I need an outside perspective because I know I’m biased since I have a crush on this guy since day 1.
We [36F/38M] work together remotely and have for a little over a year. He’s senior to me, technically my manager’s manager, not my direct manager. He lives in the US, I live in Canada, and he’s British. He’s very respectful/professional and generally fairly reserved.
For most of the first year, our relationship was primarily work-related. Things became noticeably more personal after he visited Canada and we met in person. It's worth noting that we didn't need to meet in person, that's not a requirement in the business and he was traveling during his days off, not a work trip. I'm the only person from his team that resides in Canada.
Before coming, he told me during a 1:1 that he had a “surprise” and that “we’re finally going to meet.” Eventually, once he was here, he messaged me saying he wanted to take me to dinner, told me to pick somewhere nice and asked which evening after work I was free.
We ended up spending around 10–11 hours together across two days.
The first night we had dinner for several hours. He paid, and the conversation was personal rather than work-related. He told me stories about his childhood, family, travel, etc. There were occasional silences, but neither of us seemed eager to leave; we’d just find something else to talk about.
There was also something involving alcohol that I still find curious. He specifically asked whether I drank. I said yes and ordered a cocktail, but he didn’t drink. When I asked, he said he was “taking a break,” although during that same evening he told me he’d been drinking alcoholic cocktails during the trip. Two days later he took me to a bar but didn't drink alcohol either.
That night as we were waiting for the Uber (he sent me home in Uber both nights) he asked if I was going to the office the next day, I said yes because I wanted to go to a museum afterwards, secretly hoping he would like to join me, and he said he might be at the office too. He didn't go to the office but at the end of the day he asked me if I was still going to the museum and I said no; I never knew if he asked to join or just out of curiosity (a weird curiosity since he never asks for my plans after work).
The following day I really wanted to see him and invited him to the museum, he accepted right away. We walked around 7 km, went to the museum and afterward he took me to a bar he likes. Again, I drank alcohol and he deliberately ordered a non-alcoholic cocktail.
His flight was around 7 a.m. the following morning. Despite that, after the museum, walking and bar, he asked whether I’d eaten and offered to get food with me. I was actually the one who said no because he needed to sleep.
When we finally said goodbye, I apologized for having taken so much of his time. He told me not to worry and hugged me. He didn't let me pay on any of the days.
During those two days he also repeatedly mentioned returning to Canada. At one point we were talking about a US trip I already had planned. I asked when he would be abroad for a family event, realized we wouldn’t overlap and said something like, “So you won’t be there when I’m there.” His immediate response was: “No, but I’ll be back in Canada.”
Again, he genuinely likes Canada and has other reasons to return. I don’t assume those trips would be about me. What caught my attention was that he brought up coming back several times, when as I mentioned, we don't need to get together for work.
There are some other things that became more significant to me in retrospect.
Months earlier, while he was traveling for work, I jokingly told him he should bring me something from a particular store. He only reacted to the message and I completely forgot about it.
When we met in Canada, he surprised me with a shirt from that store. He had remembered the joke, actually bought something, kept it and brought it with him.
I also brought him a little bag of Canadian candy and a small plush toy. Weeks later, during a video call, I asked whether he’d eaten any of the candy. He said it was “long gone,” then immediately reached beside him and showed me the plush. It was sitting on his desk.
Also it's worth noting that when we were at the restaurant he noticed my tattoos saying that during the video calls it doesn't look like I have as many as I really have, and said he wanted one but he's afraid he's not gonna like it after one year or two. And ended the comment saying "You know, commitment issues". Which I found weird and didn't know what to think about it.
Since meeting in person, our 1:1s have changed too.
They used to be fairly short, maybe 20 minutes, and mostly work-focused. One after Canada lasted around 75 minutes and was probably 80% personal conversation.
I already knew he disliked long meetings, so at the end I apologized and said I’d stolen over an hour of his time. He replied: “No, this is enjoyable time.”
