as it gets, but use your dinner date as an excuse to hit your local farmer’s market that morning. Stroll past the different vendors, and eventually you’ll start assembling a pile of fresh local ingredients that you can use that evening. You don’t have to get everything at the market. Maybe just the foundational items for each course–perhaps a couple bunches of kale to saute up with some olive oil and garlic, a couple of local organic chicken breasts that will be plenty easy to stuff, and some berries to pair up with shortcake for dessert. Get creative, then use the middle of the day to find some easy recipes and pick up the rest of the ingredients you’ll need.

10. Monopoly. Loser Buys Dinner or Drinks

Don’t scoff at board games (or cards). They can make for a terrific evening in (if that’s what you’re looking for). Put a friendly couples related wager down on the outcome (dinner, drinks… I’m sure your imagination is wandering to other places). It’ll make the game all the more interesting. Skip Scrabble or Trivial Pursuit. Those can get too mentally competitive. Monopoly has enough chance involved that no one’s feelings will get hurt (yours included) if someone completely dominates the other. And dominate Monopoly you will if you nab those orange properties (it’s true, they’ve done studies). Win, and if the prize includes a night out on her dime? Then this cheap date idea just produced another. Well… for you at least.

What are your favorite cheap date ideas? Share them with us and if we get some good ones, we’ll do another installment.


Joe Weber is the Director and Editor of www.Dappered.com where affordable style is the one and only focus. He believes that living right, living well, and looking good doesn’t mean you should go broke in the process.

{ 91 comments… read them below or add one }

1 Kelly July 6, 2011 at 4:23 pm

As a wine-drinking, photography-loving rollergirl, I completely agree with this post.

2 Rob July 6, 2011 at 4:38 pm

Ha! My babe is a derby girl herself! Also, Settlers of Catan is way more fun than Monopoly.

3 Dan July 6, 2011 at 4:44 pm

I’m going to absolutely veto Monopoly through my powers of anonymous internet commenting.

Board games are great. Card games are great. I think they should be played more often and are a ton of fun.

However, Monopoly when played with one other person is a war of attrition. You’re slowly wearing down one person over a long period of time. What’s the shortest game of Monopoly you’ve ever played? If you said “2 hours or under,” you’re lying. Additionally, Monopoly is a game where you’ll know you’ll lose long before you actually lose. Thus, you’ll end up battling your date and it won’t be fun.

Otherwise, great date suggestions.

4 Mike July 6, 2011 at 5:14 pm

The only way to play monopoly on a date is to shuffle the properties and deal them randomly to each other. Whatever you get, you pay for (no trades) and then start the game. Plenty of chance involved and since you’re both starting close to bankrupt and owning property it shortens the game to about 1 1/2 hours.

5 Phil July 6, 2011 at 5:16 pm

I think Dan has something, there.
Pick a game with a relatively knowable time limit and (like the article said, one with a high enough Luck factor to make it fun for both of you). Monopoly is not one of those (most of the games of it I’ve played sure *feel* like they’re approaching that 70-day record). Settlers of Catan has plenty of Luck involved (stupid dice won’t stop rolling 3′s…) but takes FOREVER, at least with all of my friends.
X hands of poker or chit-drawing games like Zooloretto give you a pretty knowable limit for how long the game will go and are pretty random. Something like “The Game of Life” may even give you a chance to think about your future together (always good for a date).

6 David | Almost Bohemian July 6, 2011 at 5:22 pm

Crazy! Me and my lovely gf do almost all of these things. Actually, this is quite reassuring that we are doing it right! :)

7 Laura July 6, 2011 at 5:33 pm

As a wine-drinking, flea market patrolling rollergirl, I also completely agree with this post. I’d be happy to do any of these things on a date. Though some places are friendlier for bikes than others.

8 Derek July 6, 2011 at 5:34 pm

I’ve had a pleasant time playing games like Munchkin in one-on-one rounds. The game is lighthearted enough that it’s not going to be taken too seriously and still provides for the luck-of-the-draw and fun competition that I think makes or breaks a game.

Otherwise, I can’t come up with other cheap date ideas that are worth mentioning.

9 Ilana July 6, 2011 at 5:50 pm

All good ideas. 1, 3, and 9 are my favorites.

10 Caleb July 6, 2011 at 6:01 pm

monopoly is definantly one of the WORST board game ideas you could have said. if you wanted something a little more “traditional” why not go with “life” or “clue”? as it is, two games mentioned above, settlers of catan and muchkin mare fun, entertaining games than will be over with in an hour or two (munchkin is hilarious btw). besides monopoly, great post!

on another note, I just saw a roller derby and was considering that for a date… good to know im on the right track there.

11 Al July 6, 2011 at 6:37 pm

Another good afternoon / evening idea for the summer is church or ethnic festivals. Pittsburgh is full of them all summer long.

