How should I (28/F) approach him (34/M)

There is a man I'm interested in who I don't know very well, but I've seen him around a lot. Due to being shy I've never had a true conversation with him. We're Facebook friends though because we run in the same general social circles. We matched on OKC a few years ago and chatted one night but it never went anywhere, possibly because he ended up dating someone else. I thought he wasn't interested after that until we also matched a few weeks ago on Tinder. Still, our conversation didn't take off because I wasn't taking it seriously and deleted the app days later. Even then I thought maybe he was one of those people where there was mutual physical attraction but not much beyond that.

However, in the past week two things have made me rethink it. First of all he's been sharing things on Facebook that show we have the same politics and that's a huge deal to me. Secondly, my boss mentioned him out of the blue in a conversation as someone she really liked and respected. Not only do I have a lot of respect for her opinion, the reasons she gave indicated that he and I share a lot of core values. I have no idea if we would or wouldn't click but I'm now seriously interested in asking him out and seeing if we do!

I have never asked a man out before. I am not afraid to do it, and I won't be offended if he doesn't want to, but I don't know what to say to him to indicate sincere interest and then ask the question!

Also, is messaging him on Facebook strange if we don't have a personal relationship or is it less intrusive to find and message him on an OLD platform like OKC or Hinge?



Submitted May 17, 2019 at 05:45PM

There is a man I'm interested in who I don't know very well, but I've seen him around a lot. Due to being shy I've never had a true conversation with him. We're Facebook friends though because we run in the same general social circles. We matched on OKC a few years ago and chatted one night but it never went anywhere, possibly because he ended up dating someone else. I thought he wasn't interested after that until we also matched a few weeks ago on Tinder. Still, our conversation didn't take off because I wasn't taking it seriously and deleted the app days later. Even then I thought maybe he was one of those people where there was mutual physical attraction but not much beyond that.However, in the past week two things have made me rethink it. First of all he's been sharing things on Facebook that show we have the same politics and that's a huge deal to me. Secondly, my boss mentioned him out of the blue in a conversation as someone she really liked and respected. Not only do I have a lot of respect for her opinion, the reasons she gave indicated that he and I share a lot of core values. I have no idea if we would or wouldn't click but I'm now seriously interested in asking him out and seeing if we do!I have never asked a man out before. I am not afraid to do it, and I won't be offended if he doesn't want to, but I don't know what to say to him to indicate sincere interest and then ask the question!Also, is messaging him on Facebook strange if we don't have a personal relationship or is it less intrusive to find and message him on an OLD platform like OKC or Hinge?
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