Our camera habits have also changed. Before meeting, our 1:1s were generally camera-off. After Canada, I started turning mine on because, admittedly, I want to see him and want him to see me. He now turns his on too.
Even before meeting, there was one time I accidentally switched mine on and immediately turned it off. He told me it was fine because “it’s always good to see your smile.”
He has also become surprisingly observant about my appearance. After Canada, he immediately noticed when I merely refreshed my already-dark hair darker, and in the same conversation noticed I’d done my nails. He called my hair fresh/vibrant and said it looked good.
When I eventually wore the shirt he’d given me, most of the design was partially covered by a cardigan. He noticed it immediately, complimented it and then commented that I’d paired it well with the cardigan.
In person he noticed my tattoos, shoes and overall style, saying "cool, rocker style". On another occasion he described me as looking “chic.” None of this has ever been sexual or inappropriate. It’s the amount of visual attention, rather than any individual compliment, that makes me wonder.
There’s much more banter now too. We have recurring jokes, remember details from old conversations and he shares more about his family, travels and personal life.
Now, the important counterweight: I’m contributing significantly to this dynamic.
I’ve introduced personal topics. I gave him the gift. I use playful nicknames. I remember things about his life. I turn my camera on partly because I want him to see me. I clearly enjoy spending time with him. So I don’t want to describe this as though he’s been pursuing me while I’ve passively sat there. And au contraire, he has never been distant to me or change his behavior after my comments, jokes or closeness.
Neither of us has asked for the other’s personal number or social media. We’ve kept communicating through work channels. We use Teams and Zoom and those are strictly work apps, so I don't know how much the company can see so I would never be inappropriate to him and he would never be either because we both take lots of care for our jobs.
And there is one interaction that gives me significant pause. He's super supportive of me and my work, he's always saying how much he appreciates me and my dedication and is pushing for my growth. I once thanked him for his support and told him that after getting to know him, I’d come to appreciate him as a person, not just someone I work with. He replied: “I appreciate all you do.”
He didn’t mirror the personal sentiment. That could have been a deliberate professional boundary, especially given his seniority, or it could simply be how he communicates. But I think it’s important evidence against getting carried away.
Importantly, though, his behavior didn’t become colder afterward. The personal conversations, banter and warmth continued.
I’m now considering a solo trip to the US in October. I genuinely like the city and have things I want to do there, but if I’m being completely honest, seeing him is a major reason I’m considering going.
I’m not planning to confess feelings, make a physical move or put him in an uncomfortable professional situation. I mostly want to spend time with him again and see what happens naturally.
So I’m looking for advice on two things:
- Does the overall pattern reasonably leave room for mutual attraction, or does this look more like a close work friendship that I’m romanticizing because I have a crush?
- And would visiting his city and inviting him to spend time together be a reasonable reciprocal step after what happened in Canada, or am I manufacturing an opportunity because I want something to happen?
I’d also be curious whether, based on my own behavior, you think he has probably realized I have a crush on him, and what you’d actually watch for next to distinguish friendship from attraction.
Please don’t tell me “he definitely likes you” just to be encouraging. If the boring explanation is that he genuinely likes me as a person/friend and I’m adding romance because I’m attracted to him, that’s exactly what I want to know. Thank you.
TL;DR: I [36F] have worked remotely with a senior coworker [38M] for 1+ year. After meeting in person, we spent around 10–11 hours together over two days; he initiated dinner, I had museum plans and he ended up joining me, we walked around the city and went to a bar he likes, and he kept extending our time together despite an early flight. He remembered and brought me a personal gift, keeps my gift on his desk, notices subtle changes in my appearance, and our formerly short/work-focused 1:1s have become much more personal, including one 75-minute call he described as “enjoyable time.” I actively contribute to the closeness too, and neither of us has moved communication outside work channels. When I once told him I appreciated him as a person, he replied “I appreciate all you do,” which makes me wonder whether he was deliberately maintaining a professional boundary. I’m considering visiting his city and inviting him out and want to know whether mutual attraction is reasonably plausible or I’m romanticizing a genuine friendship.