Don’t know if he has feelings for me

Illustration/Uday Mohite

I have a crush on a colleague who smiles at me a lot but doesn't give me any hints about whether he has any feelings for me. I don't want to say anything specific and am also wary of asking him out because I don't want to cause any unnecessary issues at the office. We have a work offsite coming up and I am trying to think of a way in which I can manage to get some time with him and just chat about more personal stuff, to find out more about him and his life. He has no social media profiles so I can't even get any information there. What should I do?
Maybe you should stop overthinking this and consider the simplicity of a direct question. If he doesn't want to go out for coffee, you won't have to think of ways to speak with him privately, nor will you have to worry about his absence on social media. Why jump through hoops when you can just make things easier for yourself by speaking to him?

My best friend and I recently met a cool guy at a party and realised we both liked him when we had a conversation the next day. This hasn't created any friction between us, but we are wondering if it makes sense for both of us to ask him out. If he rejects one of us, it may hurt the other person's feelings and we would rather stay friends than let jealousy affect us. Should we just give up on the idea completely?
Why not consider the possibility that he may not have any interest in either of you? Or, even better, that these things happen and it's okay for one adult to like another adult? Jealousy shouldn't be an issue if you are both aware of what your friendship means and why you want to hold on to it. If you like him, you should ask him out. If he isn't that important, you can forget about this.

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