Wingin’ It

Professional wingwoman Meredith Schlosser, star of the upcoming LOGO
series Setup Squad, dishes about the secrets to dating success.

New York’s real estate world can be competitive, even cutthroat: everyone wants to make the right move and close the deal. The dating scene isn’t much different, according to Meredith Schlosser, VP of Sales at Prime New York and professional “wingwoman” on the new reality series Setup Squad.

A native New Yorker, Schlosser employs a tough-love approach to both business and dating—and gets results, whether it’s a signed contract or convincing a shrinking violet to break out of her shell. This relationship expert has applied her successful strategies to her own life. Though her girlfriend Randi Wishnow, a fashion designer, lives in L.A. while Schlosser resides in Manhattan, the two make it work beautifully despite the distance. (In fact, they were featured as one of American’s most captivating couples in GO’s February 2011 issue.)

Schlosser spoke with GO’s Single in the City blogger Esther Zinn about her coaching techniques, the tricks of the dating trade, and the one thing no lesbian should ever do on a date.

GO: By day, you’re in real estate. By night, you’re a dating coach for hapless, unlucky-in-love New Yorkers. How did you get involved with the show?

Meredith Schlosser: I met a friend of a friend, Renee, who is the owner of the dating service company Wings, Inc. She was looking to bring on a team [of wingmen], and she ended up hiring me to work for her. I was actually “winging” it on my own before I met her, and I had matched up a handful of couples. At the same time, the production company, Westfield, knew about Renee’s business and wanted to turn it into a show. I interviewed with the producers and directors of the show and they hired me. Ten episodes later, here we are. It’s so exciting.

We’ve seen a lot of dating-themed reality shows—the many permutations of The Bachelor come to mind. What makes Setup Squad different from the rest?

We’re not just trying to hook people up; that’s not really the goal of the show. I’m not just dealing with gay girls or gay guys—I’m coaching and helping all different clients. In one episode, I was assigned to a gay guy who was really overweight. He never went to bars because he was too insecure and didn’t think he fit in anywhere. The episode shows me helping him through his anxiety and doing other exercises with him outside of the bar environment, like breathing exercises and roleplaying. The show addresses those psychological things, [and I’m] almost like a life coach. We’re not just concentrating on where he’s going to get laid that night.

You’re a successful businesswoman too: does that help you to be a great wingwoman?

If there’s one adjective to describe my best quality, I’d choose aggressive—or proactive—because I’m always encouraging my clients to make the first move. I think everyone’s biggest fear [when dating] is to make the first step, just walking up to that person. Every client I’ve dealt with on the show is just scared. Rejection happens to everybody. And I said to this a straight female client, so what if you get rejected? Everybody does. Just roll with it. My lesbian friends go to the bar and they just sit there twirling their straw in their drink!

I’ve been that person! I hardly ever make the first move! Maybe you can help me out: is there a good pickup line you’d recommend?
I’m very real, very direct. I say, just go up and introduce yourself. Why do people think it needs to be so creative or manipulative? What happened to the ordinary way of “Hello, my name is (blank). How are you? What’s going on?” Totally simple. Simplicity does it.

Were you ever paired with a client so socially awkward that you thought about throwing in the towel?

No, I love a challenge. I think that’s where my strengths come in, being aggressive and proactive. I’ll say, ‘you seem pretty socially awkward and that’s something we need to work on!’ It’s all about getting people to a place where they know what skills they want to work on. My job is helping them get to that point. It’s definitely tough love—but not in an abusive way!

Is there a difference between working with a straight client and a gay client?

I don’t really try to identify sexuality as the main factor in my approach. I try to step away from that and I think that’s what comes through in the show—that love is love and it’s really about the individual. More important than whether somebody is straight or gay is getting him or her to be honest with me.

What’s the most important impression to make on a first date: good manners, good conversation skills or good fashion sense?

All of those things! Good manners is number one. Looks aren’t everything and brains aren’t either. I think we’ve all been in that situation where the girl’s really attractive, but she can’t spell her own last name. I think everyone is taking it to the next level in social media these days, and human interaction is becoming rare. People are so preoccupied with their cell phone, texting, whatever. When you’re out on a date, put that cell phone away, cut the crap! What do you think is the biggest mistake lesbians make on dates?

I’d say dwelling on something from the past. My friends will go one dates, and afterwards will say, “this girl just talked about her ex!” Just leave it alone!

Oh yes, the TMI: everyone’s favorite method of oversharing. On another note, does astrology make a difference in girls’ compatibility? What’s your sign? I’m an Aries.

I’m a Cancer, and my girlfriend is a Scorpio. If you Google our compatibility factor, we get four out of four hearts! All I know about Aries is that they’re kind of bossy.

We’re “proactive!”

My first heartbreak was an Aries. It’s okay, I won’t hold it against you.

Let’s talk about your current relationship instead: we’re introduced to your girlfriend Randi on the first few episodes of the show. Did you have any first-date jitters?

Long story short, a friend of Randi’s and I started talking [on an online personals site] and became friendly but nothing came of it romantically. I always thought Randi was extremely sexy  in pictures with her friend, but I knew she was in a relationship at the time. Almost a year passed…Randi had broken up with her girlfriend, she was going to be in New York on business and wanted to meet me. We spoke on the phone while she was in town and decided to get drinks together the next night. Our connection was absolutely magnetic.

So who made the first move?

We were out for drinks on our first date, sitting across from each other at the table, and you could cut the tension with a butter knife. I adjusted my jeans by my ankle, and as I brought my hand back up to the table, I slowly brought my hand up along her leg and left it there for a second. Then I moved away to see her reaction, and she replied with: “you should put it back.” I was intrigued because I’ve always been the dominant one in all of my relationships, but I swear she had me there!

In closing, what piece of advice would you give for lesbians jumping into the dating pool?

When you’re going on a date, really amp yourself up with confidence. Be the one to lead the conversation, pick the place, ask the questions. Taking control of the situation is very attractive. And don’t have such high expectations of where the date is going–just be in the moment. And, who cares about the three day rule? If you like her, follow up. People don’t respond well to games or B.S., and it’s flattering to be on the other end of that phone call.

“Setup Squad” premiers April 25 on LOGO.

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