Serial Dating Does NOT a Relationship “Expert” Make

LucyYou might have noticed that I’ve cleverly avoided the subject of my love life for the past few days.  This is because it’s easier to offer my opinions of “hooking for food” than try to make sense of… well, whatever it is that’s going on in my life.

I’m always amazed when friends come to me for relationship advice.  Sure, I’ve gone on my fair share of dates over the course of the past year and a half (okay, maybe more than my fair share—70-something dates with 30 men to be exact—not that I’m counting) but relationships?  Relationships aren’t exactly my thing.

I went from serial monogamy (with a penchant for long distance relationships of the international variety) to serial dating.  Now, thanks to marvels of modern technology (i.e. Match.com and an Excel spreadsheet), I’ve been able to line up five first dates in as many days.  And although it’s been a while, I’ve even dated two guys in the same day.  I’m not exactly proud of this fact but nor am I terribly ashamed of it either.  (I did always go home in between to change outfits.)

Considering the circumstances, I’m in no position to be doling out relationship advice.

This is because relationships require work.  And why work to build a relationship when you could just as easily slip into a new pair of heels, log back on Match.com and find someone else?

Now dating advice, on the other hand, is a different story.  I love dating.  I love every bit of it, from the part where you stand in front of your mirror trying on sixty three different outfits (only to discover that you’ve now completely destroyed your bedroom), to the awkward hellos and hopefully less awkward goodbyes.

After a six month stint on Match.com, another six months on eHarmony and an ill-conceived subscription to Plenty of Fish that’s turned into a lifetime membership because I still can’t figure out how to cancel (206 unread emails and counting…), I consider myself more than qualified to give dating advice, and I have, on many a happy occasion.

But when my single friends come to me for relationship advice, I just shake my head and ask, “Have you seen my track record? Don’t you know I’m still single?”

I used to think this was because I’d lost my touch.  I had boyfriend in high school, college and grad school but maybe I had forgotten something along the way?  No matter what I did, it seemed, my budding relationships would always self destruct around the fifth date, and once I realized this was happening, it because a self-fulfilling prophecy.

(In 30 men, I’ve only passed the fifth date mark on three occasions.)

Over the years, I’ve come to recognize that my girlfriends and I (and probably most women) tend to put a lot of stock into the whole friend vs. girlfriend thing.  When do you make the switch?  How do you make the switch?  Is it okay to ask someone out via Facebook if you’re past the age of… say… 12? (Methinks not.)

But the real question isn’t about the title, or even when you upgrade (or downgrade) from one title to another.  The real question is how you go from dating, and all of the associated cocktails, chemistry and inadvertent first date hook ups, to being in a relationship.

This, I’m beginning to realize, is where the going gets tough.

And seeing as I’m rapidly approaching the fifth date mark with The Wedding Date while Date #7 continues to orbit somewhere in the periphery, I’m finding the “going” even tougher than usual.

9 Responses to “Serial Dating Does NOT a Relationship “Expert” Make”

  1. Zak

    “…how you go from dating, and all of the associated cocktails, chemistry and inadvertent first date hook ups, to being in a relationship.”

    So, I wondered that myself, with Ms. D. We kept going out on dates, but it never felt like dating (at first). In my heart I was totally, 100% into her, but I was still wondering when, and if, I would have flip back to my serial dating ways (it really does become too easy to do that, doesn’t it?).

    Next thing I know, BAM!!!, I’m calling her my girlfriend (and flat out scared she’d disagree, but she didn’t). Where the hell was the switch?

    I think it just happens. You lose track of yourself and all your senses and you’re having such a good time, it just happens. Like watching TV late at night and your eyes are heavy. You don’t know when you fell asleep, just that you did and now the credits are rolling. And just like rolling over to go back to sleep, you stop thinking about it and keep going with the person you’re now in a relationship with.

    Reply
  2. Philly Tap Teaser

    When both people decide they don’t want to date other people and that they see some sort of future (no matter how brief) with the other person? That’s when I always thought the shift to “boy-friend” happens?

    Reply
  3. Oh, my roaring 20's...

    I just have to say, I adore this blog. I’m not exactly a serial monogamist, nor was I a serial dater… but when I am in a relationship, it’s definitely long term. And now it’s become permanent, and while I am perfectly happy being engaged and planning my wedding, I love reading your adventures and somewhat living vicariously through you!
    You always have an interesting perspective… and you make “serial dating” look classy. I really appreciate that, because my previous notions were pretty negative on the topic. Your dating chronicles have completely changed my own perspective.
    Though I am dying to find out what’s going on with the Wedding Date and Date # 7! 😉

    Reply
    • Kat Richter

      Thanks! Serial dating can get pretty damn sticky (which is why we’re ALL wondering what’s going on with The Wedding Date and Date #7, myself included) but I do try to keep it classy 🙂

      Reply
  4. taramyers1987

    What I don’t like is that you have to pay for match or eHarmony. Online Dating should be 100 % free. The few free dating sites are full of players though, no one seems to want something serious.

    The only free dating site with serious singles I found was on Have you tried TheDatingElement.com?

    It is a 100 % Free Dating Website made for serious singles worldwide.

    Reply

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