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I would like your advice on a situation. I’m 35-year-old gay man. Last year, I dated a 22-year-old for six months. We broke up because of communication difficulties. He also violated my trust. We’ve remained friendly since then. I still have lingering feelings for him. I don’t know if I want to date him again, but I’d like to be sexually intimate again if possible. He identifies as poly and is very into casual sex, but is also very awkward and anxious—he often struggles with telling people what he wants. Casual sex seems to be his comfort zone.

When we had dinner last week, I leveled with him. I said, “I still have unresolved feelings for you, though I’m working through them. If you’d like to do something outside of friendship, we can talk about it some time. I’m also very happy with us remaining friends.” His response, “That’s something to think about.” Then he talked about guys he was fucking. And we had casual banter about our history together.

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After dinner, We went back to his place to watch some TV. It was humid so he took of his pants. He said, “Well, you’ve seen me naked before,” and then he sat down next to me on the couch. I took of my pants, too.

It was then awkward for the next thirty minutes. He made no moves but also didn’t react to any moves I made—like putting my arms next to his and pushing in gently. Nor did he run away. I also wasn’t particularly assertive. I'm usually fine taking the lead, but it’s hard with my ex: he is nervous and passive. His body language when he’s turned on is similar to that when he is uncomfortable. I wanted a clear "yes" from him before I proceeded.

He tells me that he needs to sleep. I get up to leave, we make prolonged eye contact. I can’t tell what he wants, so I ask: “Do you want me to kiss you or not?” He says: “Well, you want to kiss me.” I say: “I know what I want. What I want to know is what you want, because I don’t want to break any barriers with you.” He then gets visibly upset and then says: “I’m not a broken person!”

I say: “I never said you were!”

He says: “You can do it.”

I hesitated... because... well, he's still upset and I didn’t expect him to get pissed.

I say: “Are you sure?”

He repeats: “You can do it.”

I go in and we have an extremely weird kiss. It is two pecks on lips, no tongue. He seems tense. I am deeply confused. We hug, and say our good-byes. We’ve texted a bit since then, but haven’t discussed the night. I tend to believe he isn’t interested. If that’s the case, I’d like a clear indicator, so I let these feelings die. When we’ve had conversations about feelings in the past, he’s practically imploded. Should I let this shit go? Am I being a creepster? It it worth trying to salvage a friendship?

Dummy Is Needing Knowledge

You shouldn't have done it.

You shouldn't have kissed your ex—even after he removed his pants, even after he allowed you to remove your own, and even especially after he didn't "react to [your] moves" and refused to answer a direct question about whether or not he wanted to kiss you. I'd like to think this is obvious to you now, DINK, now that you've got your pants on and your dick isn't taking every one of ex's ambiguous and/or mixed and/or negative signals and rounding them up to, "He just wants me to take the lead!"

But I'm worried that it might not be obvious to you, DINK, so I'm going to break it down. When you said...

I still have unresolved feelings for you, though I’m working through them. If you’d like to do something outside of friendship, we can talk about it some time. I’m also very happy with us remaining friends.

...your ex didn't say, "Oh, you wanna be fuckbuddies? Great, I'd be down." And the reason he didn't say that, DINK, is because I don't think he heard you say what you seem to think you thought you said. (That sentence hurt me as much to write as it did for you to read.) Here's what went down...

You said: "I still have unresolved feelings for you, though I'm working through them."

He heard: "Part of me still wants to date you or fuck you but I'm working at getting over you because I don't really want to date or fuck you."

You said: "If you'd like to do something outside of friendship, we can talk about it sometime."

He heard: "But, hey, maybe you want to fuck me. I'm not ready for that and it may not be something I'll ever want but check back with me later and maybe we can talk about the possibility of someday the two of us fucking around or possibly even dating again. If that's what you want. I don't. But we'll see how I feel later."

You said: "I’m also very happy with us remaining friends."

He heard: "Let's just be friends."

If your ex heard it like that—and he most likely did—that would explain why he didn't respond to your pantsless nudging on the couch. He was sitting there thinking, "This is weird—earlier tonight he said he only wanted to be friends and now he's sitting here without any pants on and nudging my leg." It would also explain why he was flummoxed by that prolonged eye contact and it would explain his defensive reaction to your bizarrely confrontational question. ("Do you want me to kiss you or not?") In other words, DINK, your ex wasn't confusing. He was confused—and it was your mixed/ambiguous/contradictory messages that confused him.

You didn't make it clear that you wanted to fuck around. You may have wanted to tell him you'd like to be friends-with-benefits and you may have thought you were being clear, DINK, but what you said was far likelier to heard as, "I'm still attracted to you sexually and that's a problem because I only want to be friends," particularly if (as seems likely) you were the one that ended his relationship. And you didn't make yourself clear for the exact same reason millions of other people have failed and will fail to make themselves clear in similar circumstances: you phrased the ask ambiguously so that you could deny having made the ask if his answer was "no." It's a trap that insecurity and ego sets for us; when we make ourselves vulnerable and open ourselves up for rejection our so-easily-bruised-they're-basically-bruised-in-advance egos take over and build an escape hatch into the ask.

Anyway, DINK, the next time you ask someone if they want you to kiss them and instead of answering the question in the affirmative—the enthusiastic affirmative (best standard for consent and practically a tense at this point)—they repeat "you can do it" again and again and they appear to be so upset that you feel obliged to ask them if they're sure... yeah... going in for that kiss is only going to make a weird situation weirder. As you experienced.

And finally...

I tend to believe he isn’t interested. If that’s the case, I’d like a clear indicator, so I let these feelings die.

You already have your indicator, DINK. Shit was was weird, shit got weirder. Don't just sit there waiting for those feelings to die. Kill them.


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