12 Tyler K July 6, 2011 at 6:57 pm

I took my now wife on a shopping trip to find me jeans. She kept complaining that the one’s I had didn’t fit me right. She thoroughly enjoyed watching me model every pair for her. It’s not quite so cheap if buy a couple pairs though.

13 The Duke July 6, 2011 at 7:01 pm

If your girl is nót a ‘ouch i broke my nail’ kinda gal, i would suggest the following (if the opportunity arises) is the following: A classic B&E: Breaking and Entering….

Now don’t be scared…..i did this a couple of times in old buildings awaiting demolition. Be sure to find out if the structure is about to collapse or not, but in Holland (where i live) there’s hardly a chance. It’s a game of dress up (which girls love) with woolen hats, turtlenecks, combat boots and anything black, and the absolute thrill of going where you shouldn’t be, and where no-one has gone in a long time…..Be sure to bring a GOOD flashlight, a couple of candles, and something to drink…..when inside, you will really have tons of fun in doing anything you want to, and if you get caught, there will most likely be only the proverbial ‘slap on the wrist’ by the cops……no danger in that…

This, my friends, is a UNIQUE experience, something someone will never forget….

14 The Duke July 6, 2011 at 7:02 pm

subtract one of the ‘followings’ btw……..

15 Natasha July 6, 2011 at 7:05 pm

This list is pretty good, but I disagree with some of these suggestions.

The bike picnic sounds wonderful (I love exercise and the great outdoors, personally), but unless you own your own bikes (which aren’t cheap if you want good quality ones), you’re going to have to rent some (which can also get costly depending on where you are and how long you rent.)

Not sure about roller derby, either. Again, I personally find this idea to be awesome because it’s so unconventional and I think roller derby is fun and empowering (I loved “Whip It” so much that I briefly entertained the idea of joining a local league, to give you an idea!), not to mention it gives your guy a little eye candy, too, but if you’re taking out a woman who has jealousy or insecurity issues, I’m not sure taking her to a place where cute girls rolling around in skimpy outfits and crowds chugging beer is a good idea. (Then again, if your date is jealous or insecure, maybe you shouldn’t date her…) I guess it just comes down to what both of you like and what type of woman she is?

Also, might I suggest kicking the Monopoly suggestion up a notch by making the loser owe his or her date sexual favors instead? Haha. Maybe that’s just me or something to be saved after you’ve been together for a while…

16 Josh July 6, 2011 at 7:13 pm

For fun two-player games that work way better as “date” games than Monopoly, I like “Sequence” or “Lost Cities.” If you have a little more time to learn a game, you could try “Balloon Cup” or “Carcassonne: Hunters and Gatherers.”

Read about them at Board Game Geek.com or Amazon.

17 Richard Kern July 6, 2011 at 7:18 pm


Borders/Barnes and Nobles ALWAYS have cheapo astronomy books in the bargain bins. Also, if old-school starfinders aren’t your style you can pony up some cash for the StarMap app (as featured on AoM’s article on iPhone Apps for men) or find yourself a free program online and learn the stars. Impress your date with your knowledge of the constellations and the myths that accompany them!

Be sure to bring out a blanket to lay on/wrap up in, some snacks and drinks and a telescope or set of binoculars if it tickles your fancy.

18 Michael-James July 6, 2011 at 7:19 pm

If it’s a double/triple date, I recommend Risk and some decent red wine. Caution: participants must have good senses of humour. When executed correctly, Risk/wine nights can make for very memorable (in a good way) times.
These are all brilliant, I’ve actually done 1, 2, 5, 8, 9, 11 (with great success I might add) before and definitely plan on trying the rest, thanks for the inspiration!
Also, you forgot IKEA! :D

19 thump July 6, 2011 at 7:30 pm

I used to live near a penny arcade filled with old-school games. Nothing better than shared, hearty laughter to start off a great date. Also, when my wife and I first started dating I took her to a pool hall and we played for kisses. If I won, she had to kiss me and if she won, I had to kiss her. Bi-winning.

20 Collegiate Gentleman July 6, 2011 at 7:35 pm

“The Duke,” I second your breaking and entering idea. Many an evening, I’ve snuck into my College’s football stadium with a lady. I haven’t had the opportunity to try other venues, but I can’t wait to try.

21 Desmond July 6, 2011 at 7:36 pm

One thing I’ve always had a lot of fun with is this cheap little pocket sized palm-reading book I picked up at Chapters for $3. That, and tarot cards have made for some very uniquely amusing dates, I’ve found that if she sees the fun even in silly stuff like that (I know I certainly do) then she’s definitely a keeper!

The first summer with my then-girlfriend (now fiancee) we drew up a long list of old movies we wanted to see, and made sure to watch most of them (it was a long list) during that summer. Sometimes at her place, sometimes mine, sometimes we’d play it on a laptop which we could take anywhere, like outside on a field under the stars, or out camping for instance.

