Dates Women Love

Want to pick a place that’ll wow her? First, suss out who she is…then follow these tips. Whether she’s busy, brainy, or shy, here’s where to go.

By Phineas Mollod and Jason Tesauro

ver make eyes at your date… and find her trying desperately to mask the fact that she’s uncomfortable, impatient, or bored? Never fear, guys. While it’s easy to assume you’re the problem, her issue might have more to do with the place you took her to. Fact is, certain women flourish — and founder — in specific surroundings. Learn to match her personality with outings that accentuate her strengths, and you’ll be amazed how much easier it is to get the rapport rolling. Only how? Don’t fret—like a personal sommelier, we’re right behind you with pairings that’ll leave your date wanting seconds.

If she’s the super-busy type…
For a woman who works long hours, is raising kids on their own, or is otherwise time-pressed, every hour of her day counts. So, the last thing you’ll want to do is take her to a
The essence of romance lies in showing that you’ve been listening.
restaurant where there may be an hour-long wait for a seat or lure her to some out-of-the way venue (the longer the drive, the less happy she’ll be when she arrives). Instead, prove you understand her plight by demonstrating your adaptability to her lifestyle and routine. How about a morning scone together before work at a café around the corner from her office or an evening coffee break at a park near her home? Or, even better, plan an in-the-office picnic for lunch or dinner (if she’s working late), complete with champagne and stolen kisses at 9 p.m. as she waits for a fax from the Indonesia bureau. Another strategy is to piggyback on plans she already has on her agenda. Whether she’s booked with a Tuesday night book club, Wednesday yoga class, or a boring Sunday night at the supermarket, tag along and suggest a small rider to her agenda, like “After your errands, let’s chat over a restorative wheatgrass juice.” Show her that she can have a relationship and her life as she likes it, and she’s yours.

If she’s the shy type…
As much as she wants to be the apple of your eye, a woman who’s on the quiet side can be uncomfortable in the spotlight. To keep her from feeling self-conscious, avoid pin-drop quiet, conversation-heavy dates that put too much pressure on her to be an extravert (coffeehouse, white-cloth dinner). Instead, try an “activity date” where rapport builds through sharing an experience, not just straight conversation. A long bike ride or hike, roller- or ice-skating, cooking or pottery class allows chemistry to simmer slowly, permitting for long lapses in conversation as you’re consumed with completing a task. Or, since she may feel more comfortable with her support network nearby to back her up and draw her out of her shell, suggest a double date with some of her friends. By working with her comfort zone, she’ll open up in no time and perhaps even connect her newfound confidence to you.

If she’s the brainy type…
This gal thrives on good conversation, so make sure you can have one: Choose a venue that’s quiet enough that you can easily hear each other (no rowdy bars or clubs), and if there’s edgy artwork, an open-mike poetry slam, or something else thought-provoking to kick off a sparkling dialogue, all the better. Or, try an activity that works her brain, whets her competitive instincts, and yet reminds her that life is not one big Debate Club: Break out some board games. Woo her over cards, Connect Four, or Battleship, or broaden her horizons and learn a new game together. But keep in mind: Smart sorts appreciate guys who can show them how to break out of their intellectual straightjackets. So try getting her to goof off and giggle by taking her somewhere that fulfills her unspoken hunger for kitsch and canned beer. Chances are, your saying, “That’s right, we’re going bowling—I can’t wait to see you in those funny shoes” will get you two bonding faster than a book lecture any day.

If she’s the wild type…
Charming this fun junkie requires preparation. Since she craves more stimulation than most, the hits must keep on coming should a date run into extra innings. A daylight
Make a date that breaks some rules.
date might start with a rollicking bout of paintball or mini-golf; an early evening might begin with a gallery walk, followed by drinks at a newly-opened hotspot, and then hit an underground club or a house party boasting a hot tub. Sometimes, noisy fun isn’t necessary, just something novel: “Have you ever been to the roof of the Thompson Building during a full moon? I know a way up” or “Have an espresso… we’re going night skiing.” Show her some hidden gem in the city that she swears she knows inside and out, and your stock will rise in her eyes. Another surefire tactic: Make a date that breaks some rules. Convince her to play hooky from work one day to gallery-hop and art will never seem so exciting. Eating dessert before dinner will have a conspiratorial edge. This woman craves small rebellions; prove you’re a bit of a bad influence, and she’ll be hooked.

If she’s the romantic type…
These dreamy sorts, you might assume, long to be wined and dined at five-star establishments, right? On the contrary, the essence of romance lies less in grand, sweeping gestures than in tiny touches that show you’ve been listening. If her online profile mentions a love of Indian food, suggest such a great tandoori spot for your next rendezvous. If she’s recently finished a big work project, give a toast to her job well done. If you’re planning dinner at home, bring her favorite ice cream, or a bouquet of her favorite flowers or a videotape of her favorite movie. If you haven’t known each other long enough to have sussed out her preferences, suggest a date that carries some traditionally romantic trappings and a touch of nostalgia: a carnival (with cotton candy and mandatory make-out on the Ferris wheel), the zoo (watching critters scurry around is bound to breed some warm-and-fuzzy feelings), or a black and white movie (they just seem so much romantic than today’s blockbusters; if you’re renting and are not sure what to get, you can’t go wrong with Casablanca). Take a weekend day trip to a quaint town or vineyard; watch for romantic hotspots by strolling down the old Main Street, past historic homes and inns, and certainly share a cocoa at any mountain chalet advertising rocking chairs and a breathtaking view. Now, that’s what we call impressive wooing.

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 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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