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How do I ask a coworker to hang out?

I’ve been working at this place for about three months now. With that particular coworker, we haven’t had too many shifts together, but we do chat whenever we can. We’ve even gone home together a few times, and while I’m not 100% sure (sometimes I have a hard time coming up with topics to talk about) we banter a bit. Recently, he messaged me first with a picture of a thing we talked about previously too.

I’d like to get to know him better and was thinking it might be fun to hang out outside of work. But I’m not sure how to ask him. I’ve tried dropping hints about grabbing drinks or going out after work, but it hasn’t worked. I think the library might be a good option since I know he goes there sometimes, but I’m not sure if he goes alone or with friends.

Any tips on how to approach it? Should I start messaging him from time to time to build familiarity? If so, what about? I struggle with messaging people I don’t know well as I don’t want to come off as annoying. ;w; I also don’t know if he has anyone, so while I would be interested I don’t want to cross any boundaries.
#relationships
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