The Best Cheap Date Spots in Every Type of City

The Best Cheap Date Spots in Every Type of City

Jake Holden||9 min read

I went on a date last year that cost $11. Eleven dollars total, for both of us. It was one of the best dates I've ever been on, and the person I went with literally said, "This is the most fun I've had in months."

We went to a taco truck, got four tacos and two Jaritos, sat on a park bench by the river, and talked for three hours while watching ducks be chaotic. That's it. No reservation. No dress code. No sommelier asking if we'd like to start with the wine list. Just tacos and ducks and conversation.

Meanwhile, the week before, I'd spent 180onadinnerdateata"nice"restaurantwherewebothorderedthingswedidntreallywantbecausethemenuwasconfusing,theservicewasslow,andwespentmoretimelookingatourphonesduringtheawkwardwaitsthanactuallytalking.Shetextedmeafterwardsayingshehadanicetime.Itextedbacksayingthesame.Webothknewitwasmediocre.180 on a dinner date at a "nice" restaurant where we both ordered things we didn't really want because the menu was confusing, the service was slow, and we spent more time looking at our phones during the awkward waits than actually talking. She texted me afterward saying she had a nice time. I texted back saying the same. We both knew it was mediocre. 180 for mediocre.

The lesson that took me way too long to learn: the cost of a date has almost zero correlation with how good the date is. What matters is whether the setting facilitates actual connection -- talking, laughing, sharing an experience. And the settings that do that best are often the cheapest ones.

Here are the best cheap date spots, organized by the type of city you're in, because what works in Chicago doesn't always work in Boise.

The Big City (NYC, LA, Chicago, etc.)

Big cities are paradoxically both the most expensive and cheapest places to date. The expensive part is obvious -- everything costs more, and there's immense pressure to go to the "cool" restaurant that just opened and has a three-week waitlist and $18 cocktails.

The cheap part is that big cities have an absurd density of free and nearly-free things to do, and most people never take advantage of them because they're too busy trying to get into the restaurant with the three-week waitlist.

Free museum nights. Almost every major museum in every major city has a free admission night, usually once a week or once a month. The MCA in Chicago does it. MoMA in New York has free Friday evenings. LACMA has free second Tuesdays. A museum date is phenomenal because it gives you things to talk about -- you're walking through exhibits, reacting to art, sharing opinions, and learning how the other person sees the world. It's an instant conversation generator in a way that sitting across a table from someone is not.

Neighborhood walks with a destination. Pick a neighborhood you've never explored. Walk through it. Find the weirdest shop, the best-smelling bakery, the mural that's clearly a local masterpiece. End at a coffee shop or a cheap bar you've never been to. This date costs the price of two coffees and it's infinitely more interesting than the standard dinner-and-drinks playbook because everything you encounter is a surprise. I once found a used bookstore on one of these walks that had a resident cat named Gerald, and my date and I spent twenty minutes petting Gerald while discussing our favorite books. Top five date moment. Cost: $0 plus two cappuccinos.

Comedy shows and open mics. Big cities have comedy clubs that charge 55-15 for weeknight shows, and they have open mics that are free. Some of the performers will be terrible. That's part of the fun -- you and your date get to whisper commentary to each other, which creates an instant conspiratorial bond. Some of the performers will be incredible, and you'll both leave feeling like you discovered something together. Either way, you have something to talk about afterward that isn't "so where did you go to college?"

The park date. I know it sounds basic. I'm telling you, it works. A blanket, a bottle of wine (check your city's laws on this -- some parks allow it, some don't, some have a "don't ask don't tell" policy if you're discreet), some cheese and crackers, and a sunset. Total cost: $20-30. The key is picking the right park and the right time. Golden hour -- that last hour before sunset -- makes everything look cinematic. You look better. They look better. The cheese looks better. It's like a real-life Instagram filter.

The College Town

College towns have a specific energy that's great for cheap dates if you know how to tap into it. Everything is designed for people without money, which means the infrastructure for fun-on-a-budget already exists.

Dollar movie theaters. They're becoming rarer, but college towns tend to hold onto them longer than anywhere else. Second-run movies for $3-5 in a theater that hasn't been renovated since 1987 has a charm that a Dolby Atmos megaplex can't touch. The floors are sticky. The popcorn is fine. The experience is excellent.

Campus events that are open to the public. Lectures, film screenings, art shows, concerts by student ensembles. Most universities host dozens of free events per week, and most of them are open to anyone, not just students. A jazz ensemble concert in a university auditorium is a legitimately great date, it costs nothing, and it makes you look like a person with varied interests even if your primary interest is "things that are free."

