10 Super-Easy DIY Date Ideas Under $20

By | Monday, June 20, 2016


I was weak with laughter and gratitude last week as I read through Rebecca’s post on cheap things to do with your date in a bunch of different cities. As a young, single gal caught in the forever-struggle of wanting to be “on-fleek” while also having a sometimes single-digit bank account, this was the answer to my prayers. Except for one tiny thing: I don’t live in a big city. I live near a big city, but I go there as little as possible. (New York is a pricey $30 train ride away from my quiet Connecticut suburb, making it financially inaccessible to me most of the time.)

The same day that post went live, I went on a date. It was a really wonderful date, but, as dates tend to be, it was also hella expensive (in my opinion). He paid, (Blessings aplenty! If you read this, my lovely date, thank you much for all of the pizza and alcohol!) which I totally appreciated, but I still went home feeling guilty for even having him, this man I hardly knew, spending that money on me. (Please refer to recent post on me having no idea what it is like to be treated to anything by men.)

The next day, I realized I needed to come up with some cheap (so I could afford to pay) or free date options for any subsequent dates I’d have with him, or anyone in the future. Bigger cities tend to offer many free or otherwise pretty cheap activities, but it is more of a task to find something to do in a quiet, less-densely populated CT town that doesn’t require expensive travel or pricey entrance fees. I made it my mission to create a list of all the fun things I can do this summer with my ~special~ dates that don’t involve $12 cocktails or expensive train tickets into the big city.


1. Dog-walking date
My puppy Lilo is my actual wingman. I’m 100% positive that every date I’ve gone on in the past few months was only made possible because her cute little mug is my Tinder profile picture. When I realized that it is absolutely free to tell the fellas to meet me at our favorite walking trail for some puppy love, it became my go-to free date idea. All you need is a cute dog. (Or an ugly dog. They’re really all good.)


2. Going hiking/exploring/being careful-as-fuck in random swimming holes
I grew up in a beach town, but the parking sticker you needed to go to the lake or beach was so pricey that my pals and I took to doing the ~rebellious~ thing and entering the lake from behind, jumping into the cascades and swimming in the river in the woods behind it. We’re lucky we didn’t ever die, or even almost die pulling that crap as kids. But now that I’m a grown-up, I love to (once in a while) rekindle my teenage love of illegally jumping off cliffs. If I want to show my date my insane side, I bring him to the cascades and tell him to hold my stuff while I jump in. (I haven’t been on many second dates.) But hey, at least it was free!


3. Hitting up free concerts
Basically every town in Fairfield County has some sort of summer concert series on the town green. Because of this, I assume that this exists everywhere. (Does it? Please tell.) It isn’t ever exactly a band I’ve been dying to see, but it is always a fun place to drink cheap wine in public, listen to music, and enjoy a warm summer evening for free.


4. Cooking
A classic date night for me is going all out on some super unique Pinterest recipe – and making my guy help out. A memory that I will always hold dear is of a past man-friend setting the table up with candles and picking flowers from my garden to set in the middle, while I cooked up some spicy Thai recipe that didn’t come out at all how I planned. It only costs a bit if you need a special ingredient. Other than that, a home cooked meal is key to a free, quiet evening in.


5. Baking competitions
Maybe I’ve just watched Cupcake Wars too many times, but I think one of the most brilliant date ideas I’ve ever had was to have my boyfriend and I both bake our family’s secret brownie recipes side-by-side and see which one came out more delicious. (I obviously won. Thanks Nana!)


6. Visiting local wineries/Vineyards
This is dependent of course on the area you’re in, but in CT and a lot of surrounding New England states, the vineyards are aplenty. It costs a little bit to buy a bottle or two of their wine, but in exchange you get to bring your own food (i.e. cheap as heck snacks/homemade sandwiches) and enjoy the bootiful scenery. Win-win + wine.


7. Drive-In Movies
Another decidedly un-city-ish activity. My state boasts a few drive-in theaters, and a quick Google search is all it takes to find out if yours does too. It is usually really cheap to get in, no more than $10 a ticket, and totally worth it because you can bring your own snacks and drinks instead of paying $8 for a movie theater bottle of water.


8. Perusing a used bookstore
My ex was an all-around waste of space on planet earth, but he brought one amazing place to my life and that is the Book Barn; an enormous, partly outdoor used book store about an hour away from where we lived in southern CT. The most expensive part of the journey was the gas to get there, but we made a day of it, packed a cheap homemade lunch, and walked around looking at all the bizarre old books together for hours. We rarely bought anything, but when we did it never cost more than a dollar or two per book. Used bookstores are pretty much everywhere, and poring through old books with a cup of crappy coffee is the perfect first (or second, or third, or millionth) date. Pro-tip for students: if you do this at the beginning of the semester, you may be able to find a $200 textbook you need for under five bucks. This happened to me last year and it was the best day of my college career.


9. Going to the library
Similar reasons to idea #7, but an old flame and I used to walk to the library together after work every day in the summer. We would sit there for hours looking through atlases and travel books, planning imaginary itineraries for imaginary future trips together. After that, we’d often check out a few of the books, go to the café across the street for a coffee, and sit outside reading them on the benches for a while. It was super lame, but also super cheap, and so much fun every time.


10. Having a backyard bonfire/campout/stargazing session of any kind
My house is on a pretty big lot, so we have ample backyard space for this kind of deal. Many summer hangouts and get-togethers I’ve thrown have ended in tents being pitched in my huge yard, and a bunch of us sitting around the campfire making s’mores. The most expensive part of this is buying chocolate, because Hershey’s needs to get their shit together. An alternative to this if you don’t have the means to create a fire pit in your yard is to lay out a few blankets, sip your choice alcoholic beverage, and kiss in the d-a-r-k dark while pretending to give a shit about constellations


Mary is the summer Media Fellow at The Financial Diet. Send her your summer intern stories (your lessons, failures, triumphs and good advice) at

Image via Pixabay

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