Impromptu picnics are also great.

22 Brian July 6, 2011 at 9:01 pm

One great cheap date that I’ve done is build a fire. It works best when it’s getting chilly out. I told her just to dress warm and nothing else. I found a place outside of town beforehand where we could see the stars and brought a blanket. It shows your manly ability to start a fire and it’s always nice to cuddle up by a fire.

23 Camo Rodeo July 6, 2011 at 9:22 pm

I like all of these and have used several as reasons to hang out with friends that I didn’t plan on dating as well.

My favorite is the Roller Derby, but because I know most of the girls in the local league and volunteer and skate with them. I am the captain of the local men’s team. I guess it wouldn’t be much out of my element to go to one but I have enjoyed taking friends that I could explain the game to as it was played. Anyone that hasn’t been needs to go and see the excitement. The men’s games are becoming more popular so maybe you can get to see a guys bout and girls bout for the same ticket.

Watching movies that both people have seen before is fun too, it keeps you from having to be so wrapped up in all the new excitement that you can joke and chat some while the movie is playing.

24 Jupiter Calhoun July 6, 2011 at 9:43 pm

Took an ex-girlfriend to a roller derby once. By the end of it, she was considering trying out for a local team. I couldn’t convince her that she was tough enough. It would have been fun applying Icy Hot to her…ever…so…slowly.

25 Andrew July 6, 2011 at 9:44 pm

Don’t forget the old standby: mini-golf! Chances are even that she’ll do better getting the ball through the windmill than you, which is a great way to break the ice.

26 Karen G July 6, 2011 at 9:47 pm

Wonderful ideas. As a person of the female persuasion I can attest to this simple truth: thoughtfulness is better than money. All women really want is to be thought of as special. Now I like a fancy restaurant, but anyone can make a reservation. Some of the ideas here are much more fun and memorable.

27 blaine July 6, 2011 at 10:01 pm

I’m a college student and like having a girlfriend, so I’m definitely gonna refer to this on date night. haha.

What I normally suggest whenever a friend asks me for a cool date idea is to bring a girl somewhere that reflects what they like most. For example, I love dogs, hiking, music and the city, so depending on the woman I normally bring the girl to see some live street bands and to get some coffee downtown, bring her to a pet shop after lunch, grab a picnic and go on a hike or go find a talented local band playing where tickets cost no more than $5 each. Not only are these cheap (no more than $10), but memorable dates that’ll show the girl a good time. Hope these helped! Good luck men.

28 Colonel July 6, 2011 at 10:04 pm

Man, you guys are spoilsports. Monopoly is a fun game, though time consuming.

29 Nicholas July 6, 2011 at 10:09 pm

Bowling, bike rides and walks have worked well for us, as well as mini-golf and disc golf.

We also used to spend long hours parked in the train yard, reading books and snuggling as trains went rumbling by. Many happy memories. We had once even considered jumping on board a freight train and seeing where we would end up, but I guess now that we’re married and have a kid, we’ll have to pass on that :)

30 James July 7, 2011 at 12:37 am

#3 Sunset Hike was my go to date when I was in Hawaii. One even turned into a sunset and sunrise hiking trip, when we dicided to spend the night under the stars to watch the sunrise.

31 Carl Johnson July 7, 2011 at 6:00 am

Hmm., sounds interesting., but unfortunately, in my country, riding a bicycle only can be done at the night. In the morning, you just can watch the super Traffic!. :D

32 Stephen July 7, 2011 at 7:07 am

@The Duke July 6, 2011 at 7:01 pm

You don’t need to be the “ouch i broke my nail” type to not enjoying breaking into places.

33 Greg July 7, 2011 at 7:29 am

I find it hard to believe anybody does any of these today…

Wine tasting? Cool, try-hard, but cool, however nowhere exists anywhere near me for this.
Flea market – I like this
Sunset hike? Has anybody suggested this for a date and not been laughed at?
Bicycle ride – I’m not 14.
Historical walk of the town – I cringe at even the idea of suggesting this.
Never heard of a roller derby, ever.
8,9,10 are all decent.

34 The Duke July 7, 2011 at 8:34 am

@Stephen July 7, 2011 at 7:07 am

Absolutely right! But if she is, there’s hardly a doubt about it, wouldn’t you say? I’m really not saying that any girl who isn’t afraid of breaking nails will be in to it, just mentioning that if the girl one is dating belongs to the aforementioned persuasion, one would probably have more success actually applying the lyrics of ‘It takes two to tango’.

I do believe that i have neglected the fact that i know nothing about US law and policemen whatsoever, so i would like to ask you all the question: Could my idea be put to use in the US, or will the first trooper to drive by most likely force you to leave at gunpoint?

35 Morris July 7, 2011 at 8:50 am

Visit museums!
Do something meaningful together….
Volunteer to usher at your local community theatre or regional theatre.

