Three nights ago, I went on a really good first date. Actually, I went on a great first date. The guy was fabulous on paper – attractive, successful, active, owned his own condo in Del Mar, a local San Diegan, and clearly quite smart. He’s the type of guy I have always thought I’d end up with.
And even better — he didn’t fall flat in real life. He was charismatic, funny, and quite chivalrous (paid, didn’t walk in front of me, drove me to my car, got out of his car to say goodnight…. etc).
But the best part of all… we really seemed like we were on the same page.
Both of us have done Match in the past, and both of us have jumped into “dating” after a great first date – only to realize that perhaps things should have gone a bit slower. So when this gentleman mentioned “taking it slow,” I was all for it! I readily agreed when he said that he thought the best relationships started out as friendships and he agreed with my many thoughts on our generation’s dating style. After much discussion, I felt great and I interpreted our conversation to mean that we were both interested in exploring where this could go, but weren’t going to do anything in a rush.
At the end of the night, I went for the hug. This seemed appropriate seeing as how we had just discussed taking it slow. Besides, I was pretty sure he was interested in me and I didn’t need to make out in a parking lot for confirmation.
Later that night he texted me good night and I thought, Neat! Still on track. Then the next day, he texted me again and I thought, Ok, cool. He’s definitely interested. I can’t imagine this guy is just THAT pumped to have a new female friend.
So we text back and forth for a while and eventually he asks me to come over to his house and hang out and have wine. Since he only lives a block away I figured, sure, why not. He also told me I could invite the roomie along; which didn’t weird me out because we’d talked a bit about our roomies and I had told him how both of us were new to the area and wanted to make Del Mar friends. Plus, since he and I discussed taking it slow, I decided it would make sense for me to bring her along.
Well, somewhere along the way, I must have gone wrong…
We show up and he gives us the tour (great house) and then we settle down on the couch. Now, I may have blown it a little in my choice of seating. I sat at the far end of the couch, my roomie sat in the middle, and he was left sitting as far away as possible from me. But still, I don’t think seating can be entirely to blame for what happened next.
His roomie came down and we were all just sort of hanging out, like the way I’d hang out with my guy friends. Just kind of talking shit and doing nothing – all of which was fine until somehow the conversation turned to rim jobs and anal sex. No, I am not making this shit up. Here we are, just hanging out, drinking wine and somehow, all of a sudden, I am being asked if I have ever taken it up the butt. And by a guy who had taken me on a lovely date the evening before!
Um, what the fuck is my response supposed to be to that?! This isn’t something I even talk about with my best girlfriends… it is certainly not something I am dying to divulge to a stranger. And as I am trying to figure out how best to respond to this awkward conversation, the cute guy decides to tell his own ass story. Let’s just say it involved shit – which no matter how you spin it, isn’t the least bit romantic.
I kinda just became silent. How did we get here? What did I do that gave him the impression that I wanted to be one of the bros. Taking it slow was a great plan. But there should be some rules about just how “friendly” you get if you are still ultimately hoping for the possibility of a relationship one day.
Pretty shortly after this talk, I decided it was time to go. I probably wasn’t super nice, because let’s be real, I was in shock. So I gave the guy a hug, went home, and bitched about the evening for like 30 mins. After I calmed myself, I realized perhaps I could have been a bit less of an ice queen because in all fairness I am sure I am partly to blame for what happened. So in attempt to not appear to be an uptight, prissy bitch, I just sent him a quick text that said – “Thanks for the wine and the hospitality.” He responded right away and said, “Absolutely. You’re welcome anyime. Sorry about the butthole talk at the end there. I hope it didn’t make you feel awkward.”
I got that and thought, Huh, so you knew it was weird too…
After thinking about it, I think we have three possible scenarios going in here.
1. He isn’t interested in dating me. Plain and simple. He hasn’t kissed me and he’s asked me if I’ve taken it up the ass… sooo not exactly indicating romantic interest.
2. He is interested in dating me but he just got a little drunk and caught up in the bro moment. His roomie is clearly a bro (albeit a nice one) and my roomie and I are casual people. I could see how he might have just been in the moment and lost track of what is appropriate and what’s not.
And 3. He is interested in dating me but isn’t sure I am interested and so he is confused. If I look at my behaviors I have been nothing but platonic towards him, so perhaps he just figures I’m not into it.
Well whatever the case, the night provided me with some much needed learnings. Clearly I should have defined for myself the difference between taking it slow and taking it nowhere. For future reference, here are some guidelines for keeping it platonic without killing the chance of a romantic future.
- Flirt – Make it super obvious that you find the other person attractive. Touching, eye contact, etc, all OK. Sitting across the room and giving weak hugs, not super clear.
- Communicate openly – Our initial conversation about wanting to take it slow left me feeling great. I felt like we were having an open dialogue and I felt clear on the takeaway and the direction.
- Don’t enter a purely “friend” hang out sesh, right away - I set myself up for failure when I agreed to hang out on a Tues, in my sweats, with our roommates, at his house. If I had been smart, I would have declined that particular offer and waited for a more date-esque invite.
- Avoid drinking - If you are attempting to strike the balance between taking it slow and friendship, put down the glass. It’s a hard enough to play this right when you are cold sober. Add in a few gasses of wine, and things get confusing, fast.
- Speak up if something heads in the wrong direction – I really should have just stopped that conversation before we got to the multiple shit stories. I should have just said, “Uh uh, we are ladies and I don’t think it is appropriate to talk about this.”
In the end, I am actually a little sad that I had to learn this lesson on a good guy. I actually think we could fit well together, but I am afraid I may not have played my cards right. I haven’t given up hope though, that we may be able to get back on course because I did hear from him again last night.
Regardless, dwelling on the situation would just be depressing, so I’m not. Instead, I am going to think about how much fun I had out last night, rocking my amazing new Dylan George leather pants, and having conversations about things other than butts, asses, assholes, or anal beads. Now THAT is something to be thankful for. Happy Turkey day, y’all!