he throws out lil tidbits of info which are clearly crafted to prompt an emotional response
nothing drastic or disrespectful enough for you to cut them off (he aint stupid lol), but just
questionable enough to make you feel something. ask something.
remember this:
it is an attempt at emotional manipulation which is often rooted in insecurity.
as in: even though you're there with them, and are interested...something in them needs you to validate or express your interest more.
maybe he feels another guy will grab you up if you're not as seemingly emotionally invested as he'd like you to be
i don't believe in demonizing insecurity . it can be a feeling many of us human beings cannot control sometimes.
but if they don't stop it once they clearly see you do NOT respond to that at all - making their elaborate effort pretty fruitless, it may be time to keep it moving.