Volunteer to help with your community festivals.

Volunteer to help clean up your state parks.

36 Heather July 7, 2011 at 10:27 am

Funnest date I ever had: hiding mini candy bars in a campus building late at night and trying to find them. Cost about $1. SO much fun.

I second blaine’s thought, find what the girl likes to do best. (Of course if you’re dating her you probably both have the same interests…) But i have been set up on blind dates where I kindly told the guy I’m not a sportsy/outdoorsy kind of girl, and he plans something where we go hiking. The inconsideration is kind of a put-off.

37 Mike July 7, 2011 at 11:36 am

If you live west of the Mississippi, Ghost Town tours can be cool, as well. Most are within driving distance from the major urban areas, and some few actually have ruins/graveyards/functioning restaurants. Not sure about other states, but, in Texas, type up the Handbook of Texas Online, search for the key words “ghost town”, you’ll get about 15 pages of former urban centers, latitude & longitude and, sometimes, directions.

38 oliver July 7, 2011 at 12:08 pm

Hey, monopoly, every time i’ve played that people always get upset. If a person playing does not know how to persuade then they will get upset when someone won’t trade with them.

39 Tyler S. July 7, 2011 at 12:22 pm

Wine tasting is great, but if you do it, there is usually a wine trail. Use that to get to your destination if you are going to a winery to do it, and do not go on the highways. Wine trails are there for scenery and it will give you something to talk about over your drinks.
Also, do not go on double dates unless you have to reason…reason being you are always in competition with the other couple. For example, you pour a glass of wine for your girl, then the other girl says to her man, “must be nice.” It just creates unwanted tension whether it is visible or not.

40 Stephanie I. July 7, 2011 at 2:27 pm

In the summer our downtown hosts free concerts in the park as well as movies outdoors…ALL FREE!. Google local events and you may find the same in your neighborhood.

41 Claude July 7, 2011 at 7:48 pm


42 Joe Redgrave July 7, 2011 at 8:19 pm

taking the wife out to moderately priced “favorite place” dinner then going to the Alcohol super store (Total Wine & More) or grocery liquor store and pic out something to drink during netflix/zune rental (X360) evening.

43 Ethan July 8, 2011 at 12:33 am

Good list, but have you never played Monopoly? I play a lot of board games and few are as cut-throat as Monopoly. That game was designed to destroy relationships, not nurture them!

44 Therese Z July 8, 2011 at 12:12 pm

To your local (smaller) college’s concerts, theatre, or athletic events. 1% less professional but who notices after a few seconds? The price is right, you are supporting the community, the students love an audience.

45 jimmy-jam July 8, 2011 at 12:52 pm

I have found women love:

Free movies in a park
Some dance studios offer a “Social” which has free dance lessons before a dance social
Free Opera/Classical concerts
Botanical Gardens

46 Brett Dent July 8, 2011 at 2:18 pm

@The Duke -
At gunpoint?? What do you take us Americans for? I promise we’re not a bunch of gun-totin’ hillbillies – not all of us. But, it is more likely that, while teenagers may just be run off (assuming they’re not vandalizing), adults might get a citation and a fine for tresspassing.

Also, commercial buildings are usually condemned in the US for good reason. Forget about cops – worry more about falling three stories to your death because the floor collapsed under you.

I agree with most others re: Monopoly. I don’t think I’ve ever finished a game. I do like the idea, though, to randomly distribute properties. That could be fun and much quicker. As far as board games go, any good suggestions for two-person games? Most board games I’ve played aren’t much fun without 4 people or more. The article said Scrabble is not so good, but with the proper bending of the rules can be a lot of fun – how many times have you cracked yourself up with a group of tiles you had that were phonetically funny?

47 Bill July 8, 2011 at 5:22 pm

@duke one of my best memories was breaking into the abandoned insane asylum in bloomington illinois. I went with about 10 friends in the middle of the night, it was great fun. Brett is right about the danger of condemed buildings. I am more worried about falling through the floors at old farm houses that I like to tour when on a road trip. I live in chicago, and I would be more afraid of homeless living inside and gangs using it as stash/drug houses, rather than the infastructure. As far as the cops, depends on who you get. Some will have their guns drawn, because they have no idea who you ar, or what situation they are dealing with. You might get a warning, a simple citation, or you could be charged with a felony, as a kid in Indiana is now being charged with, for a senior prank of breaking ito his highschool and puting a sex doll in the bathroom.

P.S. to all, sorry I kind of hijacked this thread. I know it is suppossed to be about cheap/inexpencive dates.

