My boyfriend of eight months is going on a trip of a lifetime over the spring break. It was booked and planned before we got together, and consists of a group of friends. He has just told me one is his ex-girlfriend whom he broke up with right before we started dating. They have been friends their entire lives as their parents are best friends. They dated a year-and-a-half in total after he ended a marriage of 25 years. Things are going really well, and I want to give him the benefit of the doubt here. He was at least open enough to tell me. Some of my friends think this is a deal breaker, but I really don't want to judge him before the trip even happens. It's one of those things where deposits would be lost, and it's on his bucket list.

What Would Dan Do

You've got it backwards, WWDD — and so do those alleged well-intentioned friends of yours screaming "deal breaker!" in your ear. You're afraid you're going to lose him if he goes on this trip with his ex. And you might. But you're definitely going to lose him if you force him to choose between you and this bucket-list trip and/or his lifelong friend. Even if he doesn't go, even if he forfeits his deposits and unfollows all his friends on social media (so he doesn't have to watch everyone else enjoying the bucket-list trip he's missing out on), his resentment for you will grow and eventually he'll dump you — if not for his ex (and most likely not for his ex), then for someone else.

Look, WWDD, if you and your boyfriend are going stay together — for five more months or fifty more years — you're gonna keep running into this lifelong friend/ex of his. How you deal with her presence on this trip will set the tone for their relationship going forward, your relationship with him, and hers with you. Putting him in a position where he has to choose between someone he's known and loved all his life (and briefly dated) and someone he's known for eight short months — even eight great months — well, what would you do, WWDD? Lord knows your so-called well-intentioned friends would be screaming "deal breaker!" and telling you to dump your boyfriend for being so insecure and controlling.

As for your nervousness around the potential cheating: this trip isn't your boyfriend's only opportunity to sleep with his ex. He could fuck her on a Tuesday afternoon during a long lunch break if he wanted to. But he (probably) doesn't and he (probably) won't because he dumped her for a reason (which I'm guessing he's shared with you) and is now dating you for all sorts of good reasons. They were friends for far longer than they were lovers, so it's best for you to view their relationship as the former and not the latter. And unless she's done something to undermine your relationship with her lifelong friend/very-recent ex, you should regard her as a friend too — they may not have wanted to be together romantically, but without a doubt their opinions matter to each other and her support could be crucial if you two ever hit a rough patch. Because she's likely to be the friend he turns to for advice. If you don't want her screaming "deal breaker!" into his ear at the first opportunity, you'll let him go on this trip with minimal fuss — ask for some reassurance, and then drop the subject once its been offered.

Oh, and what would I do? I'd let him go — indeed, I did let him go. I met my husband three months before he was to go on a long-planned backpacking trip through Europe with a guy he'd briefly dated before we met. I didn't tell him not to go, WWDD. Indeed, I encouraged him to go. And I think that's part of the reason why he's still here.

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