u/Glenncoco23

I (26M) met someone (21, transmasculine/he-they) who works at a coffee shop next to one of my construction jobs. Sometimes I stop in there for coffee or something to drink before heading back to work. We started off with some banter and small talk, and things were going really well.

The shop does this “after dark” event at night, and one Friday I decided to show up. The entire night, he basically stayed near me the whole time whenever he wasn’t busy. At the end of the night I walked him home. I’m usually cautious physically because I never want to make someone uncomfortable, so I normally go for a fist bump instead of assuming hugs are okay. Instead, he ignored the fist bump and went in for a hug.

I walked home excited as hell.

We kept talking more and more after that. Eventually I got his Instagram, and by the second Friday I noticed I had been added to his Close Friends story. The first thing on it was him promoting the next “after dark” night at the coffee shop.

When I showed up and mentioned I saw I got added to Close Friends, he smiled and said, “Yeah, I was hoping you’d notice that.” In my head I was screaming. I thought things were genuinely going really well. That night I walked him home again, and afterward we started texting constantly.

The next day I was at a pool hall and he replied to my story asking where I was. I told him, if he wants to come play pool, and even offered to pick him up. He said he was at work, but the second he got off he came straight over. We ended up hanging out from around 7 PM until midnight just talking and playing pool.

This was also the night I found out he used he/they pronouns. Before that, I had been using she/her because I genuinely did not know. Once I found out, I corrected myself immediately because I didn’t want him to feel uncomfortable or invalidated.

Before he left, I asked when he was free again because I wanted to hang out more. We talked about Dave & Buster’s and Texas Roadhouse, and he immediately said he was free Tuesday. Which I mean, I took that as me asking him out on a date.

At this point we were texting constantly every day. Not just casual texting either. Long conversations, stories about work, random life stuff, sending pictures back and forth, everything.

Sunday came around and he invited me to come see him while he was working at another coffee shop. I couldn’t make it in time, so he said he was going to Barnes & Noble afterward instead. Once I got off work, I texted him asking if he still wanted to go, and he immediately said yes.

We spent hours at Barnes & Noble just talking while he worked on his own stuff and I read a book. Then we went to dinner afterward and kept talking for hours more. At one point we just sat in my car talking late into the night.

This was also where things started feeling more emotionally intimate to me. We started talking about past relationships, sex, experiences, personal stuff, etc. I don’t normally talk about those things with people unless I feel genuinely comfortable around them, so it made me feel closer to him.

At this point we had hung out three days in a row.

Monday I intentionally tried to give him space because I didn’t want to seem suffocating or clingy, but he still kept texting me throughout the day. Then he invited me to go dumpster diving with him during his college move-out because people were throwing away good furniture and random stuff.

I enthusiastically agreed because honestly that sounded fun to me. During all of this he had also started calling me “pookie,” which absolutely did not help my confusion about whether this was platonic or romantic. Because I get it some people have pet names for their friends and I don’t know if that was what he was going for.

I’m very direct when I like somebody romantically, but I also don’t assume things easily. Even after all this, I still kept wondering if he was just extremely friendly.

At one point I showed him food I was cooking for lunch, and he said it looked really good. I joked that I’d cook for him one day, and he immediately said he loved baking and would bring dessert if I cooked. So I started planning out a dinner idea and asking about allergies, foods he liked, foods he didn’t like, etc. Throughout all of this, I had also been paying when we went out because I was usually the one inviting him places.

Then Thursday happened.

He told me he was going to Miku Expo, and I misunderstood “expo” at first and thought it was more convention-like. I put together a little care package with things I personally would want if I was going to something crowded all day.

Some protein shake in case you get hungry, painkillers, a little sewing kit, a lint roller, hand sanitizer, eyelash glue. Just practical stuff.

I dropped it off at his work. Like three hours later he texted me asking how much it cost and said I didnt have to do that. I told him it was genuinely no big deal and that it was just stuff I personally would want if I was going to a convention myself.

Then a few hours later he texted me:
“I hope I wasn’t leading you on. I’m not really looking for a relationship right now.”

NGL, that hurt a little.

I told him the thought had crossed my mind, but I genuinely didn’t know whether he was interested romantically or just very friendly. I also told him I’m personally looking for a serious relationship if I really like somebody, but I don’t assume romantic intent unless someone clearly says it.

Then he clarified that he actually DOES want a serious relationship eventually, but only with somebody who genuinely sees him as a man because his last situationship made him feel invalidated.

I told him I completely understood why that would matter and that I would never want him to feel invalidated as a person.

The thing is, I genuinely liked HIM. I wasn’t secretly viewing him as a woman the whole time. I liked his personality, humor, communication style, interests, energy, all of it.

After that conversation, though, everything changed.

We went from texting constantly every single day to feeling like I’m talking to a brick wall. Responses slowed down dramatically, conversations became shorter, and now I feel hyper-aware every time I text him because I don’t want to make him uncomfortable or seem clingy.

At the same time, I also don’t want to suddenly become distant because I don’t want him thinking my feelings toward him changed after learning he was transmasculine.

I genuinely still want to be friends because I really enjoy being around him, but now I honestly have no idea how I’m supposed to navigate this situation naturally anymore.

I like him as a person as we share a lot of similar interests. And even with no romantic intentions, I would like to keep him around because he seems genuinely like a fucking awesome person. So if I keep inviting him out, do I seem clingy? And on that same note if I give him some space, does it look like I was only interested in him in a romantic way?

Did I come on too strong without realizing it? Did he actually like me and panic once things became emotionally serious? Or was I genuinely just misreading a very friendly person this entire time?

