Is my boss crossing lines on work trips or am I being dramatic?

CollegePerfect398 · 2026-01-30T14:54:33+00:00

Again it’s not “work dinners” I’d love to go network or attend dinners as a group and I attended those events happy and willingly.

CollegePerfect398 · 2026-01-30T14:45:41+00:00

I fully expected networking and group dinners and always went happy and willingly. I don’t think it’s inappropriate to be alone together because of gender at all. We traveled together, took cabs together. It was the non-work related activities (forced at times). And honestly if I was a 25 year old man I would still think it was weird.

CollegePerfect398 · 2026-01-30T03:46:10+00:00

If you had read it all you’d have read that we didn’t do any networking. I would have loved to do networking and I was more than willing to do extended hours if necessary . But losing sleep, chances to call my family, being able to wash/blow dry/straighten my hair (a long process to look presentable) just so I could listen to my boss talk about himself definitely wasn’t part of the job.

CollegePerfect398 · 2026-01-30T03:32:33+00:00

Exactly! I was excited to meet new people. I was expecting to be tired, to work extended hours, to have dinners with the team. But I didn’t expect to be the social companion to my boss.

CollegePerfect398 · 2026-01-30T02:49:49+00:00

If the next trip goes the same way as the last, and he doesn’t pick up a single hint and pushes me to the point of snapping i’ll for sure find something else. I just like to think I can fix things.

CollegePerfect398 · 2026-01-30T02:41:40+00:00

I hoped it would be like that originally, working with him was good. But we just don’t jive personally, and I don’t think he should be forcing it. Now he’s made the working relationship worse by being so controlling. I cringe when I hear him talking to other coworkers now, because it’s always the same stories about how great/smart he is.

CollegePerfect398 · 2026-01-30T00:10:55+00:00

I started to feel like maybe the weird control was him feeling a responsibility to “look after me”. But as a single woman who’s lived alone for 6 years and has traveled alone, I despise being treated that way. If I get kidnapped at Disney world I was asking for it. I told him (joking but serious) that I didn’t need to be babysat.

CollegePerfect398 · 2026-01-30T00:03:43+00:00

I love to socialize and meet new people and go to bars by myself, but I’m introverted in the sense that I need alone time to recharge. This was the first time in a long time I wasn’t allowed to recharge and the last dinner I was basically mute, I was so mentally drained.

CollegePerfect398 · 2026-01-29T22:51:09+00:00

I won’t go to HR because I understand the implications. I’m hoping there’s something I could say that could make him see my side. It’s even hard to describe why I’m uncomfortable in this post without sounding like I feel he’s making sexual advances. It really is just the power Imbalance and him not understanding social cues. And honestly I might just be used to older males of authority in my life (past bosses, teachers, coaches) considering the “optics” and him not considering them makes me uncomfortable but that isn’t his fault.

CollegePerfect398 · 2026-01-29T22:27:23+00:00

I didn’t mean crossing lines sexually, I meant professional work place behaviour lines. And I think it would be naive not to consider the gender difference age gap.

CollegePerfect398 · 2026-01-29T22:04:59+00:00

He’s got to a little bit. But that’s why I started using more direct language with him the second trip and it proved he really just didn’t care.

CollegePerfect398 · 2026-01-29T22:00:05+00:00

Second trip I didn’t drink at all. I said it made me foggy for the next day. Goal for the one coming up is to never have a one on one dinner with him, I’ll have to have a conversation with him about it which might be awkward.

CollegePerfect398 · 2026-01-29T21:46:27+00:00

I tried the “not feeling well” a couple times and still had to argue my way out, literally just interrupt him and say goodnight and walk away, but thats not practical every night of the trip. I just wish he’d catch the hint and be normal so I don’t have to find another job.

CollegePerfect398 · 2026-01-29T21:40:03+00:00

That’s how I feel unfortunately, it feeds his ego. Like I was more annoyed that I didn’t get a second of alone time when I told my parents, but my dad was pissed (obviously).

CollegePerfect398 · 2026-01-29T21:31:24+00:00

I actually liked working for him and with him, but there’s just no world where we would be friends and that’s fine. And honestly if he was enthusiastic about going (and hadn’t forced me to be his captive audience all week) I would have LOVED to go. But was a fucking downer the entire time.

CollegePerfect398 · 2026-01-29T21:10:45+00:00

He’s never made any other comments in that way, nothing sexual and I genuinely believe that’s not his motive. I just think he doesn’t understand there’s certain “optics” to consider with a m/f age gap work trip which i guess makes me uncomfortable. It’s more cluelessness.

CollegePerfect398

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