48 The Duke July 8, 2011 at 7:36 pm

@Brett Dent: I truly apologize if i have offended you. I simply recalled reading about a rule/law/SOP that states that a trooper making an arrest should have his weapon drawn. Maybe it differs from state to state. I seem unable to remember that your states seem to differ as much in laws as the different countries in Europe from time to time. I really don’t think of the US as gun-totin’- hillbillies. That’s just i difference in culture/law. Just to relativate this: The Netherlands has one of the highest scores in the world in gun-drawn-to-lethal-shooting-incident ratio. So fact may be (very crudely put) that American troopers ‘always’ have their gun drawn, but Dutch troopers ‘always’ kill when they draw. As i think of it, a matter of culture.

@Bill: Much obliged for the information. I was really just wondering about cultural differences in that department.

@Bill and Brett: Are there truly that many buildings in dangerous disrepair? I wasn’t aware. Buildings here mostly fall in the category: Butt ugly, let’s get rid of it.

49 Rebecca July 10, 2011 at 12:45 am

For two-player games, Battleship is a classic. Lots of card games are good, like rummy or gin rummy. There’s a 2-player version of Blokus, which is a great and not horrificly long game, but also not a ridiculously complicated game either. I think Scrabble and Boggle and Bananagrams are all great word games but not everyone likes word games.

Also, it could be fun to work on a puzzle together, with a glass of wine and music playing. Thrift stores often have puzzles for $1. You could even work the puzzle, write a message on the back, then take it apart again and give it to her as a gift or work on it together with her.

50 tasya July 10, 2011 at 10:22 pm

I don’t like the roller derby idea at all. Think about it. You’re there on a date.

51 Renee July 11, 2011 at 3:15 am

I love these ideas. I’ll add that in DC most of the museums are free so those are free dates, tour the National Archives, the Botanical Garden or The Capitol building- all free. There are tons of festivals here all year. Kayaking on the Potomac is only $14. And if you live near an LL Bean you can learn to Kayak for about $15 or learn to fly fish for $10. There’s a lot to do inexpensively and it gives you a chance to get to know the person.

52 Kat July 11, 2011 at 10:29 am

If more guys planned dates like this, I’d probably date more often!

53 Rone July 11, 2011 at 11:12 am

Excellent suggestions, and a great job of framing the article as always. I second Renee’s suggestion of the museum date, many free museums are maintained by enthusiasts of the subject matter found there and can be a lot more engaging than you might think: a great conversation starter for those first few dates.

I’d like to suggest taking time to make something together. As anyone in a band, acting troupe, or athletic team will tell you, brainstorming, rehearsing, and creating together can be key to the kind of long-lasting friendship that is essential for a long-term romantic relationship.

Short story books, paintings, songs, any way of utilizing your talents together to produce something will not only engage the both of you throughout, it will give you a product by which to remember your time together: possibly even one you could share with others.

54 Maxwell July 11, 2011 at 12:30 pm

I would recommend checking out local museums. If you do a bit a planning, often times you can find discount days. Who doesn’t love to get cultured and spend less money. Also, aquariums are a go to of mine. At night aquariums usually offer half price or discounted tickets. A little bit of planning before hand can save some money

55 Derek Hilleee July 11, 2011 at 9:04 pm

Swell article. I love the articles that keep me from having to think for myself.

56 Lily July 12, 2011 at 1:56 am

Going to a planetarium can also be fun. Some even offer free star gazing outdoors or cheap indoor viewing with storytelling. This trip would be less intimate, but still enjoyable.

Creating a scavenger hunt (nothing drastic or long), further along in the relationship, will provide thinking on both sides (creating and solving) and, depending on the clues, end in getting to know more about the other person while revisiting shared memories. This will also give the person who created the scavenger hunt time to make sure everything is ready for the end of the hunt, say a dinner/movie/surprise/etc.

Another date idea would be to teach each other something. For example, if one person wants to learn how to (roller/ice) skate and the other one knows how to do that. This does require one person wanting to learn something the other one knows how to do, but I’m sure it can be fun even if both don’t know how to do the same thing. Simple equipment is cheap and easy to rent, but if one person knows how to do something, the chances are that that person already has the equipment, at least for him/herself.

57 becki July 12, 2011 at 6:28 am

Let me tell you how much I love the date ideas on this list! My ex-boyfriend did the calendar last year (when he was still my boyfriend,) and it’s one of my very favorite gifts from him. These are date ideas that would make me think about the guy I was doing them with as a “keeper.”

58 Red Bunny July 12, 2011 at 9:56 am

The first date I ever took my wife on was to the zoo. It was great because it’s kind of an un-traditional place to go for a date. A good rule of thumb is to take your date somewhere where she might have fun with her friends. If someone is having fun, they’ll associate that fun with the person they are with. Lots of traditional dates can be boring, like dinner and a movie. What if she doesn’t like the movie? Or what if your dinner conversation becomes dry because you are both nervous and can’t find anything to talk about other than the weather? Those types of dates are disastrous. My suggestions are a zoo, an amusement park, a football game(any sporting event for that matter, just make sure it’s one that SHE likes. If she’s not into football ask what she is into and take her there instead), bowling (don’t knock it until you try it. She’ll appreciate your sense of humor when you suggest the bowling alley and you will both have fun laughing at how terrible you are at bowling), miniature golf, things like that. Avoid quiet, boring areas like art museums or fancy restaraunts. You can try and show her your intellectual side on later dates. Right now, she needs to feel that when she’s with you, she’s not going to be bored to tears.

