(Almost) Free Date Ideas for Any City – By Season.

Yesterday, my friend and I were talking about all of the cool things to do in the summer and (upcoming) Fall/Winter in our cities. As conversations sometimes do, it stretched out to dates and how it’s pretty easy for a guy to please a woman who he’s interested in. Also, please note that I did tell my friend I think women should treat guys, as well. First of all, people get the term “dating” all messed up. Dating is just what it sounds like, going on dates. Whether that be with one person or different people. You date to find what you do (or don’t) like. “In a Relationship” means exclusivity.

Anyway..so we were talking about date nights that were less than $20, because no one ever said you had to spend a lot of money on dates every single time. It’s truly the thought that counts. So, along with the help of a friend, here’s a list of summer (because it’s not over yet) and Fall/Winter date ideas — either free or cost efficient. It’s as easy as googling “What to do (enter date, time frame here) in (enter your city here)”. Thanks to me, you don’t have to do that!

Of course, we’ve seen posts like this before, but not with my commentary. Also, judging by the frustrated women (and men) on my timeline, we haven’t seen these enough.  😉


Festivals – Every city has them throughout every season, especially in reasonably larger cities in the summer.

Movies in the Park – Imagine the largest park in your city filled with people, picnic baskets and blankets. A large screen with movies from Space Jam to Men In Black, and more!

Picnic – Grab a few sandwiches from your local deli, fruit, water bottles and a blanket (clean, preferably lol) and there you go!

Beach Day/Walk along the Beach – I love the beach. It’s absolutely the most calming experience ever, as long as it’s not 90+ degrees. Make a day of it and hang out in the sand, jump in a game of beach volleyball. You can also bring games and get a little competitive 🙃. Not into that? Grab some Icecream and take a walk along the water.

Music Festivals – There’s always free music festivals happening. No, you probably won’t get a free shot at Calvin Harris or Kendrick Lamar, but you can definitely find shows with local artists. For NYC and CHI, check out SummerStage and SummerDance, respectively.

Zoo – Some zoos even have “adult night”. There aren’t that many animals out, but you can still access the zoo and the carousels (well, Lincoln Park Zoo in Chicago).

Baseball Game– Who doesn’t like soaking up the sun with a frozen drink? You can get baseball tickets for as low as $10, you just have to search. Try stubhub!

Farmer’s Market – These markets don’t just have fresh fruits and veggies. Some have food trucks and ready-to-eat food, as well. You may get lucky and see a street performer.


Ice Skating (towards the end of Fall into Winter)

Apple Orchard – After apple picking, go back and make apple pie…or any other Apple centric sweets!

Zoo Lights –Need I say more?


Wine tasting 

Art gallery

Cooking/DIY/Art class (Check Local Grocery Stores/Home Depot/Joann Fabric or Michael’s)

Penny Date – I haven’t done this, but sounds pretty fun. Check it out here.

Chicago Notables:
Okay, even though I live in NYC now, I still have a love affair with Chicago. Here are a couple of notables for just in case you want to splurge a little. Even if you don’t live in the Windy City, there may be something similar where you reside.

Jazzin’ at the Shedd – Jazz music at the Shedd Aquarium every Wednesday during the summer months. I’d recommend going when Detour Jazz Funk performs. They are my personal favorite and are always outside, so you get a view of the water AND skyline while dancing to some great tunes.

Christkindlmarket – This is a German market with different vendors for food, drink, and different trinkets.

So there you have it folks! Just repost this over and over until your secret (or not so secret) MCM/WCW gets it. Again, this is not just a list for guys, ladies you can treat too!

Thank me later.

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