|I know the general advice is to never date your co-workers, but I really like one of mine and am having some intense carpe diem/what's the worst that could happen feelings. Help me figure out if asking him out is worth it. Snowflakes below.
-"Sam" and I are semi-regular collaborators at our workplace, but are not in the same department and do not have the same manager. Our titles and the structure of our employer are such that there is basically no scenario where we would ever be under the same boss, or end up with one of us reporting to the other. He works entirely on-site, I am mostly remote but come into the office periodically.
-We are close in age and both unambiguously single.
-We've been meeting up after work for drinks periodically since last summer, which is something he first initiated. It doesn't feel especially flirty, we mostly end up talking about work, but the conversation is easy and fun and idk, I'm bad at reading vibes. He has been back to my house briefly after some of these meetups and gets along famously with my cat.
-Neither of us is making immediate plans to leave our employer anytime soon. I suspect I'd leave before he did, but even still, we're probably looking at months or years before we're no longer co-workers.
-I get why the advice not to date your co-workers exists. On one hand, I get that it might make my life awkward if it turns out he's not interested, or if we did date and things blew up. On the other hand, I feel no deep loyalty to my employer, fascism and climate change are coming for us all, and someone I know just died suddenly this week. My mood is overwhelmingly one of, I only have this one short wild and precious life, shoot your shot.
Am I underestimating the worst that could happen? Are there other complications I'm not thinking through? Please talk me down from doing something impulsive and regrettable or offer your words of encouragement, I am open to either.