Dude covers $5K worth of expenses for group vacation, friends refuse to pay him back: 'They're saying I'm being dramatic about money'

It's tough to travel with a large group and keep track of money. I've done it before, where everyone pays for a little of everything, and Venmo requests people for their share afterwards, and it can get extremely complicated. There are literally apps designed for doing exactly that because it's challenging to keep track of on your own. It's not hard to write down how much you spent on something and divide it by X, but if you paid for drinks for 5/8 of the people in your party, you might not remember exactly who those five people were seven days after your trip is over. 

If you have a small group of friends you trust, consider Venmoing as soon as the transaction happens, so you don't have to go back and try to remember who owes you what. Or, better yet, one person can cover everything, and everyone can Venmo them back a lump sum instead of multiple transactions. The latter only works if you can trust everyone in your party to pay them back. Some people are okay with paying back $10 for a drink, but they take their sweet time when their friend spends hundreds of dollars on something while you two were on vacation. Obviously, you should prioritize repaying someone who has spent a lot of money on you as quickly as possible.