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

Two Out of Three

I had three dates on the schedule for this weekend: my Friday night with The Musician and then 2 first dates on Saturday.

The second date with The Musician went very well.  We were supposed to have dinner at a place not too far from where I live.  It was his choice.  I’d never been there before because it has a reputation for being insanely crowded pretty much all the time and I don’t like waiting. Anyway, I got there a couple minutes after he did (not late, just a couple minutes after he did) and he’d found out that the wait was already up to 90 minutes for a table for two.  We agreed that was crazy and I suggested someplace else on the same block.  Actually, one of my favorite restaurants.

We have a lovely meal and great time.  Our conversation was easy and fun and yet we managed to talk about some pretty serious topics.  We’re just pretty easy-going around each other.

The food at this place is great but kind of on the heavy side and so neither of us wanted dessert.  I was kind of hoping he’d suggest that we go someplace for drinks afterwards because it was still pretty early when we left the restaurant, but he didn’t.  Instead I let him walk me home, knowing full well that I wasn’t going to invite him up.  As nice a time as we’d had, I knew it would be a mistake to invite him up.  He’s about to leave on a two week vacation.  Sleeping with a guy on the second date who’s about to go away for two weeks is just a sure fire way to make things more complicated than they need to be.

We stood outside my building, talking, for a while.  He didn’t make any kind of move and I really couldn’t read him.  Was he just waiting for the invitation?  Probably.  I guess so.  But it was wicked cold and so if I was going to invite him up you’d think he’d have realized it wasn’t going to happen after two minutes and said goodnight.  Finally it fell to me.  I said, “Well, I’m not going to invite you up tonight.“  I stressed the word tonight so that it was clear that he was sure to get an invite soon.  And then I told him thank you and I had a lovely time.  He gave me a quick, very chaste kiss and left.

The next morning I was thinking that maybe I handled it poorly.  I just don’t know anything anymore.  I feel like my judgment must be wrong (especially as I post the Ex Files and review/remember the beginnings of that relationship-at the time, I thought everything about those first few dates was perfect and that didn’t keep it all from turning to shit).   I sent him a brief, “thank you” email to which he replied with a thank you of his own and invited me out tonight (he leaves tomorrow).  I couldn’t go because of other obligations and so that’s that.

On to yesterday’s first dates.  I had two scheduled – one for 2pm and one for 6:30pm.  The one at 2pm was with one of the potentially too young guys I mentioned on Twitter (for those of you who follow me there).  He’s 38 and you know what – I can honestly say that yeah, he seemed really young.  He didn’t online or on the phone but in person he came off as really immature and insecure (and yeah, he might still be that way at 48).  He was smart, funny, cute but his insecurity was a real issue.  He was one of those guys who was constantly pointing out how much smarter and better he was than everyone else.  Oh, and name dropping.  Which I really hate.  I don’t care who you know.  Really, I don’t.

My 6 o’clock date was a real nightmare.  He suggested we meet at a bar in my neighborhood which I thought was very thoughtful.  Then he mentioned a couple that he knew.  One is just barely in my neighborhood, it’s actually too far to walk to.  The other is one of my least favorite places.  It’s cold and loud and overpriced.  But he said he liked it and so I said I’d meet him there.  When we were making the plans he said, “It’s on ___, right?”  And then he mentioned the wrong avenue.  I corrected him.

Well, he called me at 6:40 to say he was sorry but he was running late.  I told him it was OK.  I grabbed a seat at the bar and started without him.  He called again at 6:50 to say he was lost.  He’d gone to the wrong avenue.  I corrected him again.  I left the bar at 7 and started to walk home.  When I was a block away I called him and told him I was on my way home.  He had a fit on the phone.  He said he was there and asked me to come back.  I told him I wasn’t really in the best of moods anymore and just wanted to go home and would be willing to try another time.

He was kind of an ass on the phone.  It wasn’t his fault he was late. It was the subway.  And he didn’t have the right address. And….  And I should give him another chance.  And I should come back.  And the more he talked the less I wanted to listen.  If he had just said, “I’m sorry things got screwed up.  Can I make it up to you?  Tonight or any other night?”  Then we would have been cool.  But instead he came off as a spoiled child.  And then later than night sent a follow up email – half apologizing but half saying it wasn’t his fault and so I should give him another chance.  Who knows, maybe I will?  Maybe the pickings really are that slim.


