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Your First Weekend Away Together


There's no better way to get to know someone quickly than to travel with them. Here, 5 tips to make sure your first weekend away won't be your last!

By Molly Lyons

Long walks on the beach. Afternoons in front of the fire. Dancing under the stars. Suffering in intestinal agony so he doesn’t find out that you actually go to the bathroom. Yes, we’re talking about your first weekend away with your new flame—the reality rarely matches the fantasy. Which is not to say that you should contain your relationship within the city limits. In fact, says Katharine D. Dyson, author of 100 Best Romantic Resorts of the World, “There’s no better way to get to know someone quickly than to travel with them.” Why? Because our “travel personalities” are really just an extreme version of how we act every day—good and bad. So, before you pack your bags, consider these tips to manage your vacation expectations—and make your first getaway just great.

1. Where will you go?
The surest way to turn a dreamy vacation into a nightmare is to have undisclosed expectations, says Laurie Moore, Ph.D., a licensed marriage
This is an important talk to have prior to hitting the road…
family therapist in Santa Cruz, CA. The key is talking about your destination in great detail before booking any tickets. For example, exactly what does he mean when he says he’d like to “rough it?” Is that Holiday Inn roughing it or Survivor roughing it? Put your cards on the table and then choose a location where you’ll both be comfortable—it may not be your fantasy destination or his, but no one will feel out of their element. If one person’s an avid camper but the other is bug-phobic, how about renting a cabin in a state park versus unrolling the sleeping bags? And remember, the point is being together, not where you’re going.

The other conversation to have ahead of time: Money. That is, how much are you planning to spend and who will pay for what. Think not only about big-ticket items, like the hotel, but all the incidentals, such as gas, tipping, kayak excursions, etc. This is an important talk to have prior to hitting the road… if you are the kind to grab some fried clams by the side of the road for dinner, but your sweetie is expecting a formal, four-star meal—better to know that now, and work out a mutually-acceptable plan. “Having one frank conversation will save you from awkwardness and resentment while you’re away,” says Moore.

2. What about the B&B fantasy?
For many of us (especially women), the perfect weekend away is one spent at a cozy B&B in a quaint town, having afternoon tea and sleeping surrounded by chintz. A word to the wise: Guys are usually not to keen on afternoon tea, chintz and the abundance of throw pillows that usually come with this territory. So don’t assume he’s as into the fantasy as you are.

Also know that a good number of B&B’s give new lovers very little privacy: Some just consist of a couple of extra bedrooms and one shared bathroom in a family’s picturesquely-located home. Some have very thin walls. Some only serve breakfast from 7 a.m. to 9 a.m., not the most romantic of time slots. So go ahead, make that call before booking, and find out the details.

3. What will you pack?
Perhaps there’s no better barometer of your travel personality than how you pack your suitcase (or your knapsack… or your trunk).
Somehow between here and there, I got the flu.
“My boyfriend can never get over my ‘throw it in and go’ method,” says Katherine Fullerton, a doctor in Washington, DC, who swears she can get ready for a week-long trip in less than 30 minutes. Her boyfriend, on the other hand, plans out what he’ll need for each day, makes sure it’s neatly ironed, folded and rolled. “I learned a lot about what kind of travel partner he’d be that first time I saw his, um, highly-organized packing style,” Fullerton recalls. “He had an outfit for every possible occasion, a bag of guidebooks, even a cooler packed with snacks for our drive up to the mountains. It seemed kind of insane at the time, but I must admit, I’ve come to like it. We complement each other.”

“Differences don’t always signal problems,” says Moore. In fact, “They may be great opportunities to figure out what you each can contribute to the relationship.”

4. What will you do when you get there?
OK. You’re at your quaint inn/all-inclusive beach resort/mountainside camping site. Now what? What if you plan to spend the day lazing on the beach reading Confessions of a Shopaholic and he’s booked a half-day adventure hike to the local ruins. Will your vacation also be ruined? Not if you remember two things: First, your activities, like your destination, will involve some kind of compromise. Maybe you do an afternoon sail, which he loves, and the next morning he sucks it up and joins you for a few hours of outlet shopping.

And second, you don’t have to spend every second together. If you go your separate ways for an hour or two, no big deal. In fact, there’s less chance you’ll get sick of each other. “The first time my boyfriend and I went away, I thought we had to be glued at the hip,” says 37-year-old Dawn Abrams of New York. “I thought if we didn’t want to spend all our time together it meant we weren’t compatible. But that got old pretty fast. By our third trip, I was happy to see him go off mountain biking for an hour while I had a hot-stone massage.”

5. What happens if the best-laid plans go wrong—oh, so very wrong?
Keys get locked in cars. Rain falls when you don’t have an umbrella. Hotels lose reservations. Planes get missed. What’s important is to stay focused on the fact that you’re together and you can get through it in good spirits. “My boyfriend and I live very far away,” says Norma Jean Pratico, of New York, who met her beau when he was in town for business. “We planned to meet for our first weekend together in-between our two towns. Somehow between here and there, I got the flu. I was sweaty, feverish, shivery… you name it. But he was wonderful. He got me soup and tissues and sat with me in the hotel room. I felt lousy, but in truth, it was a wonderful weekend. It totally bonded us.” It’s those moments of discovery that make the best souvenirs.


Molly Lyons is a freelance writer who frequently contributes to Happen magazine.
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