Is It Time for a Long Weekend Away with the New Beau?

Labor Day weekend is approaching fast! And a close personal friend of mine is wondering if she should go up to Vermont with a dude she's been dating a couple of months.

She asked me what I thought — and I had my opinions, of course. But I decided to ask life coach Laurie Gerber — president of the Private Coaching Division of The Handel Group, a life coaching company — if she has any rules of thumb that might be useful for my friend (and for you) when it comes to the conundrum of whether or not to vacation with a new beau.

What's the minimum amount of time you should be dating someone before you go away with him for a long weekend?

It depends — though four to six weeks is probably a good rough estimate. If you're into him — if you think you have similar values, you can communicate openly, and you really respect one another — a mini-vacation is a great way to get a fast sense of whether you two have serious-relationship potential. A long weekend is a crash course in finding out how you really feel about each other.

Why do you say it's a "crash course?"

Being with each other 24/7 will give you a better sense of each other's habits — the good ones and the bad ones. You'll have to ask for "down" time and share it with each other. You'll get to see how he responds to a wide variety of situations.

Should you go on the trip if you two haven't yet agreed to be monogamous yet?

Discuss the sex issue before you agree to the trip.

I personally wouldn't go away with anyone unless I knew he was dating me exclusively — and unless we'd already had very good sex. Because who wants to be trapped in a bed-and-breakfast with someone for another night or two after mediocre sex? Right?

If you feel connected to someone, and the two of you are crazy about each other before you have sex for the first time, the chance that your first encounter will work out well is close to 100 percent. As long as you feel comfortable communicating, it will be intimate and enjoyable, even if it isn't perfect.

Even if he has a micro-phallus? Wait — don't answer that. But don't you agree that you shouldn't go on a long weekend with someone unless you've had sex with him first?

No. As long as you talk about it and have clear plans about what will happen, sex-wise, during your time away, it's fine to take the trip. I tell my clients that they shouldn't have sex with anyone until he agrees to be monogamous. So if he hasn't agreed to monogamy and you still want to go away with him, tell him you are going to draw the line at second or third base. Maybe even suggest separate rooms. But my company specializes in coaching single women trying to find "the one" — so this advice might not apply if you are just looking for fun.

Should you avoid any kind of trip that's too intense or potentially disaster-ridden — like camping or extreme sports — for your first time out?

Nope. As long as it's something you want to do, any vacation should be fine. If you have totally different tastes — like he wants to go bungee jumping and you want to sit on the beach — he may not be the one for you, unless you're both happy having time to do your own things. Whatever happens, don't pretend to be into doing something you're not up for! That's not likely to make either one of you happy.

Should you have a discussion about who should pay for what before you agree to the trip?

If you have any questions about money, absolutely ask. You could be in trouble, wallet-wise, if you don't figure out the finances ahead of time. Discussing it beforehand is always less awkward than talking about it when it's time to throw down a credit card. And if you're with someone who can afford the trip and wants to pay for it, it's fine to let him.

Totally. Though I think it's nice to offer to buy some little things — like lunch or drinks — or to pay for gas. Tell him you'll handle the tip. Won't he appreciate those gestures?

I agree.