50 Of The Absolute Worst Dates You Could Possibly Imagine

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I have always thought living in a major city while being single couldn’t be the worst thing in the world. Seemingly, there is an endless supply of eligible bachelors, and you can swipe until your fingers bleed without running out of guys to talk to daily.

However, after years of playing the dating game, I began to notice a pattern.

Never-ending exchanges of, ‘what do you do’s and ‘where are you from’ things before fizzling out into nothing more than a collection of dusty matches on your Tinder shelf. The excitement seemed to be lost by the third or fourth mundane exchange when one of you stopped responding. What was the point of it all if neither of you were going to move any further?

I decided enough was enough. I had wasted too much time having bullshit conversations that went nowhere so if we matched we were hanging out, and it didn’t matter if you were my ideal type or if OkCupid thinks we are only 67 percent compatible. If we flirted long enough to exchange numbers in bar, we were going on a date or having a drink. Basically, as long as I found you attractive and you didn’t ask for nudes, I was willing to give it a shot.

What was the worst that could happen? I get a bunch of free cocktails? I find the love of my life? I get murdered and worn as a suit? The possibilities seemed endless! But for the first time, at least they were exciting.

What started out as an optimistic experiment turned into a slapstick Romantic Comedy, but *spoiler alert*Drew Barrymore didn’t get swept off her feet daily in this film.

I decided to keep notes after each failed attempt, and well, eventually I found myself 50 dates deep with nothing to show forth but this blog so I guess it wasn’t a total loss…

1. Tells me I have beautiful breasts and he would like to paint them “Titanic style.”

2. Has hair system (aka a toupee glued to his head). Complains about women false advertising in their pictures.

3. Has six roommates. Is 35.

4. Asks if I want to see a picture of his dog. Shows me a picture of his penis instead.

5. Suggests we go to a fancy cocktail bar. Drills bartender relentlessly as to why they don’t have High Life.

6. Shows up hammered to date. It’s 7 pm on a Tuesday.

7. Declares himself a “sociopath” but “in a good way.”

8. Profile says 5’11”. Is 5’6″ (in heels). Wines about my recent haircut not being the same as my pictures.

9. Talks about how much I remind him of his ex. “That worthless bitch.”

10. Brings his buddy on date to confirm I am not crazy.

11. Profile picture is a gym selfie. Shows up looking like he ate his former self.

12. Suggests (based on venue) I dress to the 9s. Shows up in (mystery) stained sweatpants.

13. Asks me how I feel about kids because he wants “a solid dozen.”

14. Tells me if I ever want any kind of commitment from him, I would have to have three or foursomes. Girls only.

15. Asks me if I want to “get outta here” aka head back to his place during the appetizer.

16. Broke up with his girlfriend of two years on Tuesday. Felt it was time to get back out there, on Friday.

17. Orders a round of shots. When I explain I work in the morning and can’t do any shots, he does both. Orders two more.

18. Refers to himself in the third person multiple times.

19. Tries to convince me during dinner that humans only need to eat once a day, and I was being gluttonous by having my *gasp* third meal that day.

20. Talks about his summer home and how he can’t wait to take me there. (It’s December.) Ends same conversation with he’s “not looking for anything serious.”

21. Asks me if I keep everything groomed as nice as my eyebrows.

22. Tells the waitress since I have a leather handbag I can afford to cover the bill.

23. Orders dessert to share, tells me I am allowed two bites so I don’t let myself go.

24. Asks me about my family. I mention I have a sister. Asks me if she’s hot. More than once.

25. Flirts with hostess. And waitress. And girls at next table. Claims he is just friendly as he passes out his business card to only females skipping their male company.

26. Kisses me on the cheek each time he gets up to use the bathroom, which is seven times in two hours. Each kiss gets longer.

27. Talks about his love of hunting. Casually mentions how it would be fun if he could hunt people.

28. Continues on about how much his mom loved his ex, and how she would never ever accept me. EVER.

29. Asks me if I want to try out a fancy new Italian restaurant. It was Olive Garden, and I was overdressed.

30. Tells me I look really good naked because he has been undressing me in his mind all night, and he can tell.

31. Puts bar’s salt shaker in his pocket because his has been missing.

32. Suggests we go get matching tattoos because he knows I am the one, ten minutes into our first date.

33. Informs me he scoured my blog but couldn’t find any information on my stance regarding anal. Precedes to ask me my stance.

34. Asks me to cover the bill because he’s saving up for a PlayStation 4.

35. After dinner suggests we go get ice-cream so he can “watch me eat it.”

36. During a good night kiss, pulls away to tell me I am good kisser…just like his girlfriend.

37. Asks me how I feel about recreational drug use. Confirms he smokes “a little meth.”

38. Interrogates me regarding how many men I have slept with because anything more than five for a woman is “disgusting.”

39. Inquiries about what his chances are of seeing “dat ass” later.

40. Leaves the waitress a seven percent tip because “a monkey could do her job.”

41. When I decline the offer to go back to his place, he points out that he paid the tab SO (with a nudge nudge wink wink).

42. Has three tattoos of girls names. All different.

43. Responds to a Tinder message mid conversation (before we even order).

44. Profile says “entrepreneur.” Actually is unemployed.

45. Gets up to order our drinks. Watch him intensely smell a girl’s hair sitting at bar.

46. Uses the phrases “on fleek” and “swag” multiple times in conversation.  Is 33.

47. Takes a phone call for 15 minutes. During dinner. At the table. In a very quiet restaurant.

48. Runs into (male) friend at bar. Introduces date to said friend. Date aggressively interrogates me as to whether or not I had sex with said friend. In front of said friend.

49. Eats French Fries one by one with a fork and knife by slicing them, very slowly, lengthwise.

50. While nervously playing with my ring, it falls to floor. He retrieves it from under table. Licks my leg on the way up. Thought Catalog Logo Mark

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