59 Dawn July 12, 2011 at 11:39 am

Not only are these fun date ideas, they’re precisely what my long-coupled husband (together about eleven years, married for seven) and I tend to do when we want to spend time together. (And let me tell you, moving to a very walkable apartment has given us a lot more time to talk and hold hands like the disgustingly cute couple we are, plus we’re losing a ton of weight.)

We met when I was quite young (so was he, but a little bit older), with little spending money, and put a big emphasis on having an egalitarian relationship, so we rarely had big Dates. We’re both pretty frugal and took up cooking as a hobby in college, since cooking is a basic life-skill you need to engage in all the time, and it may as well be fun.

60 Kels July 12, 2011 at 1:37 pm

I wanna go on all these dates!.. minus monopoly, I would substitute xbox!

61 Roger July 13, 2011 at 1:50 am

Not bad but is there anywhere other than treatment for cirrhosis you can do for a second date?

62 Encarnacion July 13, 2011 at 3:27 am

One Sunday morning my boyfriend took me to a park with a lake, where we just took a slow stroll and enjoyed each others’ company. Half way around we stopped and sat down to read from our favorite book, the Holy Bible, and talked a bit on the ideas presented therein. Then we got up, and continued our stroll. Then about three-quarters of the way around, he made me slow down and stop, set the Bible on the ground, placed his knee on it, and asked me to become his fiancee, which i happily accepted. Guarantee you i loved every bit of it and won’t ever forget it.

63 Dave July 13, 2011 at 12:08 pm

Combine movie night with a simple home-cooked meal. And, if she (or you) live in an apartment with a pool, an evening swim as the sun sets also works. Mine likes hiking, so we hit the trails & do some bird-watching (she’s a bird freak), too.

64 Robert Brown July 13, 2011 at 9:25 pm

Great article. My fiance and I are in a long-distance relationship, so we love dates that get helps us get to know each other better.

The photo on the article is a lot like us-we’re both music freaks (she even has an ultra-rare lucite bass she plays), and we spend a lot of days travelling around Five Points (birmingham represent!) looking through record shops and thrift stores. We’re both into coffee adnw ine, and the area has a lot of homegrown wineries. *in fact,* if you’re in the alabama area, there’s even a wine trail with the state wineries. You get a passport that gets stamped every time you visit, and at the end you get a wine glass with the logos of the wineries laser engraved on it. Maybe there’s something like that around other states?!

65 Sandi July 13, 2011 at 9:32 pm

My hubby (rest his soul) and I never had much disposable income or spare time trying to work for a living and raise kids. One of our best dates was a late, late night candlelight dinner (after the kids went to bed) on the roof of our house. We were remodeling the kitchen, so he picked up picnic-type stuff, a cheap bottle of wine, paper plates, cups & utensils (so I didn’t have to do dishes later) and set up the ladder – all while I was soaking in the tub. When I came out, he took me by the hand, led me out back to the ladder, and offered me a star-filled night for the evening. Now that he’s gone – I remember that date more than any other.

66 Amanda July 14, 2011 at 3:47 am

I great date is blackberry picking, brambles, or just fruit picking when me and my boyfriend were poor we went bramble picking and then made crumble together it was brill!
We also visited galleries and museums which are free, except for special exhibitions.
Secondhand store browsing too, especially the book stores :)

67 Seth July 15, 2011 at 3:17 am

A cheap date for those of you who live in New York or LA would be to get tickets to Saturday Night Live, Late Night, or the Late Show. Being a member of a studio audience is sure to be something she will remember and it is free.

68 Austin July 15, 2011 at 9:02 am

My favorite (and winning) cheap date is a sailing picnic. I have a small sailing dinghy – just big enough for two and an old-fashioned hamper – and live near the lakes. It’s perfect for the right girl (outdoorsy, adventurous and romantic). I can handle the dinghy on my own or she can crew. To sail you need to be very sychronized and in tune and it’s also a thrilling emotional experience so by the time we get to the picnic spot all the right chemicals in the brain are doing all the right things. It’s impossible not to arrive without a broad smile and a sense of invigoration. The favorite destination has to be an island in the lake. You can’t help but feel like Adam and Eve before the fall in your own private Garden of Eden. Two words of advice for anyone thinking of doing this: it’s cheap (if you already have the boat!) but does require good planning. So, make sure you really know how to sail (qualify via an accredited course and get some experience) or less than comedic disasters could well ensue; check the weather and sailing conditions and have a back up plan if things change; sail out to the island on your own beforehand and choose the best picnic spot in advance (if you can and the place is suitable, leave the picnic and champagne waiting) and finally keep a track of the time and changing conditions. That said, with planning, I’ve never had anything untoward happen. It’s a great one.

