Should I End It After Our Vacation?

For the best advice on sex, love, dating and relationships we ask two experts with personal experience. Cathi Hanauer is the author, most recently, of Sweet Ruin, a novel about love, marriage, and adultery. Daniel Jones is the editor of both the "Modern Love" column for The New York Times, and Modern Love, an anthology derived from the column. They have been married for 15 years. Together they provide a his and hers take on relationship questions. This round: when's the best time to break up?

Question: My girlfriend of two years and I are traveling to South America this fall to attend her best childhood friend's wedding. We've been planning this trip for almost a year, including two extra weeks of trekking in the Andes with some friends afterwards. Here's the problem: Without going looking for anything, I met someone else, and I want (and need) to end my current relationship, even though it kills me to think of hurting my girlfriend. If it weren't for this upcoming trip, I would have already done it. Should I tell her what's going on before we go or after we get back? —R.S., Boston, Mass.

Dan: Tell her your feelings now—the sooner the better. If you've already sunk a lot of money into the trip and still hope to go trekking with her after the wedding "as friends" (yeah, right), you'll need some time to start pleading your case. If you're able to get her on board for the notion that it might be nice to have this trip together as a grand fade-out for your relationship, then you lucked out. (But be warned: It easily could turn into an awkward, conflict-ridden bitchfest.)

Why not postpone telling her until after the trip? What harm is a little extended ignorance? Simply put, any enjoyment she has on the trip will be undone once she realizes it was all a fraud. The gift of ignorance you gave her will be a hollow one, because she'll realize, after the fact, that every kindness you offered to her, every kiss, every hand held, every conversation, was a patronizing lie.

Of course, there is another option—a truly devious master plan—but I'm ashamed to suggest it. In fact, I'm ashamed on behalf of all men for even allowing the idea to gain currency in my mind, because if I thought of this, then I know many other men have too, and, well, that's just despicable. But here it is (forgive me): Go on the trip, have fun, have sex, act loving, come home, wait a month (or, preferably, two), then tell your girlfriend you've fallen in love with someone else. Granted, this route would require an Oscar-caliber performance (not to mention an extremely patient new girlfriend). But if you could pull it off, it might preserve the trip as a wonderful (if still technically fraudulent) experience for your soon-to-be ex.

All of which, I hate to say, raises the question: Who says Flame #2 will stand by as you go off to South America with Flame #1? Doesn't she have an opinion in this little soap opera? Don't you think she might be blessed/cursed with the same wandering eye as you? Which raises another question: How can men be such liars and so trusting simultaneously? Talk about the gift of ignorance!

Cathi: Not telling your girlfriend before you go isn't fair to her, the new person, or—say it with me—yourself. And having been in the same hiking boots at one point, I have to ask why you'd want to go on a trip with one girl when you're itching to be with another. (OK, the mountains, the spiritual thing … but still.) Then again, I can't imagine how you can be with her now while feeling this way. Maybe it's just me—bad poker face, and all that.

Anyway, how generous is it, really, to let her get that much more bonded with you and then tell her, "Sorry," but you've actually been in love with someone else for months now? (I know, you wouldn't tell her that part, but, believe me, she'd find out.) She'll be hurt either way, but if you wait, she'll also be enraged at having played the fool for so long. As for the trip, unless you're a master of deception, she'll sense something's changed between you and won't know what or why. Nothing like that for a scenery wrecker.

You need to drop the bomb—or, rather, place it down gently—like, today. Then it's her call. If she opts not to go ahead with the trip—or to go on her own or (sorry, dude) with someone else—you'll have to suck it up, since (a) she's the one invited to the wedding, and (b) you're the one doing the dumping. Best-case scenario, she'll agree to go with you as friends. And if her next boyfriend happens to be seated on her other side at the wedding, she can tear up the dance floor with him while you daydream about your new girlfriend back home.