I met Tom online one Saturday evening. He was at a bar in San Francisco for a friend’s birthday party. I was home, sipping cheap wine and watching Sex and the City reruns.

One of us was not pathetic.

We started chatting, I was immediately intrigued, and turned off Carrie and crew to focus on our conversation. He was funny, witty and apparently bored with the drunk people around him, so he struck up a texting conversation with me which turned into a phone call from his car.

I quickly learned that Tom is a recovering alcoholic who recently celebrated 20 years of sobriety. He was willing to endure the bar scene for the sake of his buddies, but once everyone around him was inebriated, he lost interest. Thus, the phone call to me from his car at 10:45 p.m.

We talked for a while and decided to meet the next evening. He was cool enough to suggest meeting at a wine bar where he wouldn’t be partaking, of course, but I would be able to have a glass of red while he sipped on ice water.

The next night, we conversed, we sipped, we laughed–everything went swimmingly. He was cute, and I choose that word specifically because he wasn’t hot nor was he handsome. He was . . . cute. A 49-year-old who seemed to still be channeling his inner 19-year-old. He’d never been married, and didn’t want to be. He had replaced his addiction to drugs and alcohol with an “addiction” to live music and concerts. He was having fun living the life of a die-hard bachelor who got to rock out whenever he wanted. He’d almost died at 28 when he quit drinking and drugging for a day in order to be sober for his dad’s birthday, and he was grateful for each morning he woke up breathing.

So after the wine bar, I took this cute 49-year-old rock star to my car and I became 16 again. We made out like a couple of teenagers–but I’m pretty sure they don’t make cars now like they did in the 80s. It was cramped, uncomfortable and awkward. That’s when I broke one of my biggest first-date rules.

“Maybe we should go back to your place?”

Did I say that out loud? Yes. I did. And I about died of embarrassment. How wrong and, let’s be honest, how cheesy.

We both knew that sex was not in the cards–I’d made it clear that I wouldn’t be hooking up with him. But kissing him was a different story, and my car was clearly not a good makeout spot.

So we did. We went back to his bachelor pad, which truly was a bachelor pad. Rock posters papered his walls. Laundry was strewn all over the floor and furniture. Dirty dishes were piled high in the sink. The dude was like a 49-year-old college student, and I’d just walked into his dorm room. Groovy.

We eventually found the couch under a pile of sheets, underwear and T-shirts, and that’s where we resumed our makeout sesh, which was pretty steamy–but I was leery of it getting too hot. So I stayed a bit guarded. He, however, didn’t.

Once things had ramped up to a certain point, I pulled away. “I think we better stop . . . this is not ending in sex tonight.”

“You’re right,” he agreed. “No sex. I get it. I respect that. But now you have me all worked up . . . ”

Ah, the guilt card–really? He was going to play the guilt card? The whole “you got me so horny, baby, that now you gotta have sex with me” card. 

But he didn’t. No, he didn’t play that card–he pulled a new one out of his back pocket that I’d never seen before.

“So, will you just sit there and let me look at you? While I . . . finish?”

Now, I’m all for being adventurous and trying new things or accommodating people–within reason. But this request threw me off balance. I’d never been asked that before. It seemed weird. But harmless. But really weird. But really–harmless.

I couldn’t find the words to respond, so I smiled politely, nodded, and sat there on his couch, scanning the room for something to focus on–because he’d already started finishing, and it didn’t seem right to get up, grab my purse and say thanks for a nice evening.

What does one look at when your date is jacking off? I’d never been faced with this question. He was looking at me but, at that moment, eye contact didn’t seem appropriate. And I didn’t want to stare (or even really glance) at where the action was. So for the next several minutes, I got fully acquainted with my date’s rock posters. They provided a nice distraction and focal point while I waited for, well, the climax of the evening.

Once Tom had gotten his necessary relief, he threw on some sweats and walked me down to my car. A quick kiss good night, an “I’ll call you tomorrow,” then I made a mad dash for home. By noon the next day I had sent about four texts, thanking him for the evening but explaining why I didn’t think things would work between us. Completely unnecessary, but I wanted to make sure this particular situation was shut down with a “Do Not Resuscitate” order.

I have no words of wisdom to share at this point–no lessons learned, no insightful takeaway. Nothing other than there are times when sitting on a new dude’s couch is nice . . . when you’re drinking wine, having interesting conversation, watching a movie or maybe kissing a little. And there are times when it’s just  awkward. Like when he’s spanking the monkey. Perhaps next time–if there ever is a next time–I will suggest that the monkey stay in his cage until I exit the bach pad.

There are just some things you shouldn’t accommodate for on a first date.

–Sienna