100 Emails, 20 Dates An SF girl's systematic quest to end her singlehood

Can I Really Handle a Fling?

For a while now, an old coworker and I have been flirting up a storm. We'll meet up for drinks every so often, sometimes later at night, and although it's been strictly platonic so far, there's definitely an electricity between us. And also a deep awkwardness. J. and I have known each other for a while. That whole group of coworkers is still friendly. It would be weird.

A few weeks ago, at a friend's party, he barely left my side. The more we drank, the more he talked. "Why do you have to be so hard to get?" he asked. "What do you mean?" I said. "I've been trying," he said, as if the effort was almost painful. "All you need to do is ask me out," I told him. "Fair enough," he said, sounding a little deflated.

That sort of thing -- and many more obvious exchanges -- continued for the rest of the night. I emailed him a few nights later, after I'd been out:

I apologize in advance if a) this is incoherent or b) I have deeply misinterpreted something, but I feel that there are numerous threads of conversations that we started Sat. night that maybe should be finished. So let's finish them. Sometime. Sometime soonish.

His response: "Did I miss a booty call?" Sure, he was avoiding the topic, but it was kind of funny. I laughed. I admit it, I had developed a big crush on him. He's a good guy, he challenges me intellectually, we make each other laugh, he's good-looking, and he was complimenting me non-stop. What isn't there to like?

More flirty emails were sent back and forth, until finally, we went out for a drink recently. We made awkward small talk at the bar. We finished our drinks, I invited him in to my house, we made less awkward small talk. And then he said, "So it sounds like we have some unfinished business to attend to." He took off my shoes then took off his own, and we faced each other on my couch.

I laid out my position: It would be weird, yet I was definitely attracted to him and I definitely liked him. I told him I thought he was a good guy. And I said that part of me felt that we should just kiss and see if the whole thing has any legs before we let any of our mutual friends know.

He laid out his position: He's definitely attracted to me, but he's not convinced that things would work out between us. And he absolutely didn't want anyone getting hurt. He agreed that it would be weird if all our old work friends knew, so we'd have to keep it to ourselves for a while. And with that, he pulled me towards him and started kissing me.

So we kissed. And like our small talk that night, it was awkward at first, and then it was more fun. Then it was really fun. When he left, he gave me a great goodbye kiss. I may have swooned slightly after I closed the door.

It felt so good to get that out of my system: months of build-up and then this nice, fun release. The intensity of my crush had, thankfully, abated. And for almost an entire day after, I thought, "A fling could be fun. I could do it!" I've never had a fling. It felt exciting. I would do it on my own terms, of course. We wouldn't get too serious physically, and I'd stop the minute I felt like I was starting to develop feelings for him. I felt empowered by it all.

But then I reexamined the evidence:

• He was an hour late (he was meeting me at my house). I texted him after a half hour, and he apologized. But still.
• All his flirting has been pretty forward. Most of it was about how he thinks I'm hot. None of it was  about my personality.
• I like him for who he is and who he is to me as a friend. His hotness is secondary to me.
• Our "conversation" about a potentially awkward subject consisted of about six sentences.

In those terms, it's obvious, even to oblivious me. Things are starting off so imbalanced, that I'm definitely going to get hurt. I know he's not using me (see previous references to mutual friends, who would kick his ass if he did, and to his being a generally good guy). But he's just looking for one thing. And I'm looking for another. Kissing him, as fun as it might be, is not going to move me forward in my goal and will likely hold me back.

So, as sad as I am to admit it, I've realized I'm just incapable of having a fling. And it sounds like he's either incapable of or uninterested in giving me anything more. Oh well. Sorry, J. I'll have to break the news to you next time I see you. I plan to look fabulous, just to make absolutely sure you know what you're passing up. But we'll still be friends, man.