Hi, Dan, 26-year-old woman from Australia here. I am flying to Italy on Saturday for a three week visit with my 29-year-old boyfriend while he is studying there for three months. Problem is, I want to break up with him. What's the right way to do it? Before I leave? While I am there? When I get back home to the other side of the world? We have been together for a year and a half.

Can't Impersonate Amorousness Obviously

An easy one to start the week: Ask yourself what you would want if the dumpshoe was on the other dumpfoot, CIAO.

Would you want the boyfriend who was about to dump you to join you in Italy for a three week holiday? Probably not. It would make for an awkward few weeks together, particularly if he couldn't convincingly impersonate amorousness. You would sense the breakup coming, you would feel excruciatingly awkward at the start of his visit, and utterly miserable by the end of his visit—even if he didn't dump you during his visit, which he probably would. (The stress of traveling together has a way of forcing "It's not you, it's me" out of our mouths.)

But let's say he could convincingly impersonate/fake amorousness. Would you want him to come to Italy then dump you after he got home? Or on the last day of the trip? Probably not, CIAO, because you instantly realize he'd intended to dump you all along and that the three seemingly romantic weeks you'd just spent together were a fucking lie. (And not a feeling-sparing, face-saving one like, "It's not you, it's me.") You would wind up feeling humiliated by the fact that you didn't see the breakup coming—there you were getting pity fucked by a soon-to-be-ex instead of lusty fucked be some hot Italian boy(s)!—and you'd feel hurt and angry and duped.

That leaves one option: Being dumped before he came to Italy. That'll suck, of course, no one likes being dumped. But the pain of the dumping won't be compounded by the pain of spending three awkward weeks together before being dumped or the humiliation realizing that you'd been duped/pity fucked for three solid weeks.

Tell him it's over, cash in the ticket if you can, eat the cost if you can't—or dump him, get on that plane to Italy, then get on a train and go to Germany or Croatia or Spain instead and alone.

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