Paradise Lust

I want to break up with my girlfriend, but we are supposed to go to Costa Rica and have already paid for the house we're renting for the month with her friends. Is it ridiculous to wait till after Costa Rica to break up?

--I Sound Like A Jerk

When you put off canceling a relationship to avoid canceling your vacation, even posing for photos can get complicated. You might find yourself trying to put a native person or pre-Columbian artifact between the two of you to avoid blurting out, "Hey, can you stand a little farther away from me? It'll make it way easier to crop you out." Unfortunately, you can't do much to cushion the blow when she invariably squeezes out of you that you stuck around long after you stopped loving her, which will make her feel stupid and humiliated, in addition to the usual fun feelings that come with being dumped. Barring some immediate need for your emotional support (like your partner's grandma's impending funeral or bail hearing), the kindest thing you can do is break up as soon as you know it's over -- even if it bummers up your travel plans and means you'll eat some costs. Letting your girlfriend go without you to Costa Rica might allow her to look back fondly on both the relationship and the vacation -- in a way she couldn't if she were flipping through her trip photos saying, "And this is the guy who wanted nothing to do with me kissing me under a jungle waterfall."