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Have A Wonderful Weekend Away

Planning that first getaway for two? Follow this simple advice from our duo of etiquette experts to make it a smashing success.

By Phineas Mollod and Jason Tesauro

ong before pondering amour’s weightiest questions (“Will you marry me?” and “Do you want to, like, move in together?”), a playful query comes across your bow: “Wanna go away next weekend?” To a budding romance, the weekend getaway is like lighter fluid to the weekend BBQer— an ideal accelerant for turning up the heat. A successful weekend getaway offers relationship-builders that are nearly impossible in the piecemeal world of busy dating. Besides any sexual desserts, expect a main dish of tasty confessions and get-to-know-you-better talks lasting until sun-up. Ready to graduate from Dating’s ABCs to B&B? Here are our top tips for maximizing a weekend pass.

When is the time ripe?
Unless it’s ridiculously early in the relationship, the weekend getaway is rarely a bad idea—it’s not like you’re asking for her PIN # or for his help with a move-in to a 5th floor walk-up apartment. A prior meet-and-greet with workplace pals and at least a
To a budding romance, the weekend getaway is an ideal way to turn up the heat.
couple of sleepover dates provide a baseline of comfort that you’re not the Downtown Strangler or some other antisocial deviant who sleeps inside a pentagram.

In the end, there’s no requisite number of dates to wait, but when affections are steady and the desire to spend bigger chunks of time is clearly mutual, go ahead and book reservations. And when weather or fate mandates spontaneity, don’t fuss over the right wording: “The forecast calls for another week of hot and humid—whaddya say we hit the beach?” Or, “You, me, the Cherry Blossom Festival... got a suitcase handy?” If timing is off, both sexes are perfectly capable of declining a premature invitation with a polite “Darn, I’ve got plans that weekend” that sidesteps awkwardness without derailing the whole relationship.

Destination decisions
Sum-sum-summertime is the high season for getaways, yet the calendar is ripe anytime from verdant May through the fall foliage season, with intermittent winter blips for island jaunts or ski-cabin canoodling. When planning, keep in mind that beachside and cityscape outings are less confrontational than wilderness/camping trips that boast total isolation and no chance of escape if things go south. Joined by ropes and carabiners for 48 hours, even two North Face-wearing trekkers might prefer an avalanche over another night in a 5’x 5’ tent. Furthermore, off-season trips to hot spots might be ideal for a low-fare holiday of hotel sex, but an empty seaside hamlet leaves little for two introverts on their first weekender starving for stimuli. Similarly, a quiet country house may be the most romantic, but never rule out a group outing at a share house, which remains a casual option for couples early on in their courtship…provided, of course, that the other housemates aren’t your parents.

Sticky situations, solved
Privacy: No matter if beach-house passions have ignited in the outdoor shower, a couple’s first weekend getaway is still uncharted waters on the privacy front. Clothing may be optional after midnight, but each sexy mate must respect bathroom space. Moreover, even if you’re looking for suntan lotion, don’t go rooting around toiletry kits
A getaway usually implies that sex is in the air. Triple your wooing efforts and you might need to double the length of your stay.
or overnight bags. True, you may unearth lingerie or toys, but on the dark side, your prying may uncover prescriptions and embarrassing ointments that weren’t supposed to come to light until the one-year anniversary.

Money: Akin to the first date, the weekend host generally pays for lodging, car rentals, and fancy nights on the town. That said, conscientious guests should handle their own train tickets and chip in for gas, chartered fishing boats, and wine-store receipts. If all goes swimmingly at the lake retreat, it isn’t improper for a guest to at least offer their share of plastic at the front desk when the bill comes. However, if $500 a night accommodations didn’t jumpstart an iffy romance, the host must chalk up the tab to experience, even as the guest numbs the pain of this flop with spa services and raids on the overpriced mini-bar.

Sexpectations: While it’s not a blanket agreement for agreement under the blankets, acceptance of a getaway invitation usually implies that sex is in the air. When you’ve already slept together and put a dent into a 12-pack of condoms, a weekend getaway is the logical next step for further exploration. If the relationship is unconsummated, an escape promises the scenic vistas, cozy room service, and high thread-count sheets befitting the “first” time. However, like a professional golfer going into Sunday with a 3-stroke lead on the back nine, the privilege is yours to lose. Act like a presumptuous ninny, and you’ll go to dinner without bed. On the other hand, triple your wooing efforts and you might need to double the length of your stay.

Incidentally, if you’re not sure that sex is on the itinerary, go ahead and book accommodations with two double beds. If relations stay PG, you’ll be branded the gentleman who took no liberties. If all goes well, you’ll have extra pillows and more covers to muss.

Misery: What if it sucks? On rare occasions, a long romantic weekend devolves into a cold-sheeted Friday night and a dismal Saturday morning of incompatibility. If cupid’s coroner has pronounced this love affair DOA, there’s no shame in pulling the plug. Sometimes, sparks are smothered by poor logistics (e.g., enduring a 10-hour hellish drive just to get to a ho-hum cabin); other times, the charm and glamour in the brochure never materialized. Don’t feel compelled to suffer through the situation. A frank comment—“We don’t seem to be having the great time we thought we would…”—can bring a disaster to a gratefully early end. And look on the bright side: When the oceanfront or leafy environs are especially lovely, perhaps a new solo adventure awaits you in a motel room for one.


Phineas Mollod traded his J.D. for the editorial life and is often found riding the congested E train with his wife and daughter in New York. Jason Tesauro pushes pen and ink by day and leads the MGAffairs.com lifestyle seminar series by night, ne'er far from his sweetheart and a Brady Bunch houseful 'o tots in Virginia. Together they are the authors of The Modern Gentleman: A Guide to Essential Manners, Savvy and Vice and The Modern Lover: A Playbook for Suitors, Spouses, and Ringless Carousers.
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