Does it work to mix work and dating?

I met D at a party. I was there with Ryan Paugh and a few bloggers from the Brazen Careerist network, and because it was SXSW and it was all parties all the time, I was pretty partied out. But the party was for Kirtsy, and I love the women who run Kirtsy, so I went.

Also, Holly Hoffman wanted to meet Guy Kawasaki. And really, it’s not like I’m his best friend, but because I know him, I could say to Holly, “Oh, I’ll introduce you.” And I did that. And Holly was thank-you-thank-you, even though Guy is so nice that you can just walk up to him and introduce yourself and he’ll be nice. To everyone.

And I’m standing there with a bunch of 25 year olds, because I’m always hanging out with 25 year olds because that’s basically my job—I work with them and my business is for them. But I was not with THE 25 year old because the night before, I woke up to him peeing on the carpet in my hotel room.

When I asked what he was doing, he said, “Oh, sorry” and then he went back to bed. So I woke him up. And yelled at him.

He said he was drunk. He went back to sleep. I woke him up. I said, “I told you you had to go down on me and you didn’t. You asked a woman out after she wrote a whole blog post about oral sex and you don’t even do oral sex.

I’m pissed.”

He says, “I was too tired.”

“Too tired for ten times? We’ve had sex ten times.”

The night deteriorated and I told him to leave the next morning, by 8am.

He says, “Can you wake me at 7:30?”

And I say, “No, I’m not your mother.”

So at the party, that night, I was surrounded by 25 year olds, but not that 25 year old, and you can imagine that I was really happy when someone my own age came up to me.

But I really couldn’t tell why he was coming up to me. I have said before that I think I have Asperger Syndrome, and I think it’s full blown when it comes to dating. So I have to be direct. So when this guy who is clearly in my age bracket comes up to me and says, “Hi, I like your blog,” I ask, “Are you trying to date me?”

I know this is not normal. But I had been to a million parties and I had had a glass of wine, and I just wanted to sort people quickly.

He thought for a minute and then he said, “Yes.”

Great, right? He showed me that he can cope with my weirdness and still come out okay. So we hung out talked for a while, and then I realized my phone was dead. And the night was early and I needed to text people and so I wanted to go back to my hotel room to get my charger.

The guy said he’d walk there with me.

I tell Ryan Paugh because I think maybe I’m missing something.

Ryan says, “He thinks you’re having sex with him.”

“What?”

“Yeah. You can’t take a guy to your hotel room and not have sex.”

“Oh. Wait. But I told him I need my charger.”

“No.”

“Okay. Okay.”

So I tell the guy, “No.” Then I walk him over to his friends, who are at the same party, and I tell them our date is over: “I’m getting my charger and he can’t come with me because I don’t want to have sex with him.”

His friends laugh.

I think this is a good sign.

So the next night we have a date. It is very low pressure because he is from a state that is far away and does not have a direct flight from Madison. And he is not a gazillionaire, so he is not going to buy a house for us to share in Chicago when we meet at O’Hare. So: No future.

I tell him, “Be careful of that wet spot on the floor.” And then we have a one-night stand. At least I think it is going to be a one-night stand. But then in bed, I can tell that he’s not thinking one-night stand because he does sweet things that guys never do to me, like stroke my hair. I do that with my kids.

And then things deteriorate quickly. Well, for three weeks, things are good. I like him and I call him. And I see him again. Then things get bad because he twitters about me. And I think, I do not want the world to know I’m dating him because maybe I don’t want to be dating him.

And he tells me I’m out of my mind that I’m worried about who is twittering about me. He says something, which I will summarize as: Get a life.

So I am not with him. Because you can’t be with someone who thinks you’re out of your mind. And I’m not with the 25 year old, who, by the way, is also twittering about me, in an odd sort of way.

So I’m thinking the lesson here is that if work and sex are mixing then it’s a sign the dating isn’t working. But really, there must be a ton of people who think sex and work overlap because, look, my blog has 33,000 subscribers.

So maybe the lesson is I shouldn’t date people I meet through my blog. But then I think, who have I met not through my blog in the last two years? And maybe the answer is no one.