Break-ups are never easy, and it's even harder when there are issues of money involved. When you dish out the money to plan a vacation with a partner you always run the risk that you'll break up before the trip, but that risk literally applies to any planning as a couple.
It obviously sucks to lose a large wad of cash on a trip that is canceled or dampened by the painful existence of a break up, but it's generally far more emotionally messy to force a trip with an ex right after cutting ties.
"AITA for still wanting to go to Hawaii after breaking up with my girlfriend?"
Of course, now that he's broken off the relationship of two and a half years, it makes the logistics of the trip deeply awkward.
"My girlfriend and I had been together for 2 and a half years. Before my decision to break up we had bought a vacation package together for her sisters wedding in Maui. She was short on splitting the cost so I covered $1,700 of the $2,500 total cost."