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

Coulda, Woulda, Shoulda(?)

It might be hard for people who don’t live here to imagine this, but New Yorkers bump into people they know all of the time.  Sure, it’s a BIG city.  But it’s also just a collection of neighborhoods.

This morning, as I was out fetching milk (for my coffee), I bumped into a guy I went out with a few times.  Or rather, I saw him from across the street and moved quickly so that he wouldn’t see me.  I just wasn’t in the mood to talk (pre coffee and all).

And then I got home and had my coffee and started to think about how the story of me and him (there was never an “us”) is a pretty great example of how really is everything.  He and I met online.  He approached me and we moved pretty fast (lots of emails, phone calls, etc).  My first impression of him was that he was gorgeous and perhaps a bit too pretty for my taste (I’m really not into the pretty boys, for lots of reasons) but also pretty damn smart and successful.  And we seemed to have the exact same taste in just about everything.  Seriously – music, art, travel, theater, how we like to spend our free time.  It was the first time I’ve ever met someone who seemed to like exactly what I liked.   And that was kinda neat.

Anyway, our first date was coffee at an outdoor cafe on a beautiful sunny afternoon.  It went well, but it was “off”.  As much as we had to talk about, and as objectively as I knew he was, I wasn’t all that attracted to him and I got the sense that he wasn’t all that attracted to me.  The just wasn’t there.  But at the end of the date he asked if he could see me again and I couldn’t think of a good reason to say no (hanging with him was fun and easy).   He emailed the next day and we made plans to get dinner at one of the better restaurants in my/our neighborhood (oh, yeah, and he lives near me).

Sometime in between the first date and the second date I met the man that would become my last serious boyfriend (aka, the evil ex-boyfriend, aka M).  And he and I had 2 dates, 2 days in a row.  And I knew by the end of date 2 that I wasn’t interested in any other men.  But I kept the date (it was the day after my 2nd date with M).  And it was great.  We laughed a lot and had a great conversation and, honestly, if I hadn’t just met M it might have been the start of something.  Might have…

Within days, me and M were in full relationship mode.  I was meeting his friends and visiting him at work.  And when this guy emailed about a 3rd date, I sent him a reply telling him how much I enjoyed meeting him and that I really meant that but that I’d met a guy – a boyfriend.  And he replied with best wishes.

Jump ahead to months after M and I split up.  I reactivated my online dating account.  One of the first people I hear from is this guy.  He sent me an email to my personal account and we started chatting again and made plans pretty much right away to meet for drinks at a local bar.  And it was great.  He was the perfect person to go on my first date post break up with.  He made it so easy,   And suddenly, I started to think that maybe there could be some chemistry hiding there.

The next morning he emailed, inviting me over to his place for a home cooked meal later that week.  Now, as I’ve mentioned before, when a guy invites me over to his place I consider it code for “I’d like to see you ”.  I accepted the invitation, but honestly, I was stressed as hell about it.  He and I had only seen each other once, recently.  The other 2 dates were pre break-up/relationship with someone who, truth-be-told, I wasn’t 100% over.  I felt rushed.  But I thought he was a great guy and I wanted to see how things worked out with us.  I wanted there to be an us.

Then, the morning of the date, I got an email from him cancelling.  He’d met someone else.  He was sorry, blah blah blah (all the things I said to him) but he wasn’t the kind of guy to juggle women.  And that was a year and half ago and he hasn’t yet returned to online dating.  At least, none of the sites I use.

So when I saw him this morning, me looking like something a cat just spit up, I avoided him.  For no good reason other than that I think of him as someone who I could’ve maybe had a relationship with if things worked out differently.  Maybe I should’ve picked him over M, way back when.  Most women would have (better looking, more accomplished…).  But I went with chemistry.

Or maybe everything is exactly the way it’s supposed to be.  Yeah, that’s probably it.  And I probably need another cup of coffee.


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10 to “Coulda, Woulda, Shoulda(?)”


  1. singlegirlie says:

    What a bitch, that chemistry. I always go with chemistry, too. Whether it’s a good strategy, I really don’t know. What I do know is that I’ve tried to make things work in situations where there’s little chemistry (but the guy is great in theory, so to speak), and I usually wind up hating the guy. It’s not even his fault. I try to give it a chance, thinking, he’s nice, maybe chemistry will develop, and it just never happens. I should say it hasn’t happened with me personally. I’ve heard tales of it happening, in fact many good friends of mine weren’t terribly attracted to their husbands at first and now they’re happily married with kids. And I do mean happily.

    I don’t blame you for going with chemistry. If you hadn’t, I’m sure you’d be saying “shoulda, coulda” about the other guy. Chemistry’s too hard to argue with… it’s no use!

  2. joliefatale says:

    I think you just need that cup of coffee no need to live in the past and the shoulda woulda’s … maybe you can send him an email.. saying that you thought you saw him this morning… emailing to see how he was.. no telling. He may be single and the chemistry might be there.. you know what they say .. “3rd times a charm” or is is “3 strikes your out” either way .. no harm :)

  3. babygirl Karma says:

    I’ve questioned myself many times before , the same way you are with this guy. And there’s never a good way to find out what coulda, woulda, shoulda happened if things /decisions were made differently.

    When I start looking back on things and start thinking(sometimes over thinking ), I just tell myself, ” whatever happens, happens…whatever shouldn’t.. doesn’t”. For whatever reason, it just helps me let go and move on….even when I don’t have the perfect closure on things.

    So I think if you where in the same situation, you might probably have made the same decision again….

  4. nikapika says:

    oooh chemistry! I know exactly what you’re talking about, I always chose chemistry above the reasoning and although I sometimes wished I didnt, it turned out to be a great decion in the end :) love you blog btw!

  5. Anonymous says:

    IMHO chemistry isn’t everything. But it’s something. A big something.
    Stop looking back.

  6. Simone Grant says:

    -singlegirlie
    You and I are very similar on this. I’ve tried to go against chemistry in the past and it REALLY didn’t work. But I have friends who say they weren’t attracted to their husbands at first but… *sigh* I wish someone could tell me the “right” answer.
    -joliefatale
    First, welcome to the blog. I hope we’ll be seeing more of you around here. I thought of sending him an email. What I did, instead, was check for him online. If he was on the dating site I’d send him a message in a minute. But he’s not. I don’t want to be sending emails to a guy with a girlfriend.
    -babygirl Karma
    You’re right, of course. I like to believe that things work out the way they should. However, maybe I am supposed to learn from this. Perhaps the lesson is that I let things move too quickly with M and that I should’ve continued to date them both for a while? Maybe things would have worked out the same. But maybe they wouldn’t have.
    -Anonymous
    Point taken.

  7. Simone Grant says:

    -nikapika
    Oops, I didn’t mean to ignore you darling. First – WELCOME. I hope to be seeing more of you. Chemistry IS pretty damn powerful.

  8. Singletude says:

    Attraction is a complicated thing. I think some people have a wider range of attraction than others, and some people have the capacity to develop attraction, whereas for others, it needs to be there upfront. I’m one of those people who needs it to be there upfront because I’ve tried dating guys I wasn’t really that attracted to, and I wound up miserable. (They were none too happy, either, that I wasn’t that into them!) Over time, as we date, I think we all kind of figure out which type we are, whether we can learn to be attracted to people or need to feel a certain level of chemistry right away.

  9. Simone Grant says:

    -Singletude
    I’ve never really thought of it like that – that some people have the capacity to develop attraction while others can’t. I’ll have to ponder that awhile.

  10. Mitre says:

    This would make a hell of a short story – expand and publish …


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