17 Struggles Of Dating In The City

Katherine Ripley Katherine Ripley

17 Struggles Of Dating In The City


So you’re single. You’re back on the market. You’re on OkCupid or Plenty of Fish or Match (God knows how you can afford that but you do you). You’re on a quest to find your true love, but we all know what a hilarious endeavor dating can be. Here are the struggles you’ll probably encounter as a New Yorker playing the fields:


1. You can barely afford dinner for yourself, so how are you supposed to afford dinner for 2?

2. When you get to the restaurant you realize that the cheapest beer is 10 dollars.


3. You and your date live in different boroughs—now you have to negotiate where to meet.

4. You and your date live in different boroughs—that is a looooong walk of shame.

5. Your date doesn’t even live in New York—they’re just visiting for the weekend.

6. Wait…is that your boss on OkCupid?

mulan pouring tea

7. The bar where your date wants to meet is in a sketchy ass part of town and you don’t realize it until you get there.

8. You get stood up in the sketchy ass part of town and people assume you’re a drug dealer because you’re sitting there by yourself checking your watch.

9. Your soulmate is actually the person you made out with 2 years ago at that Halloween party and no one will ever measure up to them.

10. A date doesn’t go well and then you just happen to be taking the same subway home…awkward.

awkward subway gif

11. You actually want to go on a second date but next week the person is off on a three week business trip to San Francisco.

12. This city has 8 million people but somehow you still run into all the dates you didn’t like.

13. You spend an hour on your outfit and then your date shows up in jeans and a ratty T-shirt.

are you kidding me

14. Your date works in the financial district and shows up wearing a stuffy looking suit.

15. Wait…is that your ex on OkCupid?

16. You and your date both share a room with a roommate because rent in this city is ridiculous.

17. Who are you kidding? You don’t have time to date. But you do it anyway because you’re tired of third wheeling and sleeping alone.

crying under desk

Tags: Funny
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