I recently found out that my crush at workplace is highly likely, like me, in the closet himself. We are not close; at best, we are acquaintances who have no reason or chance to interact much apart from the occasional hellos in the hallway. There were times when I thought he might be curious about me, from the way he looked at me, but there were also times when he would look so cold, almost angry, whenever we crossed paths. My question is: how could I approach him to extend a tentative hand of friendship? I would quite like to hang out with him, but I also suppose it would be awkward to suddenly ask him to go for a meal or something (we have no mutual friends we hang out with). My plan is to write him an anonymous email, expressing my admiration for him. I will not mention that I have reasons to believe he is gay, but will say that I am trying to find a closure to my long-standing crush on him. Any advice?
I think an anonymous email 'expressing admiration' is a terrible idea: 1) It's not 'extending a tentative hand of friendship' because he won't even know it's from you, so won't achieve your stated aim. 2) It's not appropriate in a workplace environment. If I got an email like that at work I'd be completely freaked out and would probably go straight to HR.
Pressed send too soon... No clue on how to develop some kind of relationship with him other than the usual advice that's all over the forum, but an anonymous email at work is not the way to go about it.
It depends what your workplace is like...could you offer to make the hot drinks for everyone and so offer him one too? I agree with @Broccoli that an anonymous email is a bad idea. It’s going to come across as creepy, even if that’s not your intention.
Thank you for the heads-up. It did occur to me that an anonymous email would come off as weird at the very least. I simply don't know what else I could do. It seems it would equally be inappropriate to reveal my status or to ask him out out of the blue at workplace (not that the current practice of social distancing is permitting it anyway). We simply don't have the chance to mingle much beyond the rare exchange of a few seconds' worth of pleasantries, and I can see a face-to-face encounter would freak him out, him being in the closet as well. It is a catch 22. Both of us would be cautious of being outed prematurely, and neither would want to make the first move.
Do you think that sending him an email seeking advice on a vaguely work-related but rather trivial issue would work? If he is interested, we have a line of communication opened up (everyone is working from home now). If he is not, he probably won't reply or would reply in a cold avoidant way (as he sometimes seems to be when we meet). It is driving me nuts, virus and all. I just hope I could get a closure on this matter as I have the crush for more than a year!
Just to add, we have never exchanged emails, but since he has his online, would it still be creepy and unprofessional?
If you have other emails from work, you could send a group email and include him. Since you two never talked, sending him anything one-on-one could back fire unfortunately. Most likely you may have to wait until work goes back to normal if you expect anything to come out of it. Once it does, you will have to initiate some conversation and go from there. Don’t be pushy, just start small and slowly add on to it.