This is going to be a bit of a long explanation.
So I’ve been crushing on a coworker (F29) for a little while now and have been meaning to ask her out.
A different former coworker of mine who got fired a couple months ago (F31?) texts me a couple weeks ago asking if I want to grab coffee. Idk if she wanted this to be a date, a networking opportunity, or if she just wanted to catch up because she hadn’t seen me in a bit, but no matter what her intentions were I thought it would be nice to see her again so I accepted and decided to go into it with an open mind. However, the place we’re meeting tonight is more of a diner-style restaurant, so this appears to be a bit more formal than I was expecting and idk how I feel about that.
Around that same time, my work crush invites me to the CrossFit class she teaches. I have been going back and forth on whether or not I think she’s interested in me (in most situations with women I err on the side of “not interested”) just because of different interactions we’ve had sometimes leading me to think one thing and other interactions leading me to think another. She has been pretty upfront and straightforward with me about the whole CrossFit thing so it’s not like she’s trying to “trick” me into joining. I’ve been to a couple classes and I have genuinely liked them so far and because this is a cheaper CrossFit place I’m considering joining. It’s also a nonprofit organization that does a lot of good for the local community, which is why it’s cheaper. I know I probably sound like I’m totally getting played, but it’s not like she parades around work promoting her CrossFit class, and there aren’t many people at work she has expressed a strong desire to interact with outside of work. Just trust me it’s far from a sure thing that she’s interested in me but it’s definitely not out of the question.
Anyway, I’m definitely more interested in the current coworker (F29) than the former coworker (F31?), and I plan to ask her out soon, probably later this week, and I have a very creative date idea that is related to her interests.
But I’m worried about people at work finding out about this. My officemates were pretty friendly with the former coworker (F31?) so I don’t want them knowing anything if things don’t work out, and I definitely don’t want my current coworker (F29) to find out about the former coworker because I do not want to get a reputation as an office man-whore. I’m the kind of guy who likes to take things slow with women, and I don’t think I could ever date more than one person at the same time for more than like 2 dates because that would be my fucking nightmare. I work in a heavily female-dominated workplace and I have a good reputation among my coworkers. I just don’t want people to get the wrong impression of me, and I don’t want to hurt anyone or make anyone uncomfortable.
I’m very new to dating. I got my first girlfriend when I was 19 and we were together for 5-6 years and we started off as friends so I have never really dated before or “played the field”. I’m just nervous about how to navigate all this because I’m not sure I know what I’m doing.
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