The Dateable Dork

There is a very fine line between innocent flirting and not-so-innocent flirting.  Sometimes the line is blurry, and you can’t really tell exactly where it is.  Sometimes you really don’t know whether you’ve crossed it or not because everything is so up in the air.  You can make excuses for yourself, because really, how can you tell if you crossed the line when you can’t even define where it is?  Other times, however, the line is so rigid and clear that you can pinpoint the exact moment when you cross from one side to the other, from the innocent side to the not-so-innocent side, from the accidental to the deliberate.  And last night, I very deliberately and purposefully crossed the line with the new male prospect.  I am simultaneously regretting it and loving it.  I’m hesitant but excited.  There is a very fine line between the acceptable and the unacceptable, and today, the adrenaline rushing through my body is telling me that I’m a bad, bad girl… and I think I like it.

The new male prospect and I have actually been maintaining our totally platonic friendship pretty well these days.  We’ve been catching up over the phone every few weeks, just shooting the shit, talking about work, life, family, etc.  He’s been dating his girlfriend (aka Thursday night girl, whom he met last summer) for about six months now, and he genuinely sounds happy.  And I’m genuinely happy for him, particularly since he’s been through some rough shit and, frankly, deserves a good, solid relationship for a change.  The new male prospect is the only person I talk to about the details of my recent health problems (aka the never-ending mysterious plague), and I’m the only person he talks to about his relationship and family issues.  It’s actually been really, really nice catching up with him, and I feel like we’ve really developed a healthy friendship that we mutually benefit from.  I was patting myself on the back for actually being an adult.  Well done, DD.

That is, until last night.  The new male prospect and I had one of our usual catch-up chats, and for the first hour or two, things were going pretty much according to plan.  We talked about all sorts of random stuff, the holidays, how work still sucks, how both our brothers are surprising still married, etc.  It was nice.  I asked how things were going with Thursday night girl, and he said that it was going really well and that it’s such a nice change of pace for him to have a stable, meaningful relationship.  I told him it was adorable and that I’m really happy he (finally) found someone that he really connects with.  And then he paused… and then he said that although he’s happy with his girlfriend, there’s a part of him that missed the excitement of dating, the thrill of the hunt, the adrenaline rush of casual sex and meaningless hookups.  And then I could see the line in the distance, slowly approaching…

I tried to be a good friend.  I told him how it’s perfectly normal to have those kinds of feelings, especially during the transition from casually dating someone to starting a meaningful, monogamous relationship.  The difference is that although you may fantasize about other people and other events, you consciously make the choice every single day to not act on them, to stay with your girlfriend, to hopefully trade in the thrill of the hunt for something so much better, so much deeper and more satisfying.  And there’s no reason you can’t be having amazing sex in a monogamous relationship.  I told him that he needs to decide if these feelings are really bothering him and are a sign that something is wrong, or if they’re just what they are – fantasies – and that he’s committed to and truly happy with his girl.  And then the line got a little closer…

Now, my dear readers, I like to think that I know the new male prospect pretty well at this point.  We’ve known each other for a while, and I know all the little nuances in his voice and the meaning behind the words he chooses.  (I’m sure his girlfriend knows him even better, but that’s besides the point.)  And as he’s telling me that he’s 90% committed to his girl and 10% dying for a random hookup, I could see exactly where he was going way before he actually got there.  I could hear it in his voice.  And I mean, seriously, it was pretty obvious from the direction this conversation was going.

He tells me that he doesn’t think about his girl when he masturbates, and instead, he fantasizes about hooking up with random chicks.  I tell him that’s perfectly normal and not to worry about it.  Then he tells me that sometimes he masturbates to the thought of this girl that he went on one date with over the summer who “had a nice rack.”  Again, I tell him that’s normal.  I ask him if that girl were to show up at his door right now, would he jump her, or would he stick to his relationship with Thursday night girl?  He hesitates in answering.  Then he tells me that, well, you know, he kinda sorta thinks about hooking up with me when he masturbates.  And now I’m standing on the edge of the line.

I say, “Oh god, do we really want to talk about that?  I’m not saying anything.  You have a girlfriend.”  And he says, “Remember when you and I hooked up over the summer?  You came up to my place and I practically jumped you on my couch, and then you got mad at me and left, and a week later you changed your mind and I found myself driving to your apartment in the middle of the night for the best oral sex I’ve ever had?”  And I say, “Umm, yeah, of course I remember…”  And then we started talking about sex.  And we tip-toed all over that fucking line.  And I got so fucking close to the line that I could fucking taste it.  And it was fucking good.

Then he stars suggesting that since I’m not really in a place to be dating right now, I should just casually hook up with guys for the hell of it.  I told him that I don’t want casual sex, but maybe I could just give blowjobs or something.  I love sucking cock, after all.  Then I say, well, if I have no intention of sleeping with these guys, I doubt they’d stick around just for the blowjobs.  And the new male prospect says, “Oh, they’d stick around all right.  You’re that good.” 

And as I looked down at the starkly drawn line in the sand, I deliberately and objectively walked right over it.

We certainly didn’t do anything last night (we were just talking over the phone, after all), and nothing was explicitly said, but from that moment on, the flirting was decidedly less than innocent.  It was all in our tone of voice – the way he laughed, the way I’d pause before answering, the way he’d imply something and then I’d subtly let him know that I understood exactly what he was talking about.  It was all so fucking hot.  The conversation got very sexually explicit, but there was no mention of us hooking up, no mention of cheating on his girlfriend, no mention of making the long drive from one apartment to another.  But it was all just below the surface, and the line was definitely crossed.  I felt guilty about blatantly flirting with someone’s boyfriend.  I felt guilty for enjoying flirting with someone’s boyfriend.  I felt guilty for thinking about him after we hung up last night, and I felt guilty for absolutely loving the fact that he jerks off thinking about me instead of his girl. 

The line was definitely crossed. 

But here’s the deal: the new male prospect and I had just spent two hours talking about how he’s missing the excitement of casual sex, and here he is creating a little excitement for himself, and here I am playing along with it, stroking his ego, and all the while creating a little excitement in my own practically non-existent dating life these days.  It’s all so easily explained.  This is not rocket science.  I can come up with excuse after excuse.  But the truth is that we both consciously made an unspoken decision to cross that line last night, and although I feel really guilty about it, I am absolutely loving it. 

The new male prospect and I have always had a very strong physical, sexual chemistry.  It’s been there since the day we met, and it will probably always be there.  And I guess last night we were both looking for something that we knew we could find in the other person, and we just went with it.  The new male prospect wanted a temporary escape from his relationship, and I wanted a temporary escape from my lonely existence.  All I can say is THANK GOD we live so far away because I don’t know what would have happened if we still lived close together. 

A part of me really wants to send him a flirty little text tonight, and a part of me keeps checking my phone to see if he sent me something.  Then again, I know neither one of us will do anything because he’s happy with his girl and I completely respect that.  But DAMN, the thought of him masturbating to the thought of me sucking his cock is just about the hottest thing that’s crossed through my mind in quite a while.  I might just have to return the favor tonight and do a little fantasizing of my own…