We Tried Again and Failed. Now What?

I was apprehensive. You were too. But you said it was chill, that we could meet up casually, and I decided to trust you. I feel guilty now, as if I should have known better. For us both.

We met at bar in between our places. It was a nice setting. I sat on a comfortable couch, waiting for you. Watching you walk through the door, it was surreal. Like a time machine back to last year. We hugged and it felt good. We smiled. I had a beer and you had wine, then another. I switched to whiskey.

At some point we ran out of things to talk about. I guess we were each thinking of something else… So we addressed it: Should we have sex? First we danced around it, but then I just said, when you asked what I was thinking: “I’m thinking about putting my dick in you.” It was the truth. And I liked how we could be so direct. Maybe it wasn’t the most romantic thing, but still, it was something that we were perhaps craving.

We went back to my place and it felt great. Just like old times, of course. Neither of us knew where it would lead, but I made sure to suggest that it wouldn’t go anywhere serious. You seemed okay with this. You thought we could maybe work out a friends-with-benefits situation. I thought even that was getting ahead of ourselves. I should have known then.

You left in the middle of the night and didn’t even expect another call. I waited a week. I was also wondering if perhaps you would get in touch with me. I had a feeling you wanted to, that this whole re-connection was your idea, and that you should take the lead, but of course you wanted to feel wanted, for me to instigate. So I messaged you and you were happy.

Now, I had told you: I’d been seeing other people. You said you knew it, that you didn’t care. Or maybe you just didn’t want to care. I cancelled some other plans so that we could meet up on the day you were most free, and those other plans were a bit on my mind. I suppose it was here that things really went awry: talking with you about how frantic my mind was, how I felt like everyone wanted to see me at once.

All you heard was that I had options, that you were just one girl of many. It’s really not like that, at least from my perspective, as a guy. But in a literal sense, it was true. I didn’t see all these others as actual “options” in terms of a girlfriend or anything, but I suppose we all have options in regard to what to do with our evenings.

It was my mistake to think I could talk so candidly with you about this stuff. I don’t know why I brought it up. I mean, it was on my mind, and we want to be friends. I feel so relaxed with you, it’s natural for me to bring up anything I’m thinking about. And in your head, this sounds good – you want me to say whatever I’m thinking.

But suddenly, you were practically crying. In the restaurant. You were drinking lots of wine, which surely didn’t help, or maybe it did. Who knows.

Somehow we got through it and you came over afterward. We had sex. We started to watch our show on Netflix. And then you started crying again. Everything flooded back in. You were devastated. You wanted all of it back, the whole relationship. The friends-with-benefit arrangement was a Trojan horse – of course you wanted more.

You wanted me to tell you exactly why not, to specifically say what was so wrong with you that makes me unable to commit. Why couldn’t we just get back together? You demanded knowing. Such a terrible spot to be in as a (former) lover. I didn’t know what to say. Of course not. I wanted to just give you a hug, let you cry, and then I started to cry too, overwhelmed with the painful injustice of love and mismatched feelings. I pitied you and myself for being the bad guy in this. I just didn’t want you to run out in the middle of this, like last time.

We were super-sad for like an hour. It wasn’t fun. Like breaking up, all over again. Why do people do this?? It’s so hard. I should have known better, but I wanted to believe… that you were somehow over it, ready to be friends, or just hook up casually. I feel so selfish, so greedy, thinking that this was possible. And so foolish. I’m sorry. But trying is what you wanted. Why would I say no? How could I? Well, now I see how…

The last time we had sex really did feel like a finale, a culmination. Our tears had abated. We channeled our remaining emotions into the act, had a cathartic experience. Then we fell asleep next to each other once more. And you sneaked out in the middle of the night again, for the last time I guess.