Too Soon For a Vacation With the New Dude?

I feel like I've been doing a lot of talking about my friends lately — but that's because their personal lives are more interesting than mine is … at least at the moment!

The latest friend-gossip I have is by way of a buddy who's been dating a girl for two or three months, tops — who just agreed to go with her on a ski trip in mid-January.

"Maniac!" I shouted. "That's a long time from now! Anything could happen before then!"

He laughed. "She and I get along well, and I like her friends, too," he said. "If we break up before that — which I don't think will happen — I'm sure things will be amicable enough that I'll go through with the vacation. Even if I do get a separate room. Worst-case scenario, I lose some money on the ticket."

His temerity stunned me, but he's a lawyer, so he does make a ton more money than I do.

I took Sweet Pants (opens in new tab) to a wedding not long ago. When I asked him to go with me, we hadn't been dating long ourselves. But the stakes were very low: The venue wasn't more than four hours away, I was planning to drive even if I went solo, and I'd be paying for a hotel room whether he shared it or not. There were no plane tickets to buy, and no major expenses to pay for in advance.

Not so in my friend's case!

But I suppose you could argue that you have to take leaps of faith in any relationship — that if we all waited around to be sure we'd never break up with someone before planning ahead, we'd barely be going out to dinner, let alone to Colorado.

What do you guys think? Any rules of thumb, or basic advice, about when you should agree to a vacation with someone you recently started dating? I talked to Laurie Gerber, with the personal coaching team The Handel Group, about taking a weekend away (opens in new tab) with someone new, but this seems different because (A) you don't have to plan too much in advance for a weekend away, (B) people generally drive or take the train or bus rather than flying for weekend trips, and (C) weekends are a lot shorter than week-long vacations.