69 Malachi July 16, 2011 at 12:54 am

My personal favorite is a picnic and a movie on the beach. I have done this date several times and it still remains our favorite…
Find a beach where there is a ledge that overlooks the sand and water. Bring a large blanket and eat your picnic on it while the sun is going down. When the sun has set, the other inhabitants of the beach start to leave which is the perfect time to set up for your movie…
Break out your 2 beach chairs and your mini “table” set your laptop (with fully charged battery) out and pop in a good movie. by the time you get the movie started, your date should start to get cold which will cause her to snuggle up close. Lay your blanket over the two of you and enjoy the show!!!

70 Loren J July 17, 2011 at 12:33 pm

These are all wonderful ideas. As a young man who is trying to adopt a debt-free lifestyle, I am always on the lookout for ways to spend quality time with my fiancée without breaking the bank. One of our favorite activities is spending a morning going to local garage sales. We have met some interesting people at garage sales, and we always come home with a car full of goodies that we’ve bought for next to nothing. I’ve even made some extra money selling some of our garage sale finds on Amazon or eBay.

71 SheepLute July 19, 2011 at 11:42 pm

I’m “minor”, so I can’t (legally) get wine. But I’ve found that what is our favorite is playing classic board games like checkers, and card games like poker, with shows like Ghost Whisperer, Criminal Minds, and Without a Trace in the background. It’s very fun, and overprotective parents don’t think that you’re doing anything they don’t let you do, if you’re at that age where you and your date’s parents monitor your every move.

72 SheepLute July 19, 2011 at 11:48 pm

Movies are expensive these days… Harry Potter cost me 26 dollars. No snacks or drinks.

73 Bruce July 21, 2011 at 6:48 pm

Cow tipping?

74 Robert July 23, 2011 at 1:30 pm

There in nothing more lovelier yet inexpensive than a chat on the park during sunset.

75 Allan October 8, 2012 at 3:12 pm

I gotta frown a bit about most of these ideas, though a couple are good. In my case, it’s because my wife doesn’t much fit the traditional role.

We BOTH hate wine, doesn’t matter what kind, so that knocks two or three off the list, and she avoids drinking almost altogether. She can’t ride a bike (yes, we’ve tried) and she gets really serious and MEAN when she plays board games! :s

Beating her at Monopoly (or losing on purpose) might earn a night in the doghouse, so to speak.

76 Monica October 22, 2012 at 6:14 pm

Ah, generally good ideas, but a couple caveats to some of them.

I wouldn’t do the roller derby on a first date unless you’re quite certain the girl you’re with likes that sort of thing. I’m a pretty easy-going, pretty secure gal, but it might cause a twinge to be spectating some BAMF ladies with great bodies and tats with some new guy I’m trying to impress. Maybe once we’ve been going out a while, we can joke about the gams on Girl#37, but he hasn’t really earned this right off the bat.

I love Farmer’s Markets and love the idea of cooking together, but I think this one is a little ambitious if you’re new to each other. It doesn’t take a whole afternoon to look up recipes together, which means either the momentum is going to flag, or you’ll part ways for a bit, and parting ways gives both sides a chance to self-scrutinize/overthink dinner plans. Better to combine the FM with the picnic/bike ride. You can usually pick up bread, good charcuterie, fruit, and wine all at the FM.

77 Jory October 25, 2012 at 4:23 pm

A few other cheap date ideas that I have thought of and/or used:

Call up a local Homebrew store, see if they offer free classes. Learning to make homemade hard cider or creating your own root beer or ginger beer together can be a lot of fun.

Libraries often have passes to local museums, zoos, or Japanese gardens. Check out the one day passes and get into the places for free.

Sky lantern’s (if you are too manly to have seen “Tangled” assume she has.) Can pick them up relatively cheap on thinkgeek.com. Find a wide open outdoor space. Write things on them, (like messages in a bottle), light them and set them off together.

78 Rooster October 31, 2012 at 5:56 pm

I’d say B&E into an old abandoned building for a first date screams “please farm my organs out to those in need.” That might be something you do after a few dates.

79 Tyler November 16, 2012 at 9:51 am

The mention of Monopoly sparked some ideas for other games you could use. However, you might want to make sure she likes them before you try them.

-Video games. I could see these being a hit if you’re both into them. When you pick a game, I’d opt for something with a little more co-op play (Portal 2 comes to mind) as opposed to a more competitive multiplayer game like Call of Duty or Halo.

-If you’re both really nerdy (like me), Magic seems like a different take on the classic board/card game night. It has the right mix of strategy and luck, especially if you know what you’re doing. But I want to emphasize: make sure she likes it before you make this your plan. I’ve heard of girls practically running away at the mention of the game.

