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

“When Harry Met Sally” syndrome

When you have friends--especially good friends--of the opposite sex, the "What if?" thought is going to pass through your head. If, when you have that thought, you realize that you're attracted to the friend, it's going to become a crush. In college, I dubbed this the When Harry Met Sally syndrome. I don't think of it as a bad thing. After all, isn't this the ideal? Finding a partner who's your best friend too?

On Friday night, I went to see It's Complicated with friends, then we met up with some of the bros at a bar. They had been drinking since happy hour. We got there at midnight. A bunch of people went out to dance, and P., who I had a friend crush on earlier in our friendship, said, "Put down your things, we're dancing." I put down my coat and kept my purse on my shoulder. "Put down your bag," he said. I said, "No, it'll get stolen." He asked what would be the worst thing to lose, and I said my keys, because then, after losing everything, I wouldn't even be able to get into my house. "Hand me your keys," he said.*

"I hope you know this doesn't mean we're sleeping together tonight," he said as I handed him my keys.

Insert sound of record screeching to a stop. "What?" I said, mind racing as I turned back around to close my bag. "Where did this come from?" I wondered. But also, "FINALLY! A chance to find out if he ever liked me."

"So the thought has crossed your mind?" I asked.

"So many people have asked me why we're not dating," he slurred.

"Like who?"

"So many people," he repeated, in that frustrated tone drunk people have when they're fighting their beer-soaked brains to try to communicate something genuinely important. "I love you, N. I mean, I really love you." He gave me a huge hug, then kept one arm around me. He gets really lovey when he's bombed. "I have mad love for you. You are one of my favorite people. I want you to know my family, my friends--I don't do that with just anybody." He stopped and gave me another giant hug. "But," he began regretfully, leaning in closer, "I like Asians."

Which I knew all along, and which is why, when R. insisted that he liked me (when he was in another drunk lovey state), I knew he didn't.

At first, I was disappointed. The guys who I think would be a good fit with me either don't find me attractive or just want to hook up. But today, I woke up and saw it differently.

The three friends I've had crushes on in the past two years have a lot in common: they're all really smart, fun, thoughtful, and, in general, exceptionally good guys. But they all represent different things:

• A.: One of the smartest people I know. It can be a challenge to keep up with his brain, but it never feels like a competition. I love people like that.
• J.: There have been times when I've started to freak out about things, and he just puts his hand on my shoulder. Suddenly I feel calmer. Very subtly, he accepts where I am emotionally--without judgment--and points me in a more productive direction. He's the one who made me realize I need this kind of emotional balance in my life.
• P.: I've had deep conversations with all of these guys, but P. and I have been really honest with each other, and I love that about him. But he's also really, really fun. When he rallies people to go out, you know you're going to have a great time. He's more outgoing than me, and being around him help me be more outgoing.

Those guys' reactions to me have been equally telling:

• A.: Respects me for my intelligence and sense of humor. I feel smarter and funnier around him, and I feel safe enough to take risks, because it's OK to make a joke that bombs around him.
• J.: Totally had the hots for me. It was disappointing that that was all he felt, but I'm trying to look at the positives here. It was nice to be wanted.
• P.: Sees me for who I am and loves me for it.

So what I need, really, is these three guys rolled up into one. But the fact that I've found three great guys over the past two years who are almost perfect for me means I've figured myself out enough to know what kind of guy is going to bring out the best in me and what kind of guy I'll be the best partner for. Now, I just need to find him.

If you see this bag (only with 2 straps instead of one), please let me know

Full disclosure: This post was equally inspired by the Friday-night conversation and a Taylor Swift video that Kristin posted. Which does of course beg the question, why do I so closely identify with the emotional life of an 18-year old when I am twice her age? (That was a painful sentence to write.)

*My purse was, in fact, stolen, somehow while we were standing right in front of it. I should have trusted my instincts. If you see a bag that looks like this photo (right), but has two straps, it's mine. Seriously, no one else in San Francisco has this bag. If you can get it back, I will pay you a reward.

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.