TLDR: I (26M) became extremely close with a transmasculine friend (21FtM) over a few weeks through constant texting, hanging out multiple days in a row, emotional conversations, pet names, and what felt like mutual chemistry. After I gave him a thoughtful care package for Miku Expo, he told me he hoped he “wasn’t leading me on” and said he wasn’t looking for a relationship right now, although he later clarified he DOES want a serious relationship someday with someone who truly sees him as a man. Now communication feels distant and awkward, and I don’t know if I came on too strong or how to continue the friendship naturally.

I (26M) met someone (21, transmasculine/he-they) at a coffee shop next to one of my construction jobs, and I genuinely cannot tell if I completely misread the situation or if things just became emotionally complicated very quickly.

For the sake of the story, I’ll call him Billy.

I started going into this coffee shop during work and we immediately clicked. We talked constantly every time I came in. Eventually I found out they did this “coffee shop after dark” thing where the place stays open late at night, so I showed up.

The first night I went, it was basically just me and him talking for hours whenever he wasn’t working. At the end of the night I was getting ready to leave and he went, “No, don’t leave yet, help me close up.” So I stayed and helped clean the place up.

Afterward I walked him home. I’m usually cautious physically because I never want to make someone uncomfortable, so I normally go for a fist bump instead of assuming hugs are okay. He ignored the fist bump and went in for the hug himself.

I walked home feeling pretty excited about the whole thing.

Over the next week we kept talking more and more. Then the next Friday came around and I stayed for another after-dark night. Before I went, I noticed I had been added to his Close Friends story on Instagram. When I showed up and asked about it, he said, “I was hoping you would notice that.”

At that point I started thinking there might actually be mutual interest.

I was trying to play games with another customer there, but realistically I was there to see him. I walked him home again afterward.

The next day he replied to my Instagram story while I was at a pool hall and asked where I was. I told him, and he said he didn’t know how to play pool. I jokingly offered to teach him and he showed up way faster than I expected.

We hung out for hours. At the end of the night he was showing me his car, talking about random stuff he bought that day, life in general, etc. Before leaving I asked when he was free again because I wanted to hang out more. He immediately said Tuesday and got excited when I suggested Dave & Buster’s and Texas Roadhouse.

During all this I found out he was transmasculine and used he/they pronouns. Genuinely didn’t bother me. I liked the person, not the label. Before then I had been using she/her pronouns because I genuinely didn’t know, and once I found out I switched immediately. I even asked why he never corrected me earlier, because it wouldn’t have bothered me at all to use the correct pronouns.

Sunday we hung out again for around 5-6 hours between Barnes & Noble, Applebee’s, and then sitting in my car talking afterward.

Monday he invited me dumpster diving during a college move-out because he found cool furniture. I enthusiastically agreed because I actually enjoy dumpster diving. I met one of his friends and later met his parents briefly when we dropped stuff off at home.

Somewhere during all this we also talked about me cooking dinner for him while he brought dessert.

At this point I honestly thought things were going really well.

Then Thursday happened.

He was going to Miku Expo, so I made him a little care package with things I’d personally want at a crowded convention. Stuff like sanitizer, painkillers, a sewing kit, snacks, etc. Nothing insanely expensive, just thoughtful.

A few hours later he texted me saying, “I hope I wasn’t leading you on. I’m not really looking for a relationship.”

That completely blindsided me.

I told him honestly that yes, the thought had crossed my mind, but that if I pursue someone romantically I’m usually direct about it. I don’t really play games or assume things. I also explained that I’m personally looking for a serious relationship when I genuinely like somebody, but that I’m also naturally very friendly with people in general.

Then he clarified and said he DOES want a serious relationship eventually, but only with someone who truly sees him as a man because his last situationship made him feel invalidated.

Honestly, I completely understand why that would matter to him, and I would never want him to feel invalidated by me.

But I genuinely liked HIM. I wasn’t secretly viewing him as a woman the entire time. I liked his personality, humor, interests, communication style, energy, all of it. I thought we had chemistry.

Now granted, it has only been about four or five days since that conversation, but we went from texting constantly every day, sending photos back and forth, making plans naturally, etc., to barely talking compared to before. That sudden shift has made me nervous that I accidentally made things uncomfortable.

I talked to a few friends about this, including some of my women friends, and some of them think the “I’m not looking for a relationship” followed immediately by “I do want a serious relationship, but only with someone who genuinely sees me as a man” sounds emotionally more complicated than a flat rejection. Others think he was probably just trying to establish boundaries before things escalated further.

Either way, I told him I was still completely okay being friends because I genuinely enjoy being around him, and he said he was okay with still being friends too.

The problem is that now I genuinely do not know how to navigate this without making things worse.

I still want to invite him places because I enjoy his company, but I don’t want to overwhelm him or make him uncomfortable. At the same time, I don’t want to suddenly become distant either, because I worry that could accidentally reinforce the idea that my interest in him changed after learning he was transmasculine. Or that I am somebody who is trying to establish a friendship just to eventually date and now that that was rejected I don’t wanna be friends with them, which is definitely not the case.

For people who have been in situations like this before, how do you continue the friendship naturally after a conversation like this without either becoming emotionally overbearing or pulling away so hard that the friendship dies entirely?

TL;DR: I [26M] became close with a transmasculine friend [21FtM] very quickly and started developing feelings because our interactions felt personal and intentional. After I made him a thoughtful gift, he told me he hoped he “wasn’t leading me on” and clarified that he only wants a serious relationship with someone who truly sees him as a man. I reassured him that I respected that and still wanted to be friends, but now communication feels noticeably different and I don’t know how to continue the friendship naturally without making things uncomfortable.

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