80 Amy November 24, 2012 at 2:52 pm

Great article. I think the Roller Derby *can* be a good idea for some couples, but if you are easily distracted by (other) pretty women, or if your date is feeling insecure (and ladies, admit it–there are some times when even the most confident of us get a little jealous around other women), then seriously consider doing something else.

Also wanted to mention that if the location/activity is a surprise, you should provide appropriate supplies yourself (such as bringing a jacket or blanket for her if you’re going to be outside in cool weather), and/or at least give her a hint about how to dress!

My husband usually does great on date nights, and once he “surprised” me with a Spring hike in the woods in the moonlight… but I was wearing strappy sandals. Could have been a great date, if I hadn’t been so preoccupied with trying not to get poked in the side of the foot with sharp stones and sticks, and trying to trudge up steep hills and even through a (pretty, but very cold) stream in the dim light, in those slippery shoes. Live and learn!

81 Kit November 25, 2012 at 1:42 am

my husband and I made our own customized pizzas together that’s a lot of fun and we like to go to free open mic nights and see the local talent and sometimes we drive down a road we’ve never been through before to see what’s there. Also our local humane society allows you to walk and play with their dogs for the day for free. You should always look at your community calendar there is quite a lot of free events that happen at least around here.

82 Michael April 18, 2013 at 1:41 am

I’m a country boy so what we like to do is hop on an atv and drive like he’ll off road get both of y’all covered in dirt nd stop at a cliff side during sunset nd watch it set then watch the stars and talk over some beers and then take a shower (together or not) That’s our idea of a great inexpensive date

83 Jazzy June 13, 2013 at 11:41 pm

As a Ref for roller derby. They can make great dates, and you can meet great people.

In fact, i met my future wife at roller derby. I helped her train as a ref and then as a derby girl

84 Christine July 6, 2013 at 9:43 am

AWESOME list! Just to add- many places have indie run movie theaters- you might hit a big screen rerun of a Hitchcock film, or another oldie but goodie. Ours here in Dayton has a cocktail bar, so you can get drinks and a show for less than boring big movie and popcorn.

85 ed. July 6, 2013 at 1:08 pm

#3 for sure. Except don’t tell her you packed dinner with a bottle of wine. Sun goes down. Stars come out. Headlamp and a nice hike back. Perfect. Don’t forget to open the door for the lady.

86 Brian July 6, 2013 at 1:46 pm

So you hike some summit to watch the sun go down and get back to where you started from, how?

87 Willy July 6, 2013 at 2:44 pm

I’m an artist blacksmith with a cozy, well decorated smithy, it is a magnet for the ladies. Many (most) invite themselves on “play dates” where I coach them in the skills. To make these dates interesting we will collaborate on a project , we both have a hand in something she can take home at the end. For long term relationships plan a large or complex project that will be created over a number of dates. We go to art galleries for inspiration, flea markets for fun things to incorporate in our project, this has led to some strong long term relationships. Never let them come to just hang out, or just to watch, when they are on a date with me it has to be a participatory date, no slackers! After working hard we retire to my deck for cool drinks and conversation… with my wife of 40+ years. She taught me how to treat a woman on a date.

88 Ryk Iytean July 6, 2013 at 3:29 pm

The wife & I go to flea markets & yard sales quite often; & here in western PA there is a “free admission” amusement park that dates back to 1892.
It is called Conneaut Lake Park & is in the process of being restored. I took my wife there on a Date yesterday & we had a really good time. Probably spent less than $50.00 including gas.
Rides are $2.00 for adults rides, $1.00 for the kids rides, & $3.00 for the roller coaster.
Paid more for gas than anything else :)

89 Zander Keig October 24, 2013 at 8:23 am

My wife and i have gone on a unique date each week since our first date in September 2002, That’s over 550 dates and climbing!!

We never repeat a date, as a way to introduce intentionality and novelty into our relationship.

Each week we venture out into the world to discover new cafes, neighborhoods, events and people.

I am attempting to capture our fun through the blog Totally Awesome Dates. Loading 550+ will take a while. .. but i welcome the challenge.


90 Mickey Romon December 8, 2013 at 2:06 am

Got my first letter yesterday! Loved it. I feel like I am a element of something great that is certainly just starting to materialize. Feeling a strange sensation of community around it all. Maybe you are on to something here! Who would have ever thought that people today would actually print out words on paper just to have it sent through the mail to another person’s mailbox. Next thing you know, peoe will be growing their own food and walking or riding bikes everywhere. It’ll never ever do the job, damn progress.

91 Caleb S. April 8, 2014 at 8:29 pm

Would going out to dinner and then finding a nice place to dance be a good idea? Also Monopoly is not a good idea it takes far to long and is to competitive for a date.

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