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The first five dates are a literal minefield of inopportune sweating, nervous rambling, hesitant touching—god help us all—and regular-old excitement. Add to that some last-minute panic of what you should wear, and you might just give up and order Seamless. But delivery can’t cuddle, and you can’t live with roommates forever. So we are going to help you lighten the load by planning your first five dates for you. Plus, we’ve enlisted the expert advice and handsome mug of our own Mark Anthony Green, a.k.a. the GQ Style Guy, to show-and-tell you how to ace your first five looks. This no-fail blueprint will have you looking sharp and earning points. Pay attention.
Date One: Chill Dinner
Find someplace quiet with cozy seating, then go do something cool. The vibe should be casual but not aloof. Don't let the night end before you find out her last name.
Style Guy: "I wing every moment of my life except a first date. Make a solid dinner reservation, plan a post-dinner activity, and—most important—wear a pair of boots. Boots give you one or two extra inches and make you stand up straight. Chances are she’s in heels, so they'll help even the score. I’ve had some great first dates. And some, um, not great first dates. (Like the time my date hit me with a sales pitch to join a pyramid scheme mid-dinner.) On most of my good first dates, I wore the newest pickup in my closet—the piece I was most excited about. Deion Sanders wasn’t lying when he said if you look good, you feel good; if you feel good, you play good; if you play, good they pay good. And these Saint Laurent distressed jeans definitely have me feeling good."
Henley-Dolce & Gabbana $375, available at dolcegabbana.com
Cardigan-American Eagle
Pant-Saint Laurent from Mr Porter $750, available at mrporter.com
Watch- Tag Heuer $2,150 available at shop-us.tagheuer.com
Date Two: Saturday Stroll
Plan for a day of curated wandering. Your best bets will be book stores, galleries, and insanely good ice cream.
Style Guy: "Day dates are the trickiest because you don’t know how long you guys will be hanging. Maybe two hours for lunch. Maybe 13 hours for a marathon of art galleries, bar crawls, and other shenanigans. Play it safe and wear shoes that can pass in a fancy establishment but are also super comfortable (like these Public School sneaker/brogues). Oh, and don’t wear a hat. They're not versatile. A fedora looks too dressy for ice cream and bookstore hangs. A baseball cap looks too undercover-celebrity for a nice restaurant. So leave the hat at home for a day date unless you’re actually hiding from someone—in which case, you might want to worry less about your clothes and more about what you've done."
Shirt- A.P.C. $280, available at usonline.apc.fr
Pant-Theory $235, available at theory.com
Date Three: After Work Drinks
Choose your bar wisely. If you're meeting on a weekend night be wary of places that are too loud. Unless of course, you're planning on taking advantage of the old "let's go some place quieter" line.
Style Guy: "One of my favorite Jim Moore Moments of Wisdom is his definition of how to actually dress sexy in this modern era. If you’re wearing a power shirt unbuttoned to your navel or a super tight T-shirt that says you’re the proud owner of a Bow-flex, you’re doing it wrong. I am a bit of a traditionalist when it comes to color, however. Going out after-hours? The darker your palette, the better. All black is never, ever a bad call."
Sweater - Handvaerk $95, available at handvaerk.com
Pant - Saint Laurent from Mr Porter $750, available at mrporter.com
Coat - Michael Bastian
Date Four: Brunch
Do the baller thing and make reservations for brunch. Oh yeah and be ready to meet "the friends".
Style Guy: "Don’t. Overdress. For. Brunch. Seriously—she knows by now that you’re into clothes. She knows that you read GQ Style and can call out Hedi Slimane’s final Dior collection piece by piece. Don’t show up looking dolled up when she's fighting a hangover, just trying to get some bacon in her system. Not that you should look slouchy, either. On this day, John Elliott is your best friend. Find some sweatpants that fit and be easy with everything else. If you’re fighting your own hangover, a cap and sunglasses are kosher. One more thing: cologne is more important here than any other day. Having a unique scent will lift a basic T-shirt and simple white sneakers. If you don’t have a signature cologne, go get one."
Shirt- Buck Mason $24, available at buckmason.com
Pant- John Elliott + Co $185, available at johnelliott.com
Jacket- Gant $950, available at gant.comShoes- Adidas Stan Smith $90, available at adidas.com
Date Five: Romantic Dinner
Here's your chance to impress. Take some initiative and ask for the best table in the restaurant. Flowers may seem old-fashioned but they're also a sorely neglected tradition and an easy way to get a smile.
Style Guy: "Tonight, you’re Jay and she’s Bey. You’re Brad and she’s Angelina. (Or you’re Brad and he’s Brad because heteronormative worlds are lame.) Anyway, tonight, you two are royalty. Tell her days before that the two of you are going to do some fancy shit, like eat some fancy food amongst some fancy people, and that she should wear some fancy clothes. Then pull out your sharpest suit. You might not be a magenta two-piece kind of guy, but find a suit that makes a statement. Even if you guys aren’t going to an exclusive movie premiere or the most-hyped restaurant in the city, when you walk around, people will assume you own the joint. And that’s half the fun."
Suit -Calvin Klein Collection $1,295, available at calvinklein.com
Shirt - Bespoken New York $225, available at bespokennewyork.com
