Confession–I’ve been in an undefined relationship with the same dude for over a year. The first time I went through Valentine’s Day with him, we had only been seeing each other for about 4 months and it was VERY casual. Due to some outstanding circumstances, and a very bad temper, we did not spend our first Valentine’s Day together, but rather, he ended up ignoring me the whole weekend. #Winning. Fast forward to Valentine’s Day this year, and I’m the SAME situation…with the SAME dude…and I don’t know what to do.

Here are the thoughts that have been going through my mind for the past week. Maybe you can relate?

1. Why is Valentine’s Day more stressful than any other holiday?

2. Should I assume we’re doing something together?




3. I should probably just ask him.

4. It’s not a big deal…

5. So, if he says yes, should I make a reservation somewhere?

6. If so, where should it be?




7. Should it be fancy or casual?

8. I’ll do it. He’s lazy.

9. Fancy it is.

10. Should I tell him I booked a restaurant?

11. LOL, I’ll snap him my confirmation email.

12. He opened it…




13. Is he gonna respond?

14. He’s typing…

15. “You’re nuts, but sounds good.”

16. Alright, semi-dodged a bullet there.

17. However, we’re still two weeks out.




18. Maybe I was too aggressive in making that reservation.

19. He could still cancel.


21. Sweet lord I’m making this a bigger deal than it should be.

22. It’s a fucking Hallmark holiday.




23. Thanks for the stress, card-makers.

24. OK, chill TF out. It’ll be fine.

25. I wonder if I should go get some hot new lingerie?

26. I’ve been working on my bod, I’d like to show it off.

27. Treat. Yo. Self.




28. $100 later and I have an “outfit” that I may or may not wear.

29. ~Think positive thoughts, you asshole.~

30. “He will die if you wear this. It’s hot AF.”

31. Should I send him a pic of the VS stuff?

32. Maybe.

33. NAH, it should be a surprise.




34. Shit, do I need to make my bedroom all romantic?

35. Is that my job or his?

36. Why is all of this on my shoulders?

37. Shouldn’t this be HIS holiday to treat ME?

38. LOL wait, that’s every other holiday.

39. TBH I just want him to commit to the date so I can Instagram it.




40. Damn you, social media, and your enticing ways.

41. This would be a lot easier if I were single.

42. Am I single?

43. We’ve never defined our “relationship.”

44. This is annoying.

45. I quit.




46. Bye, Valentine’s Day.

47. Oh. Wait. He texted me?

48. Aw, he said something cute.

49. It’s happening.




50. For now anyway. We’re still a week out.

51. YAY!

52. I’m actually gonna have someone to celebrate Valentine’s Day with.

53. Maybe……….

54. ~And the cycle will continue until that a-hole is in my bed arms~

55. Fact: I’m crazy.




Emily Bishop is a die-hard Marylander who has recently made the move to Boston. She enjoys telling others all about Maryland, reading books, watching tv/ movies, and being active. Emily can be found saying, "y'all" in almost every conversation. Additionally, she gets a lot of inspiration from her 22 year-old and a 5 year-old brothers (same parents, LOL). She is seriously addicted to Instagram and you can follow her as she adventures through time @ebishop02.

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