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The original was posted on /r/tifu by /u/DrMrSirJr on 2026-03-01 23:01:59+00:00.
Tried to ask out my friend a little over a week ago.
Okay so this person is my friend but also my coworker (yes I know I’m dumb).
We’re not just strictly work-friends, we do hang out 1:1 outside of work about once a month (grab boba, grab coffee, go to museum, go to cat cafe, grab dinner, go to mall) and we text more days than we don’t. We’ve also had a lot of deep and personal conversations, and one time she came by my house at like 8 PM and stayed till 11 PM the night before work to vent cuz she had some family drama come up and needed to talk. So we def are past a purely work-relationship I would say. And also, it’s not really a long term career kind of job, it’s more of a seasonal gap-year kind of job. Mostly people that are in between undergrad and grad school or whatnot.
Anyways, two weeks ago at work, I asked if I could steal her for a couple minutes after work to talk to her about something. She said yes so after work as everyone left the office and went to their cars, we met up to chat.
All good, except my supervisor walked by right as I was getting ready to ask and started chit chatting about some work stuff and then left. Totally innocuous but it just threw me off my moment and made me all work mode and made it hard for me to loosen up and talk the way I wanted to.
I hadn’t fully decided if I was going to ask her out explicitly using the word “date” or test the waters by putting out feelers and see if she reciprocated. Was going to play by ear on vibes. But bc I had gotten thrown off by my supervisor, I ended up going the more roundabout way which I regret very much.
I usually prefer to just be direct as possible, but it’s been pointed out to me that for some friendships, sometimes making a big declaration and putting the other party on the spot to make an immediate binary decision can sometimes actually be more jeopardizing to the friendship. Sometimes it’s better to put out gentle feelers and taking their response to those as the answer. I suppose it depends on the person and the friendship. I thought I was being more “gentle” about expressing my interest but in hindsight I fully wish I had been more direct like my instinct.
So I asked her if she’d like to go with me to this local museum/botanical garden sometime in the near future. She said she was down. But I realized that it didn’t come across as a date, and instead came across as another normal 1:1 friends hangout. Cuz we already do that, so why wouldn’t she just think that’s what I meant?
So after I suggested the idea of the hang, and after she had agreed to it, I kind of realized I fumbled the ask, so I did say something along the lines of “It would be kind of a more special hang” and said the phrase “just the two of us”. When I mentioned that stuff, she did smile and didn’t rescind her interest in the hang.
Anyways, fast forward to next week at work. She had ghosted me the whole weekend on text and then at work on Monday, she was really cold and distant (wouldn’t look me in the eye and wouldn’t initiate conversation and gave short answers to everything).
Waited to see if she was having an off day or if it was because of me. Sure enough, it continued into Wed so on Wed, I finally asked to speak again after work.
She was pretty fired up and upset when we talked. Kind of laid into me.
Basically told me that I had made her uncomfortable, that she needed space, and that she’s now doubting the validity of our whole friendship. Uncomfortable because I crossed a line past friendship without talking to her first (hence the immense regret on not using the word “date” like I had thought about). And doubting the friendship, I think from what it sounds like, because she thinks the friendship was just one long con, which hurt my heart.
After she laid into me, she was basically going to just storm off. I was able to have her hear me out and explain myself and my intentions a bit. I explained that the friendship is the most important thing to me and how the friendship is very real to me and I apologized profusely for not being more direct and for making her uncomfortable. By the end of the conversation, she did give me a hug but yeah now I’m just giving her space (outside of work) and so I think it was big for me to be able to explain a bit and try to dispel some of her worries. But yeah not sure what’s going to happen to our friendship afterwards.
Ofc I feel so lousy and sick and sad that I’d make anyone uncomfortable, let alone someone I care about. I feel genuinely awful, and cried after the conversation just from thinking about making her uncomfortable. No ill intentions but the feeling it created was still the result.
And I’m just really sad that I likely jeopardized a friendship I consider to be a good one and a valuable one.
Not sure where things will go from here. Just giving her space in the meantime. At the very least, things are cordial enough at work again at least, so I’m glad we had the talk and I was able to clear up some things. But still, feels really bad.
TL;DR I expressed interest in my friend and coworker. Executed it poorly and possibly ruined the friendship.