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Sex apps -- it's rude to be trying to talk with other people, or meet other people, when you're vacationing with a friend. And honestly, if he can't keep his pants zipped long enough to enjoy a vacation with you, he's got a real problem.
Hooking up with others in your room -- absolutely, appallingly, disgustingly rude, wrong, inappropriate, and inexcusable. That, alone, would be cause for me to never talk to this person again. The fact that this person thinks this is something that's OK to do should be all you need to know about what kind of person he is -- and it ain't good.
Frankly, those two items gave me the impression, that his main purpose for joining the OP on these jaunts was ....
He is not a friend when he has a hookup and forces you out of the room. If you could stay in the room and wanted to and were part of the hookup, of course that would be okay. But that was not the case. He needs to figure out how to get his own room or try to get hosted at other guy's place. Simple as that.
You shouldn't even try to be friends with him anymore until he pays you back what he owes you.
Even if you're in love with him, he doesn't respect you as a person.
Unless there's something you're not telling us such as he's an fwb on the side or something like that, you need to stop being a patsy and stand up for yourself. You can keep the conversation 1-1 and in-person but you should tell your ex-friend how you feel taken advantage of and that you want to be refunded for half the Ubers, his portion of the hotel expense, etc. Period.
I like the story and sounds funny. He's an early riser, rushes you out the bathroom, etc.
About you paying for everything are you the person with significantly more income? If you are then he will expect that.
I knew some other guys (straight) where one always paid for the other one's drinks and food as company.
He made significantly more than the other and they didn't do vacations together.
It does get old paying for the other person because all that money you paid for him could have gone to your own debts or small investing over those years. Let's say you had an extra $300-$500 or more to blow in 2012 or 2014 and put it in bitcoin or some stock. Yeah, I'd stop going on vacations with him & find another travel friend.
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