Go for broke. You’ve gabbed with the guy a few times, and you feel like he could be a buddy. Now the really awkward part: proposing a meet-up outside of wherever you two normally run into each other. Again, group settings like bars will feel less threatening than a one-on-one situation, Bonior says. Try planning a barbeque or bar night with some other people you know, and invite your new acquaintance to join in.