A few weeks ago I recognized a guy sitting by himself at the bar who is kind of a local celebrity. I was a few drinks in, so I went over and said “hey aren’t you____?” He invited me to sit down and we talked for hours, he bought me a drink, and it was a lot of fun. I don’t really ever deliberately flirt with anyone, and I didn’t think I was flirting with him very much, so I was surprised when he walked me home at the end of the night and he went in for a kiss. Cool! I ran into him a week later and the same thing happened again (super chill, great conversation) except later that night he took me to a place where he’s a regular, and I met some of his acquaintances/friends. So after another good night I texted him that I wanted to see him again. He agreed enthusiastically, and we found a day that we’re both free. He’s also 10-15 years older than me.
Now things get hairy. I heard a few days ago that he’s not single. Hmm… A little internet hunting (I know this is really stupid/weird and I shouldn’t do it, for my own sanity) and I find he’s claiming to be single, but there are definitely a lot of fishy things that lead me to believe he could have a (younger) wife or girlfriend-but he doesn’t acknowledge it publicly because of his popularity. I think it would be fun to see him again, but I don’t want to look like one of Tiger Wood’s special friends. How do I figure this out without seeming mad paranoid/insecure?
There’s nothing to figure out. You’re not gonna marry this guy. You’re not even gonna make girlfriend status. You’re gonna see him a few times, earn your starfucking merit badge, and then move on.
That’s cool. Nothing wrong with having some fun. Just don’t kid yourself into thinking that you’re signing up for any kind of relationship.
He’s got age, a little celebrity, and a reputation that obviously precedes him. Single or not, this guy is a walking red flag collection. You are not the only girl he’ll be bending over hotel room furniture, and if you can’t handle that, it’s probably best you don’t go all googly eyed.