The breakfast date. This is underrated everywhere, but especially in college towns, where there's always a legendary diner that serves enormous plates of food for $8. Breakfast dates are low-pressure, naturally time-limited (nobody lingers at breakfast the way they linger at dinner), and cheap. You eat pancakes, you drink coffee, you talk about your plans for the day, and you're both energized instead of food-coma'd and sleepy. I'm a massive advocate for the breakfast date. It's the most underused tool in the dating toolkit.

Game nights. Board game cafes exist in almost every college town. You pay a small cover (510)andgetaccesstohundredsofgames.Thisisadatethatrevealscharacter:howsomeonehandleslosingatSettlersofCatantellsyoumoreaboutthemthanthreedinnersevercould.Competitive?Gracious?Strategic?Soreloser?Youllfindoutovera5-10) and get access to hundreds of games. This is a date that reveals character: how someone handles losing at Settlers of Catan tells you more about them than three dinners ever could. Competitive? Gracious? Strategic? Sore loser? You'll find out over a 5 entry fee and a cup of coffee.

The Suburbs

Suburban dating gets a bad rap because the default assumption is that your only options are chain restaurants and movie theaters. That's not true, but it requires slightly more creativity.

Farmers markets. Most suburbs have a weekend farmers market, and it's a fantastic date. You walk around, sample things, buy some absurdly good local honey or bread, and generally have a pleasant, low-key time. The samples alone can constitute a meal if you're strategic about it. I once ate my way through an entire farmers market on samples and left genuinely full. The vendors either admired my commitment or were annoyed. Hard to tell.

Cooking together. Instead of going out to eat, go grocery shopping together (weirdly fun -- it reveals a lot about a person's food values and impulse-control abilities) and cook something at home. The meal doesn't have to be elaborate. Pasta and a salad. Tacos. Stir fry. The act of making something together is the date. For some meal ideas that are actually achievable, I have a whole dinner party guide that includes recipes simple enough for this purpose.

Hiking or nature walks. Suburbs are usually close to trails, parks, or nature preserves that city-dwellers would kill for. A two-hour hike followed by lunch at a cheap spot is a date that costs almost nothing and involves actual physical activity, which releases endorphins, which make everyone more pleasant to be around. Just make sure the hike difficulty matches the other person's fitness level. Nothing torpedoes a date like one person gasping for air on an "easy" trail while the other cheerfully bounds ahead.

Drive-in movies. They still exist. They're mostly in suburban and rural areas. They're amazing for dates. You sit in your car or set up lawn chairs, you've got snacks and drinks from home (way cheaper than theater prices), and the whole experience has a retro charm that dinner at Applebee's simply cannot compete with.

The Small Town

Small-town dating is a different beast because there are fewer venues, but that limitation is actually a gift. When you can't default to the standard options, you get creative.

The "tourist in your own town" date. Every small town has things that locals never do because they've lived there forever and take them for granted. The historical museum nobody visits. The scenic overlook everyone drives past. The restaurant that's been there for forty years that everyone talks about but nobody's gone to since 2015. Be tourists together. It's surprisingly fun to rediscover a place you think you know.

Backyard or porch hangs. Small towns tend to come with more outdoor space. A fire pit, some camp chairs, and a clear night sky is one of the most romantic date settings available, and it costs the price of firewood. Stars are free. Conversation is free. The occasional awkward silence is actually pleasant when you're staring at a fire instead of staring at each other across a brightly lit restaurant table.

Community events. Small towns have parades, festivals, fish fries, charity bingo nights, and other events that sound quaint until you're actually at one and having a genuinely great time. Small-town bingo is legitimately exciting. The stakes are low (the prize is usually a basket of canned goods), the crowd is enthusiastic, and you and your date will have stories from the evening. "Remember that time we almost won bingo and the 87-year-old woman beat us?" is a better relationship memory than "Remember that time we went to the nice restaurant?"

The Universal Truth

The through line here is simple: the best cheap dates are the ones that create shared experiences and give you something to talk about. A 200dinnerinadarkrestaurantwhereyourebothperforming"sophistication"createsfewermemoriesthana200 dinner in a dark restaurant where you're both performing "sophistication" creates fewer memories than a 10 outing where something unexpected happens.

For more ideas along these lines, I wrote about date nights that don't require a second mortgage, which covers some of the at-home and low-cost options in more detail.

The person across from you -- or next to you on the park bench, or beside you at the taco truck -- doesn't care how much you spent. They care whether they're having fun. Whether you're interesting. Whether the conversation flows. Whether you laugh. Those things don't have a price tag, and no amount of money can guarantee them.

Spend less. Experience more. And always tip the taco truck guy well. He's doing important work.