sounds fishy to me. Sounds like he knows osmething or has the idea that your partier / drinker outside of work for whatever reason.
Also sounds like he is getting a bit to personal like others have mentioned and its clearly making you uncomfortable so i take this as a red flag as well.
But what really got me is hte texting you after hours on a friday night when he never has sure it might ahve been about work related stuff but at that hour etc... it just sounds like he was using work related stuff to fish around and possibly strke up a dialog about whatever else.
sounds to me like he has some sort of an agenda.
but that texting after hours at that hour on a friday night after the other things you descibed... yeah sounds fishy to me.
I dont think yoru off base feeling how you do.