23-year-old bails on $170 share of hotel room, friend considers disinviting him from beach house trip: 'Maybe you shouldn't try to plan things around me'

Ally Perry • Writer and Editor

Jun 9, 2026 9:15 AM EDT

How do you deal with a friend who owes you money?

Nobody likes being around a person who thinks that they have free rein on your wallet, but there are plenty of individuals out there who will act like that with you if you aren't careful. Whether you encounter a professional freeloader or the kind of person who is simply too good at ignoring when others go to significant expense, they are likely to cause conflict at some point.

The most important thing when dealing with this type is enforcing and sticking to some firm boundaries. Sadly, it is a lesson that many are only going to learn from experience. It is often the case of getting burned once and learning not to get burned again. It isn't nice to lose money to someone you eventually feel does not deserve it, and there is every chance this investment will not be a one-time thing. It can ruin events and things you looked forward to, purely because they are not interested in changing their behavior. Dealing with this does not come easily to a lot of people, but it is a skill worth developing sooner rather than later.

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A group of friends was planning a trip where they would share a hotel room, leading the friend who was in charge of booking to request that the other two were sure that they could go ahead with the vacation, as the room was nonrefundable. While both were initially on board, one friend ended up cancelling as he had work commitments.
The friend who made the booking was annoyed, as he felt that his needs had not been prioritized. After the cancellation and the flaky friend's reaction to his annoyance, he was considering disinviting him to another upcoming weekend vacation that he had. However, he didn't know if that was taking things too far.
Am I wrong for disinviting my friend to my beach house for the weekend because he bailed last minute on another trip that put me out 170 dollars?

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