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

Learning The Hard Way

There are a lot of dating blogs out here on the interwebz.  Lots of blogs.  Lots of bloggers.  Lots of advice.  I don’t tend to give much advice.  And when I do it’s usually the product of a hard-learned lesson.

I’m willing to tell you what I know doesn’t work (because I’ve failed miserably) and what I think might be a better plan or way to go.  No wisdom of the ages.  No lectures on biological imperatives or the recent scientific data that might back my thesis.  Just my own trial and error.

With this in mind…  It was a few years ago.  I remember it was summer (I still remember what I wore on our second date, but I’m skipping ahead).  I had just returned to online dating.  Fresh from one relationship or another.  And I received an email from a man who lived in a city other than NYC.  I didn’t even look at his profile.  I just sent him a quick, “thank you but I’m only interested in local relationships” reply.

Shortly after that I received a message back.  I can’t recall what it was that he said that made me take notice.  But it was something.  Something smart or charming or special.  And I read his profile and became intrigued.  He lived in a city not too far from NYC.  Just a few hours away.

Anyway, let me both skip ahead and provide some background.  I was at a place in my old career where I was starting to get frustrated.  Starting to feel like I was nearing the end (and a year later I quit…),  He lived in a place I’d always thought I might be able to live, as an alternative to NYC.  And I’d had my heart pretty badly bruised early that year.

It sounds so bizarre now, but within a week of us connecting online we were having drinks not too far from my apartment.   He was officially in the city to visit family, but he made the trip to meet me.  We had a great time and I thought we really connected.  And then after our drink he walked me home and nothing.  No kiss.

Later, I found out from him that he didn’t want to be too pushy.  We spent much of the next two weeks communicating online.  He was moving very, very fast.  Even saying that he’d move to a part of his city that I’d like better (he was in the ‘burbs) if I moved there.  It was surreal, but also comforting as my last relationship had imploded because the guy was moving too slow.

And then he came for another weekend visit.  There was no pretense of him visiting family.  He came straight to my apartment.  Mind you – this was a man I’d never kissed.  I took him out to dinner to my favorite restaurant and from there everything went downhill.

He barely talked at all during dinner.   It was like a bad .  But I couldn’t make a polite excuse and leave early.  He was staying with me for the weekend, and just a few days earlier he was talking about moving to make me happy.

After dinner we went back to my place.  I considered, for several minutes, telling him that it was all a mistake and asking him to leave.  But I didn’t.  I felt I needed to follow through and see just how it all turned out.

The first kiss was awkward,   Like it never should have happened.   But instead of stopping we proceeded to the bedroom.   The sex was awkward, yes.  And also tense and bumpy.  (Yes, sex can be awkward, tense and bumpy.  Trust me.).

I was so happy to see him go the next day.  And then when I got the email from him, saying how much he missed me already, I didn’t hesitate to write a polite but firm goodbye.  I had no doubt in my mind that I never wanted to see him again.  That even the second date was a mistake.  That probably the first date was a mistake.  That I’d let myself believe things about him that had no basis in reality because it was convenient and I was vulnerable and it was easy.  But that the truth was the truth and it was time I moved on and lived in the real world.

I now have pretty strict about not dating guys who live outside NYC (and really, I mean to stick to them from now on) and even stricter about first dates and second dates and not getting stuck with someone out of sense of obligation.  But when I see people reference my , I have to laugh a little.  I learned the hard way.


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7 to “Learning The Hard Way”


  1. Singlegal says:

    I’m not one for the distance either. I dated a guy who lived an hour away and that just seemed too much. Every meet-up became an ordeal, and it really took week nights out of the mix. Fine at first, but not so great when you’re trying to move things along.
    We appreciate your trial and error. And I’m listening – I promise! :-)

  2. starangel82 says:

    I’ll drive about 45 minutes for a guy, but that’s about it. I really prefer 30. I’ve tried long distance dating before. Some people are, some people aren’t. I’m in the aren’t category.

  3. Veka says:

    I’m currently in this predicament myself. And my guy is about 2.5 hours away. And we both work M-F. I’m keeping my fingers crossed…

  4. bbbex says:

    It is so easy to idealize people we don’t even know. Glad it didn’t turn out to be dangerous for you. For me, I like to date people that live far enough away they won’t be “dropping by” unannounced, but close enough that it’s not totally inconvenient to do things with a little planning. I suppose one could accomplish that in NYC as it’s so big.

  5. Simone Grant says:

    Wow, that’s kind of funny. I don’t really see this primarily as a cautionary tale about dating someone who lives far away. That was part of the problem, but for me the bigger issue was that I developed a completely false sense of who he was – based on what I wanted to believe, rather than what was true. Like bbex said, I idealized him before I knew him (and the distance was a big element of that). And then when he was there, right in front of me I had to deal with the fact that he wasn’t the person I’d imagined.

    I know there are lots of people in happy long-distance relationships. I’d never tell anyone else not to try. I just know that for me they don’t work.

  6. Singletude: A Positive Blog for Singles says:

    I had a similar experience a number of years ago. I met this guy in a chat room, and we talked every night for six long months. (He lived about 10 hours away by car.) Then he flew out to see me and stayed for the weekend. He was…not the person I’d thought he would be. He was awkward and shy to a painful degree. And the truth is I think he was surprised by me, too.

    Like you said, the problem wasn’t the distance as much as the idealization that the distance allowed. When you live far apart, you don’t see each other much, and when you don’t see each other much, it’s easy to project a fantasy onto the other person.

    Also, there’s this pressure to have weekend-long “superdates” when you DO meet up because so much time has been invested in travel. That can lead to spending waaaaay too much intimate time with someone you barely know. In some of these situations, I have to wonder if part of the problem is the rushed nature of these superdates. For instance, in my case, maybe the guy wouldn’t have been so shy and awkward if we’d gotten to know each other the “normal” way, through a series of shorter dates, before jumping into a whole weekend.

    I won’t say that I’ll never have a long-distance relationship, but it would have to be with someone who was willing to go slowly and not have premature superdates, and that’s hard to find.

  7. Simone Grant says:

    -SIngletude
    I like that phrase, superdates. I actually think that what we each experienced is not that uncommon. It’s just not the kind of thing people talk about much. And so when it happens to us, we’re surprised by the outcome.