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

Good Daters and Bad Daters, Part 1 – The Good

I guess you could consider this a follow up post, as I’ve brought up the topic of good daters and bad daters before (most recently here and here ). I think it’s a topic that could use some further exploration.  Tonight I’m going to write about good daters.

I’ve gone out on a lot of dates in my life.  A lot.  More than I want to really guestimate.  It’d depress the hell out me. Unlike most women my age, I’ve never been married and never had a relationship that made it past the one year anniversary.  I’m pretty dysfunctional that way. I used to have really bad judgment in guys and like so many people do I relived the same, bad relationship over and over and over – just with different men.

I think my judgment has gotten better in the last couple of years, though not significantly so. I’m still working on it.  I can admit that.  A lot of what I end up writing about here are my thoughts on my history with men and the guys I’m meeting  and I guess I’m hoping the writing will help me process it all in some more coherent way and thus further improve my judgment. Heck, it can’t hurt. Really, I’ve shown some spectacularly bad judgment over the years.  I still remember when my last serious relationship was imploding, a dear friend of mine (the ex who took the half naked pics) said, “you didn’t really think that was going to last, did you?” It was obvious to him, just not to me.

Anyway, I’ve been on a lot of dates.  And like anything else, I’ve gotten better at it with practice. I can remember a time when I was really uncomfortable on dates.  When I was stiff and uncertain and insecure.  Now I’m good enough at it to hide my insecurities.  Those hundreds (probably thousands) of dates have given me some interesting perspectives.

When I’m on a and I’m having fun right away with a guy who seems just a little too good to be true I think of a great line from the musical Into the Woods. The character, Prince Charming says, “I was raised to be charming, not sincere.” Good daters are the Prince Charmings of the singles community.  They are fun and attentive and make the woman they’re with feel like a million bucks.  And if all you’re looking for is someone to date, I’d advise you to find a good dater and stick with him.

Just don’t expect one of these Prince Charmings to make any effort at building a long term relationship. They suck at that. And that kind of breaks my heart and always will. I’ve had the misfortune of falling for more than one of these guys.  And even more tragically, one or two of them seemed to have honestly fallen for me back.  It’s not that the Prince Charmings don’t fall in love and want a happily ever after.  They just don’t have the right skills to make it work. Invariably they behave poorly and self-destructively.

Now I’m not saying I won’t go out on a second (or third or fourth…) date with someone who’s obviously a good dater. I know some men who are genuinely smart and fun and interesting who are also more than that. Who are charming and sincere.  I believe there are guys who are good daters who like me want to grow into more than that.  But I also know enough to keep myself from getting too excited over a good first date.  It usually doesn’t mean a thing.


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5 to “Good Daters and Bad Daters, Part 1 – The Good”


  1. Anonymous says:

    If that “first good date,” leads to a second “good date,” and then a third,
    I’d say the chances are pretty good that eventually you would find out if this is a “keeper.”

    I guess you have to start somewhere. There is always going to be an upside and a downside and it seems we should have high expectations.

    But, when you’ve had so many experiences, and have reflected upon those downsides you cannot help but be on the look-out for the upside in every man. Experience, it turns out, is a great teacher.

    I’ve always tried to better myself with each relationship. There is someone out there, I know, just waiting for me.

    Best wishes,
    upon your next date,
    and always,

    Will.

  2. lisaq says:

    Lord knows I’ve had my share of recycled boyfriends, but I think I’ve finally broken out of the cycle.

    I still suck at first dates though. I’m sure it’s because, unlike you, experience is limited most due to geographic location. Well, and the fact that I’m on a dating sabbatical.

    I haven’t been out with many good daters though the one that comes to my mind was so good that he hooked me and broke my heart all in one damn weekend. *sigh* And so it goes…

  3. SINgleGIRL says:

    -lisaq
    Good luck with your continued dating sabbatical. I hope you emerge from it feeling refreshed. I’ve experienced one of those weekend whirlwind romances. OUCH! Having it end was like the worse hangover ever. Good daters – they’re dangerous fellows. Fun to talk to, great in bed, just don’t let them near your heart until you get to know them really well (and by then they’ve usually moved on).

  4. Hammer says:

    I totally fall into this good dater category. And you’ve 100% nailed me as well. I’m terrible at relationships. Getting the girl is no problem, keeping the girl is still a work in progress.

  5. Elizabeth Andrews says:

    I’m a sucker for charm but as I’ve gotten older am much more wary about falling for it. Just hit 40 and have only had two long-term relationships (of two-year and one-year duration) but have been on hundreds of dates. I’m VERY good at dating but sad about the lack of long-term…