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I'm a woman in my mid-30s and I've been dating a guy for five months now, having been friends with him for two years before that. For the past three months it's been long distance as I've been traveling. When I left home, he was very sad about me leaving and we spent a lot of time together. I just wasn't sad about it at all and started to feel claustrophobic, but put it down to the fact that it was me going away—everyone always says it's harder for the person left behind. Since I've been away he's come to meet me twice, for a couple of days each time. On Skype he's been insecure and overly sensitive and constantly picking fights and it's put me off him. I have spent hours on the phone dealing with his meltdowns. When he came to visit I dreaded it, and I was relieved when he left, although we got along ok when we were together.

This week I realized I want to end this as I can't imagine it being a long-term thing when he's so insecure. I'm heading home tomorrow, so I could do it then, but the trouble is we have a vacation booked together with several mutual friends the following weekend. My question is should I leave it until after that trip or is it better to rip that bandaid off right away? I don't want to be cruel or string him along—he's a great guy and a good friend—but I also don't want to dump him as soon as I get back after he's waited for me for three months. And I don't want to ruin/cancel this trip.

If I leave it until after the vacation it'll be three weeks from now. Is it better to date him for three more weeks knowing I am going to end it? I really don't want to be an asshole.

Mostly Undecided Madam

An easy one to close out the week...

Speaking from personal experience—bitter personal experience—you have to end this now. Because if you don't end it before the trip, MUM, you're going to end on the trip.

And that will be so much worse.

Here's what's gonna happen if you don't break up with him and try to power through that vacation: Your boyfriend is gonna sense something's wrong, he's gonna get all insecure on your ass, and then he's gonna require a stream of reassurances from you—reassurances you will hesitate to give him because you're gonna end it when the trip is over and you don't want him throwing those reassuring lies back in your face when you do end it because you don't wanna feel like an even bigger asshole then than you already do now. Your hesitancy is gonna cause him to feel even more insecure, his demands for reassurances will come at an even faster clip, you'll hedge and you'll duck, you'll try to change the subject, you'll wind up avoiding spending time alone with him, and... BOOM. There's gonna be a confrontation, MUM, an explosive one, and the relationship will be over.

But the vacation won't be.

You'll be stuck in the same hotel room for the better part of two weeks with someone who won't stop crying or wishing you were dead or both.

So either way—whether dump him before the trip or wind up dumping during on the trip—this two-week vacation you've planned for immediately after your return from three months of traveling (nice life!) is gonna be ruined, MUM. And if you wait to dump him until you're on vacation, MUM, it's not just your vacation and his that will be ruined. Your mutual friends—those innocent bystanders—are gonna be splattered with emotional gore and have their vacations ruined as well.

Break up with him when you get home, MUM. Right away. Then you'll have a week to figure out whether you can go on the trip as friends—which I think would be a mistake—or which one of you is gonna be gracious, eat the cost, and let the other go on the trip solo. Since you've been away for months, and since you're the one who's doing the dumping, he's the one who's gonna need the vacation. So let him go, MUM.