19 Moments When I (Coulda/Shoulda) Realized a Relationship Was Doomed

Hindsight is 20/20 goes the cliché. When looking back on dates, it’s often easy to see the moment you coulda realized it was never going anywhere. In some cases when you shoulda realized it but infatuation kept you hoping. Then there are the times when you realize right then and there that the relationship is doomed. Woulda and actually did realize!


Here is a collection of my coulda-shoulda-wouldas from six years of dating in New York City. Yep, these all actually happened to me!


1 When wandering around The Strand bookstore he looked bored and “Didn’t they make that into a movie?” was his only comment about any book.

2 When he left me standing in the rain, finally showing up 40 minutes late for a date.

3 When he showed up at my job to say hello, I told my co-workers he was “a friend” because I was embarrassed to say he was “the guy I’m dating”.

4 When on the third date he still had made no move. So I made one, simultaneously kissing him and feeling annoyed by his lack of initiative.

5 When he felt up my butt in the middle of Washington Square Park on a first date.

6 When he started choosing to spend way more time with his female best friend than with me.

When he picked me up in a Goodwill.

[photo credit: Matt Harvey]


8 When he told me about the girls he’d also been seeing before he decided he liked me best (i.e. I was the one who would put up with his bullshit).

9 When he made it crystal clear he didn’t want a girlfriend no matter how fantastic/adorable/sexy/smart/sweet (and deluded) I was.

11 When lying in bed one morning he let the sentence slip, “I think you love me more than I love you.”

12 When he got messy drunk after 2 weeks of dating and slurred “I love you”.

13 When I showed up to tell him I loved him and found him tripping on acid.

14 When I had a stress-induced panic attack that left me vomiting on the side of the road, instead of comforting me, he backed away from my retching body.

Woulda (and actually did!)

15 When he disappeared for a week and then called me to say he’d checked himself into a mental hospital.

16 When he tried to find wiggle room in “no glove, no love” and didn’t understand the rhyme is iron clad until the relationship is serious and there’s been serious discussion.

17 When he actually said, “I’ll get married when I’m at least 40. My wife won’t be younger than 24, but not older than 29,” and there was no indication that he was joking.

18 When he called me at 2PM on a Sunday looking for booty.

19 When on a late night subway ride he said to me, “In this lighting I can see all the little whiskers on your face.”


What’s a moment you shoulda (coulda or woulda) realized a relationship was doomed?  I wanna know! Share in the comments or on Facebook or Twitter– if I get enough, maybe I’ll combine them into another post like this!

About New York Cliche

NYC lifestyle blog by Mary Lane. Events, adventures, epic mistakes, dating, life, humor. A 20-something trying to make it (and make out) in the city of dreams.

12 thoughts on “19 Moments When I (Coulda/Shoulda) Realized a Relationship Was Doomed

  1. Love the post. It is so very true. My woulda and actually did moment would be when I walked in to Victoria Secret and the guy I was dating, who was also my neighbor, was there with his girlfriend from his hometown. He failed to tell me he had a girlfriend so I failed to answer any of his calls/texts after that.

    1. oh AWKWARD! especially in VS, yikes! good thing though, or who knows how long it would have taken you to find out!

    1. nope, nope! I know American Horror Story is making bearded ladies cool but it wasn’t cute at all. I could see how maybe it could be, but the way he said it was not cute at all

  2. You are fucking awesome!! Lol alright let me start from the beginning. I was curious as to what’s on the internet about the comedy ticket dudes in Times Square because I see them constantly (started working in midtown couple months ago) and I stumbled upon a gem called the “safa boy series”. Luckily for me it was 5am and reading this wonderful story gave me just the excuse I was looking for to stay up until 9am and just go to work on no sleep (7:51am as I’m typing this). I’m probably gonna get fired today because I will be going through all your posts. Again you’re awesome and you just gained a follower… Oh and for the record us men do love being called assholes.

    1. This comment made my day! Thanks, man, glad you enjoyed reading. If you do indeed get fired on account of my blog, I’ll buy you a commiseratory adult beverage.

    1. ahahaha meme win!
      and I gotta say, curiosity is making me wish you weren’t posting anonymously 🙂

  3. Omg, I love this… I’ve had more than my fair share, but one comes to mind that was a bit too recent… ex-boyfriend, after declaring his love for me over the years (while simultaneously drinking w/ the boys) and with full knowledge of my married status, then further messes with my head the next day when I say, “So, can we talk about this?” and he replies, “On Monday… have a weekend away planned with [then current girlfriend].” Wanted to slam the phone down is his ever-so-delicate ears, but not very effective when you’re texting…. 😉
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