How do I approach asking a shy guy if he's interested without coming across as aggressive?

I work with this guy who is a notorious loner. But he and I used to chill all the time and I feel like we really get each other. We even flirted subtly back and forth and shared private jokes. I'm really into him but we're both kinda shy and awkward. I hung out with him out at a bar for the first time a little while ago and he got very sweet hugging me, and asking where I go out because he never sees me. Told me that I'm his favorite person. Etc. Every time I see him out (drunk) he's affectionate, but not handsy in the obvious way. He holds my hand and puts his arm around me. Gives me long hugs. But when we're around each other sober it's awkward now. Not like avoiding each other, but not comfortable like it was. Is there a way to ask him what's up without seeming desperate or confrontational? And should I?


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Most Helpful Girl

  • Simply ask him what you want to clarify. You can be polite, but you can't control how he interprets your approach. Just talk to him.

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    • That's a good point. Thanks!

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