Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

5 Biggest Dating/Relationship Mistakes I’ve Ever Made

I’m 39 and single.  I’ve never been married, have no kids and have never really lived with a guy, not for any period time.  On these facts alone one might assume a few things:  I’ve dated a lot.  I’ve had quite a few relationships. And that all of those relationships failed.

These would be fair assumptions.

It would also be fair to assume that my behavior occasionally contributed to those breakups.  On a totally random tangent, what’s your favorite breakup song?

So here for your mockery today are the 5 Biggest /Relationship Mistakes I’ve Ever Made.  You’d think there’d be more, but the truth is I make the same mistake over and over.  I’m dumb like that.

1) Fixating on my first impression of a guy, even when there’s significant evidence to show I’m wrong.  I did this with Mr. Potential (Who I described in my first few dates as kind and considerate.  Then when he stopped being kind and considerate and started taking me for granted I still kept saying, “but he’s so kind and considerate”.  I should have realized my first impression was wrong and moved on much quicker.) and I’ve done it many times before.  I’ve wasted the equivalent of years of my life in relationships with men that were completely wrong for me, but I didn’t realize it because I was so fixated on my first impression of them.

2) Putting important thoughts and feelings in emails. This is a big sin and I have no excuse for it.  It’s childish.  Even in the case of a long-distance relationship.  It’s just so much easier for me to say what I’m feeling in writing.  But still, it’s wrong.  I must learn not to do it.  Ever again.

3) Impatience (ok, not so much a mistake as a character flaw that leads me to make mistakes).   I am not the most patient woman on the planet.  That is a huge understatement.  I’m a New Yorker by birth and certainly by temperament.  I make decisions fast and want to act on them just as quickly. And it’s hard for me to adjust to another person’s pace.  My impatience has hurt some of my relationships and I know that.

4) I hold on to grudges. I’m thick skinned and have very liberal views about a lot of things.  I like open relationships and think people need lots of space and free time.  And so I don’t get bothered by a lot of the typical things,  But when someone does upset me, really upset me, I have a hard time letting that go.  Harder than most people, I think.  I hold on to grudges longer than I should. And it makes it harder for men to get back into my good graces.    I’d like to think that I’ve learned my lesson on that.  Only time with tell.

5) I date the wrong men.  Still.  And I have no one to blame for that but myself.  I’m trying to change this.


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12 to “5 Biggest Dating/Relationship Mistakes I’ve Ever Made”


  1. nandoism says:

    I can relate to #1. That’s a tough one because I guess we just want to hold on to the illusion…right? Girl, keep up with these thought-provoking posts. Thanks for making me think.

  2. Devon aka Dru says:

    I think number 1 is the biggest problem for us all. I was just talking to my friend today about my last ex-boyfriend and how because of my impression that he was good and kind in the beginning, I had a very hard time letting go towards the end even after seeing his true colors. On the random note, one of my favorite break up songs is Ben Folds 5 “Song for the Dumped”. It’s angry and funny all at the same time :)

  3. BBboy says:

    Well done Simone! My first though though was that if one dated a lot, wouldn’t they be able to correct, or understand at the very least, #5? I’m assuming that if you are trying to change this, you do have a better understanding about this. Am I correct? Bobbyboy

  4. LPS says:

    It’s harder than you think BBboy! Unfortunately. People gravitate to what they know best. It’s very hard to break the pattern, even when you do try to date “out of your type”. Great entry, Simone! Thank you! We’re all the guilty of those same 5 things at some point in our lives. Even those who hate writing and prefer communicating face-to-face. Everyone has their own character trait where they avoid communicating their thoughts & feelings about the relationship or person.

  5. sfsingleguy says:

    “And that all of those relationships failed.”

    What is your definition of failure?

  6. Singletude: A Positive Blog for Singles says:

    Kudos to you for being so honest with yourself about your own relational patterns! I hope awareness leads to change in this case if that’s what you want.

    Add me to the list of those guilty of 1. Research on first impressions shows that they’re very hard to rub out once formed, so I try to cut myself and everyone else some slack on this.

    I wonder why you say it’s not okay to put important thoughts and feelings in writing? I also find it easier to express myself that way and often do. I always thought it was more important that I communicate rather than that I communicate in a specific mode. At several critical relationship junctures, I remember asking an ex if I could put my feelings in writing because I was having a hard time verbalizing them, and it always worked well.

    I’ll nominate Fiona Apple’s “Sleep to Dream” for favorite break-up song. Anecdote: I was seeing a Nice Guy (on first impression) who suddenly morphed into a First-class Douchebag when I wasn’t looking. When some cracks appeared in Mr. NG’s facade, Fiona Apple’s unforgiving lyrics began to run through my head. Amazingly, as I played with the radio dial in the car, I happened across the song. This was some 10 years since its release, so it wasn’t in heavy rotation at the time. Still, I didn’t believe that Mr. NG was really just going by his alias and was actually FD, so I took him back. When he pulled his final disappearing act, I turned on the radio, once again heard “Sleep to Dream,” and knew for a certainty he “had [his] head in the clouds” and was “not at all what [he] seemed.”

  7. drumdance says:

    My take on email is it’s fine, even great, for positive thoughts like a love letter or even just a note of encouragement, but terrible for anything that might seem negative or ambiguous.

  8. Simone Grant says:

    Wow, I’d never realized how common number 1 was. Nandoism and Devon aka Dru, sorry to hear that you both do it, too. But always happy to hear it. Makes me feel less alone.

    BBboy, It can be hard to override a pattern of behavior that goes back over a couple of decades. Even if you recognize it’s not good for you.

    LPS, thanks for the support and understanding. Good to know that people can relate to these, that I’m not alone out here.

    sfsingleguy, Good question. And, in reality, I misspoke. I don’t think they were all failures. A failed relationship, to me, is one where I didn’t get what I wanted out of it. Where both parties didn’t. Where we tried and failed, And I’ve had a fair number of those. I’ve also had plenty of casual, easy going relationships where everyone got what they wanted.

    Singletude, When I put my thoughts into writing I have a tendency to say to much. To go too far. I don’t hold back. And that can be bad in all sorts of ways.

    drumdance, I’m sure for many people that would be great. And if I could learn to send short little notes of encouragement, I’d think that would be great. But I overstep and that’s dangerous.

  9. Veka says:

    I, too, am guilty of #1, except the opposite. Perfect example is of a guy that I have recently been seeing that I call W. The first time I ever met him, I thought he was a dbag, although attractive. Didn’t see him for months, always called him a dbag when people would talk about him, but then we started hanging out etc. And he’s still a dbag, but I went out with him anyway. I have that problem where I know that he’s a dbag up front but still date them anyway. And my perceptions of him never changed. Oh well. Maybe you and I will both learn one day :)

  10. Simone Grant says:

    -Veka
    Yes, definitely the opposite. Because I get it stuck in my head that my guys are great. If I think someone’s a dbag, I don’t date him in the first place.:-)

  11. VeganD says:

    Wow, amazingly candid – and refreshingly useful – WRITE/RIGHT on!!

  12. Simone Grant says:

    -VeganD
    Welcome to the blog, darling. And thank you. I do my best.