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

Good Date, Bad Dater

I twittered about most of this (twittering – so bizarre), btw.

I was starting to get annoyed with the freelancer.  We spoke briefly last night and left it that we were going to have dinner tonight.  No where or when.  We were going to speak sometime today to confirm the details. That kind of thing annoys me.  I prefer it when a asks me out with a complete plan, e.g., “How’d you like to go out to dinner Friday night?  Is ____ OK with you? Great. How about 7:30?” As of 3pm today we still had no set plans.

So, I texted him and after a few awkward back and forths we had our plans. We were meeting at 7:30 and so I had time to run and change after work (And attempt to do something with my hair.  It was such a bad hair day.).

So, he’s a bad dater but in a very sweet way.  I can’t actually remember the last time I met a guy who was so genuinely uncomfortable on a date.  But he’s easy to talk to and holds up his end of the conversation well.  I actually can’t figure out why he’s so uncomfortable, he’s cute and smart and successful – all the good stuff.  Just no confidence.

After dinner we went for a walk.  It was a beautiful night.  Here’s a pic.

Good Date, Bad Dater dating update

We walked for about 30 minutes and then it seemed silly to walk anymore. It was pretty clear that he wasn’t going to make any attempt to kiss me or even hold my hand.  I hopped in a cab and came home, first telling him what a great time I had.  And I meant it.

He sent me a lovely email just a few minutes ago.  He said I looked fetching. There’ll definitely be a third date.


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7 to “Good Date, Bad Dater”


  1. Miss Heather Leigh says:

    Heh, reminds me a lot of my boyfriend. I certainly wish you the best of luck! I scored really well with a “bad dater.” Trust me, some of the bad daters turn into good boyfriends. Best of luck!! :)

  2. cjw666 says:

    I do agree with miss heather leigh. You sound like you definitely want to persevere anyway.

    Maybe you’re going to have to casually take his hand at some point and see if it encourages him. Depends how you do it of course, or you could scare the hell out of him ;)

  3. One Time says:

    Maybe you should have given him a hint?

  4. SINgleGIRL says:

    miss heather leigh, cjw666 and one time – I think you are all right. I will post about this in a little while. Am getting a late start this morning (hard rain in NYC today and it’s making it hard for me to move) but will get to it soon!

  5. Hammer says:

    Where are you finding these emasculated guys? A woman needs a man who can lead her and make her feel safe and like he’s in control in order to feel that lower brain attraction for him. I don’t get it.

  6. SINgleGIRL says:

    -Hammer,
    It’s funny you should say that. I’ll be posting something VERY relevant later today,

  7. bobbyboy says:

    I actually can’t figure out why he’s so uncomfortable, he’s cute and smart and successful – all the good stuff. Just no confidence.

    No confidence is part of it. With guys like this, time is a great way to get to know them.

    Where are you finding these emasculated guys?

    Sadly, this inaccurate view just fuels difficulties for woman in the dating scene.

    Glad that you had a good time though :)