Lookin' for advice - Guest blogger: SWF

So, one of the unintended consequences of this whole adventure in online dating is that it’s quite a shock to the system to go from a complete and utter lack of romantic potential to winks, emails, and multiple dates over the span of one short week.  But, this is what I wanted, right?  Now, I’ve never been a serial dater, even in my younger, wilder, social-butterfly days.  Most of my previous relationships started slowly and blossomed from friendships - we were already buddies and one day realized we both kind of wanted to see the other person naked.  Sure, there were times where either the gentleman or I attempted (sometimes successfully, sometimes painfully not) to court the other in the traditional dating sense, but those were the exception. 

I distinctly remember a conversation with an old (male, non-romantic) friend of mine about how he was actively dating 2 or 3 women and how strange that was to me.  He was by no means cheating on any of them; he was legitimately dating them, by which I mean he asked them out for a specific activity, made arrangements, provided transportation, paid, and behaved like a true gentleman.  He eventually went on to marry one of those women, so I guess it worked.  That sort of experience is pretty foreign to me, so I’m struggling a bit with how to manage dates with multiple guys.  I mean, on the one hand, I have this mild fear I’ll end up in a Jack Tripper situation juggling two different dates on the same night – constantly excusing myself from one date to the other as I maneuver secretly from one end of the Regal Beagle to another. 

And on the other, more serious, hand, what if I really like someone?  Do I continue to go on other dates?  What if I go out with someone and the date isn’t spectacular, but we have a decent time and the source of our lackluster experience is probably due more to first date awkwardness than any fundamental mismatch?  Do I go out with that guy again?  What if he thinks I’m leading him on?  I’m not sure I’m ready to handle rejecting someone.  And I haven’t even begun to think about being rejected by someone. 

“Oh, SWF”, you’re probably thinking, “you’re getting way ahead of yourself, just enjoy this for what it is – getting yourself out there and meeting people”.  And you’re right, gentle reader, I am getting ahead of myself, but I wouldn’t be my charmingly neurotic self if I didn’t entertain these thoughts.  I just need to keep a level head, temper my atrophied romantic muscles from over-exertion, and, above all, enjoy myself.  But still, I ask you, dear internet, those of you with more experience in dating (online or otherwise), what advice can you give to this gal who has plunged herself headfirst into this new world?



  1. You do whatever you think feels right. If you really start to like someone, you probably won't even bother with other dates during that time, but keep everyone else on the backburner in case it doesn't work out. And go into EVERY date, just thinking at worst this will be a good story to tell.
    Have you gone on any yet?

  2. I try to give guys the 3-date rule (Unless it's a HUGE bust on date 1_ Give them 3 dates so you can try and eliminate that first date awkwardness. By then, you're usually fairly confident in your decision.

  3. @stephat1022 - I have! Will recap dates later this week.

    @Chrissy - That's fair. At the least a second for most, I think.

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