Getting Around Town With Jamie Shupak: How You Can Look Your Best on Date Night

Facts: Jamie is not Carrie Bradshaw. And don't try and date someone when you're wearing a football jersey with back hair visible above the collar.

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Complex Original

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Jamie Shupak is the Emmy-nominated traffic reporter for NY1, the Big Apple cable network that’s the end-all and be-all on all things Gotham for New Yorkers. She’s also a beautiful, single woman navigating New York’s treacherous (and hilarious!) dating scene. In her weekly column she shares her war stories and offers her advice and admonitions.

One of the most fascinating parts of writing this column (besides, of course, some of my former flames’ responses) has been the constant references to Carrie Bradshaw. Don't get me wrong, there is no more flattering a comparison. I love the woman and everything she stands for (and how she looks while doing it), but the ironic part is that we couldn’t be more different.

Sure, we’re both petite single women (with naturally curly hair!) who write about relationships and dating on a Macbook, but that’s about where the similarities end. She writes her column while lounging in perfectly put together lingerie sets while I'm in sweatpants and an ex-boyfriend’s old soccer t-shirt. She once famously said, “When I first moved to New York and I was totally broke sometimes I would buy Vogue instead of dinner…I just felt it fed me more.” Trust me when I say, this girl doesn’t miss a meal.

So, when it comes to getting dressed for a date (as my much more fashionable counterpart would say) I can’t help but wonder: Are we putting too much pressure on the fit of the jeans versus whether you and the man will actually be a fit? And, if he really is a great guy—the open doors for you, loves his grandma, always walks on the outside type of guy—and you like everything else about him except his clothes, isn’t that really one of the only things you can change about someone?

PHONE A FRIEND

Let me take you back to October. It was my first date after my breakup, and I was freaking out about what to wear. I am not shy, nor do I ever get nervous or anxious, so having these feelings was new for me. Trying to find the perfect balance of cute, hot, and sexy, all without giving too much away, was as rough as trekking through the Meatpacking District’s cobblestone in 5-inch stilettos. So I called in my reinforcements—two successful, gorgeous women who are now off the market and happy to help (and live vicariously through?) their single best friend.

The morning of the date I emailed them a full head-to-toe description of what I was planning to wear, asking for their approval. They’ve done the dating thing, so they were well-versed in proper first date dress code. They approved the baggy, off the shoulder sweater and jeans, and I’ve since sported this ensemble on almost every subsequent first date. If it ain’t broke, why fix it? (Side note, girls: realizing now that we need a new first date look for spring and summer.) Everyone should have a Mindy and Traci in their life. Guys, if you’re not sure what to wear, ask your bros, homeys, colleagues—anyone you trust who’s been there, and done that.

DRESS FOR THE OCCASION

Every morning I get up before the sun and the birds and get dressed for work. No time like 3:16 a.m. for full hair, makeup, and wardrobe. Once again, I have help from two very talented women (big ups to my best friend Jess and stylist/girl crush El Shane) who give the yay or nay on most of the outfits you see on TV. Off-air, I'm much more casual.

Each day at noon, when I’m done with work (yes, noon) I go home, take off my makeup and tight designer dress, and throw on jeans and a t-shirt. It’s all about looking the part. If I wore my afternoon uniform on NY1, I’d look like an idiot. The same goes for the guy who sports his Eli Manning jersey (or any jersey) anywhere besides a game. It just doesn’t work.You know I’m a sports fan, but that kind of attire doesn’t fly.

I dated this one guy for a while who took me out almost every Friday night, and never told me where we were going. I loved it. It made me trust him, too, because I figured he would give me a heads up if I ever needed to wear something different than the normal dinner/drinks outfit. I think for guys it’s even easier. You just need to be comfortable in what you’re wearing so you can be yourself. That said, here are some other dating dress code don’ts: flip flops (unless we’re at the beach), jeans tighter than mine (unless it’s Halloween), and cut-off sweatshirts (unless you’re Bill Belichick). You can never go wrong if you come straight from work to the date in your suit or if you rock a button-down and jeans.

IT'S NOT WHAT YOU WEAR, IT'S HOW YOU WEAR IT

I’m a pretty low maintenance gal and I tend to like pretty low profile guys. Of course, it took me 10 years to figure out that there’s a problem if your man has more shoes than you. But hey, better late than never, right? After being with said guy for said amount of time, I’m now hoping to find a man who doesn’t care if we miss the Barneys Warehouse sale.

I like shopping, and I like a man who appreciates nice things, but I once dated a guy who owned practically the entire Ralph Lauren catalogue. And I’m not just talking about clothes. He had the furniture, bedding—everything. If that wasn’t enough, he would only eat at the best restaurants in town and would refer to one of my favorite Italian places as “good, 'cause it’s so easy and cheap.” Guess what—it isn’t so cheap. My point is, whether you’re in Gap or Prada, I could care less. If you carry yourself with the right amount of self-confidence and humility then now we’re talking.

GUYS, ABIDE BY THE GROOMING SYSTEMS

I got this very thoughtful text from a guy just a few hours before we were going out on a date:

I thought that was pretty cool of him to ask. Lucky for him, I don’t mind a beard, some scruff, stubble, or even a little chest hair. Ahem, I said, "a little." What you should take care of before a date is back hair. Ask my younger brother, Brian, and he will tell you I am very vocal about how un-cool it is to see back hair creeping out from the neckline of your shirt. Mad props to him for finding a beautiful girlfriend who embraces it; Tiffany, we love you. For the rest of you dudes out there with this issue, there’s waxing, laser, and an assortment of at-home remedies. Just please deal with it before date night.

LAST BUT (DEFINITELY) NOT LEAST

Never underestimate the power of a compliment. A few words about how nice your woman looks go a long way. You don't need to fawn all over her, but you’ll get a lot more out of your woman (and no, not even like that) if you tell her how great she looks. Don’t assume she knows how you feel—tell her!

Bonus points if you notice something different than usual, or use a word other than "nice," i.e. you look "sexy," "magical," or "did you come here directly from a rap video?!?" (ok, maybe not that last one). Or try this: "You look stunning in that dress." Or: "Your hair looks extra long and shiny today." Seriously, try one of those and let me know what happens. I know we’re just talking dating here, but my Dad always says, “Happy wife, happy life.” Or wait, is that my Mom who says that?

Next week: Jamie shares tips for getting your bachelor pad ready for a woman to come over. 

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