@Kate lol ok. Sure, it was fun talking to him but I sincerely doubt anything will ever happen and that’s fine. This is not the first work crush I’ve had. ?

@Fyodor It’s not really obvious to me because if he were interested wouldn’t he…ask me out? I’ve joked around about dating and how I’m single. It was a little awkward because I’d scheduled our meeting for half an hour but it ended up being an hour because we just kept chatting. I actually ended it because I had to go to another meeting.

(Also, for context, almost everyone at work asks me when I’m performing next so I didn’t think it signified particular interest from him.)

I’m so petrified of doing anything that would seem in any way unprofessional that I don’t think I’d ever make the first move. I figured I would just keep working with him and if he comes to my show, that’s awesome and we can talk more there…I guess?

First. Ver, the meeting the parents… exciting! I’m glad it went well. That’s so fun.

As far as dating a coworker goes… I can’t tell you if he’s interested but I do know that it takes a lot longer to make a move. I’ve had a lot of experience dating (and being twice engaged and once married) to a coworker. If the person cares about his or her job, they tread a lot more carefully.

Another example, my cousin married an ex-coworker. They were in different departments but he waited til he left the company to ask her out. I think they went on a date within a week of him leaving. They were both very interested prior.

So again, I don’t know if he’s interested. But him not asking you out isn’t really a indicator. Most work relationships are easier to start if you do group happy hours or outings where you get to know someone outside of the office.

I would never enter a co-worker’s comedy show in my calendar just to be nice! I’d be like, “Yep, sounds great, I’ll see if I can make it” or something vague to be nice. (I did this at my last company for a co-worker who invited me to her comedy show. I liked her enough, but not enough to go to her show.) At a minimum, he sounds interested in getting to know you better, so for now, maybe take out the potential for romance out of the equation?

I think when you meet someone IRL, things move slower, generally-speaking, because I think people are inclined to get to know one another a bit in lower pressure situations before asking the other out on a date. Online dating is nice in the sense that it’s a pool of people who are single and looking, but you start on a different page with people you meet than those you meet IRL.

@Kate, I totally get what you’re saying and I will be careful! For context about this presentation – my manager, the SVP of sales, was trying to book me and several other comics for an actual show in the evening for our big dinner after the day-long meeting, but it ended up falling through as a result of not being able to find a room big enough. This is basically a way to incorporate a bit of myself into my presentation rather than try out jokes. I am not planning to do any “real” standup, but all company-related jokes – like poking fun at the conference rooms, the tons of acronyms, etc. Trust me, I know how to hone my content! It’s not “real” standup in that it would make zero sense to anyone outside of the company, but inside the company everyone will [hopefully] think it’s hilarious.

And also – I already cleared it with the SVP that I’ll start my presentation with a little bit of company-centered comedy, and he loves the idea. 🙂 There will be no “edgy” material, for sure.

I went on a first date this weekend, the first date I’d been on in a a couple of months. (I recently decided to date with intention; i.e. not waste time on guys that I know are definitely not relationship potential.) This guy seemed promising, but the date was very blaaaah on my end. There was nothing really wrong with him or the date. I just didn’t feel any chemistry, did not feel compelled to kiss him. He apparently did not feel the same and has already been hitting me up to go out a second time. Should I even bother? I know chemistry can sometimes develop over time, and that’s happened to me before. But I’ve also been on dates where I feel like I know within the first 5 minutes that he isn’t the one. I’ve been single for over three years now while working through some health issues, family issues, career issues, etc. Now things have settled down, and it seems like the right time to get back into seriously dating, but it just feels so tedious and unsatisfying. Maybe I just need a pep talk