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11 to “Two Out of Three”


  1. Seth Simonds says:

    Good on how you handled the 2nd date. That’s a smart maneuver and I don’t think it matters how you said the words as long as the results are positive. And they are.

    You already have a very good view of what spoiled boy will do whenever things go wrong. He flipped out over getting lost…what do you think he’s going to be like when he gets angry about real issues? And then he emailed? ahhahaha.

    Send him packing.

    =D

  2. darkheath says:

    Sounds like an interesting weekend. As far as #3, it’s not the lateness or the “wrongness” that’s the problem, it’s how he acted afterward that’s the true “tell” in this case. It’s little clues like that that show more about a person than anything.

  3. terrablack says:

    On Fri. date –I don’t think you handled it poorly, you were up front and honest….

    On your 2pm date —I hate it too when guys name drop like it makes them better when really it shows how insecure they are.

    On your 6pm date –I can’t see giving him another chance…not because he was late, things do happen, but because of the way he responded. I can just see him acting childlike whenever there is a disagreement or problem… not cool at all.

  4. darkheath says:

    terra black, i like your logo. stylish, simple and elegant. what’s it for? a company or personal?

  5. tommytrc says:

    Being stood up on a date is the pits. He missed his chance, unless he comes crying back with some expensive shoes or jewelry, send him packing.

  6. terrablack says:

    Thank you darkheath, it’s personal… for my fashion & style blog

  7. recklessstudio says:

    Alright, well you know what? I read your tweets about that evening date and I don’t blame you. Like darkheath said, it’s not about what actually happened. It’s about how he reacted. If you ask me, he doesn’t get another chance. He blew it the moment he was late, in my opinion.

    For any guy that goes out on a first date, you better be on time. And know where the hell you are going. Realize that not having your shit together reveals how irresponsible you are and how you don’t pay attention to details.

    The second date with the musician seemed pretty normal although, I feel like it may have been a step backward because there didn’t seem to be any type of advancing. But considering the circumstances, you did well. Hopefully, there will be some tension and anticipation when he is gone so that when he gets back, things can really get going.

    And as far as immaturity goes, for someone who is 15 years younger than that guy, I would have a zero-tolerance policy for such nonsense. I would only hope that by the time you reach that age, you have your shit together and know how to conduct yourself in front of quality women (such as yourself).

  8. cjw666 says:

    Jerks are jerks and, when it all goes belly up you can immediately see them for what they are because they handle it so badly. Don’t bother with more.

    As to your decision with the musician, I’ve never been a fan of rules about first dates, second dates, or any other date – I think it’s all down to what you feel at the time. However, whether it was the right or wrong way to handle it at the time doesn’t matter a damn – if you have anything between you it’s bigger than stuff like that and you’ll be able to discuss it with him sometime in the future – in bed.

  9. starangel82 says:

    I think I would have reacted the similarly with all three dates.
    1. I think you handled the situtation well. If you don’t want him to come up then you don’t invite him up. Going out with someone doesn’t guarantee a trip to the bedroom. (Although I’ve met several guys who think it does.)
    2. I can’t stand when someone acts immaturely. I know everyone grows and develops at different rates, but there comes a point in time where we all have to grow up.
    3. Drop him. I could have handled the being late. It happens. Like everyone else has mentioned, his reaction is the telling part about him. More than likely, he’ll always react that way when something goes wrong or he doesn’t get his way.

  10. bobbyjensen says:

    I think you handled it all quite well. I wouldn’t second guess anything you did.

  11. SINgleGIRL says:

    Wow – such amazing comments from everyone. Thanks so much. I wish I could’ve responded earlier but having been working out of an office that blocks my site for that last few days (ugh) and had family stuff yesterday. Anyway, there’s news to report and so instead of responding to any specific comment (And, again, thank you all for your comments. I need to hear the unified – don’t do its) I am going to wrap it all up into a post later today.