16 Dating Struggles All Overthinkers Face Living In A Major City


1. No one is screened in a big city. Anyone you could possibly go on a date with could be a serial killer, rapist or some sort of crazed lunatic. You miss the cushion of a college screening process.

2. You’d ideally like to know what you’re going to do before the actual date. It’s not formulaic when there’s so much to choose from. You need a game plan and when you don’t know what that plan is IT’S INSANELY STRESSFUL.

3. Meeting someone randomly on the subway sounds romantic but would never actually work for you. You’d be too concerned you’re flirting with a very cute homeless man.

4. Are you supposed to dress for something outside? Will you be walking, or will there be another factor that will effect your shoe choice? These things need to be discussed.

5. What if it actually starts going well and then you learn they live ALL THE WAY ACROSS TOWN? If they live in more than 10 miles away in a city with heavy traffic, that’s basically a long distance relationship.

6. The pool starts to feel too big. Cities hold literally every type of person and it’s hard to find people you’ll actually want to see again. You end up meeting way too many people who have never watched Arrested Development…. How would you ever be able to facilitate a relationship with them?

7. Then the dating pool becomes small and incestuous once you find your niche. Sooner or later you’re going to go on a date with a failed date’s best friend.

8. Picking a place is stressful. Should you pick a spot in your neighborhood? Their neighborhood? Is the halfway point in a ridiculously sketchy part of town? If they told you to pick a restaurant but they may be the one that’s paying, you don’t want to be presumptuous or unnecessarily cheap. Why isn’t acceptable ask right up front about their financial situation?

9. Staying over at someone’s house on a weeknight is a COMMITMENT. Do you bring an overnight bag? Is that assuming too much? What if coming from their apartment lengthens your commute from 30 minutes to an hour? Cue the cost-benefit analysis.

10. Dates on a work night will always send you into hyperventilation mode. You have to commute back to your apartment to get ready after work, which means you can’t get to a date until 8 p.m. at the earliest. Or you can skip going home, but then you have to be ready to go out right after work and hope your hair stays put together for 12 hours.

11. If it’s Tinder, there’s 80 more things you are paranoid about. You need to have a friend on call who will know your exact location just in case your match turns out to be a con artist.

12. What if you have a random overnight guest and they rob you? That happens in movies. Okay, usually it’s because one party is a hooker, but still.


14. A “late drink” can mean literally ANYTHING to city people. Is that 9 o’clock? Is that 11? And if it’s 11 do they realize that’s not going to fly because you need to wake up at 6 a.m. the next morning?

15. You worry your life is becoming too reminiscent of Sex and the City or Girls. You’ve met a sea of people who are interesting to date, but not remotely close to anyone you would want to spend more than a month with.

16. You don’t have an interconnected circle to get intel on your date. In college, if you went out with someone’s friend you could ask the middleman whether the date liked you. In a big city you’re resigned to stalking until you find any mutual friend, and then you toy with the idea of reaching out to someone you vaguely knew 6 years ago to see if they can help you.