Update for the entitled male “friend” who wanted me to ride with him: just as I expected, he has now gotten others involved to convince me. I’m at a loss.

I'll start off with the fact that I don't think you are wrong or crazy at all. If "Ivan" just wanted some company to not be alone on a long ride I'd get that (though not accepting your "no" would still be overstepping). However, you are saying that "Ivan" gives you weird vibes in general and the way you describe this "friend" and your interaction with him, gives the impression that this is not about not driving up alone and more a possesive "but you should be with me" kinda thing, which makes it super weird.

But the friend you want to drive up with might not be aware of that. Maybe "Ivan" framed the idea a bit differently to him and he sees "Ivan" just as another friend of yours. That might help to understand why your other friend doesn't find "Ivan"'s request and pushiness weird: If you and "Ivan" were actually just normal friends, one can kind of see his argument of not wanting to drive 2h alone and being kinda annoyed of always (if you always ride with the other guy) being left out in the rain in a group of three people, just because the other two are a bit closer. Driving long distances alone is just boring and sucks. If "Ivan" approached your other friend with this argument and maybe even framed your "no" as being partly rooted in concern about leaving the other friend (who you had alreaey agreed to ride with) hanging, I can see how taking "Ivan""s side in this might seem natural and reasonable.

Just explain to the friend that you want to ride with, that you'd be more comfortable riding with him as "Ivan" gives you weird vibes, especially by being so pushy about this. I am sure your friend will understand and agree (if he is a good friend). Hope this helped.

/r/TwoXChromosomes Thread