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A Professional Wingwoman on How to Hook Up Your Girlfriends

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Wingwoman Girlfriends Bar

Are you growing tired of your best girlfriend cancelling on great plans with you and yours because she "doesn't want to be the third wheel”? It might be time to help her meet a great guy of her own. To help you master the art of the hookup we called up an expert wingwoman to show us how it’s done.

Meet Nafeesa Saboor, social butterfly and queen of the side hustle. After helping her friends break the ice for free, it occurred to her that she could (and should) be getting paid for her services. Nowadays, when she’s not blogging about “lifting your spirits” on her blog Shoes N Booze or working as a PR consultant, Saboor moonlights as a professional wingwoman whose job is to help get her clients a meet and greet with that cute guy across the bar. Yes, really! Read on to learn more about her awesome job, find out how she plays cupid, and how you can shoot a couple arrows, too.

ESSENCE.COM: Exactly how does professional “winging” work?
NAFEESA SABOOR: You get paid by the hour. You usually book at a two-hour minimum and you’re clients are booked about a week in advance. Sometimes the women send you a picture ahead of time and ask you what they should wear and how they should look on their first outing. I’m not a matchmaker. It’s more like the idea of going out with a friend who may be a little more social than you are or more outgoing and is able to help you identify people you may be able to connect with, and then connect you with them.

ESSENCE: Is it mostly women that hire you, or do you work for men as well?
SABOOR: So far it’s been mostly women, but the first time I ever went out with anyone it was a man. This all actually started because I was working with men on this, and I kind of told a friend what I would do for my clients when I worked in PR consulting, and she was like, “Oh my God, you should so be a wingwoman.” I was like, hmm, okay. Now, I don’t own the business but I consult through another company. I’m a freelance winger. They call me in to go on wing dates.

ESSENCE: What tips do you have for women who want a lesson in “winging” to help out their girlfriends?
SABOOR: First of all, be alert and aware of who’s around at all times. Don’t just get so caught up in the conversation with your girlfriend that you’re not paying attention to who’s around, who might be cute, who isn’t, and who might be checking you or her out – even who has a cute friend. I’m not saying you have to be working the room the whole time – you can sit in a stationary spot – but just have a clear view of who’s coming and going. Also, you want to be sure the people who are coming and going can see you both as well.

ESSENCE: Is there such thing as going too far, when you’re trying to help?
SABOOR: I think it can be kind of weird if you call a guy over for your girlfriend, because then he may feel put on the spot just a little bit. What I’ve found works is identifying. Say maybe you have two guys or a group of guys together, you have to figure out a way to put yourself in their space – in their peripheral, or kind of near them or in their direct line of contact. Then insert yourself into the conversation or into the space so that they have to start a conversation with you and then you can bring your friend into the conversation. If they’re all by the bar, and you know you need a drink, don’t slide in two people away from them to order your drink. See if you can excuse yourself and go right next to that guy in the group that you want to speak to for your friend. It’s all about strategy.

ESSENCE: Is it tricky to avoid the guy thinking you’re actually flirting with him?
SABOOR: It is. That’s why it’s always easier if they’re in a group because then you flirt with the other guy.

ESSENCE: What are the signs your target guy isn’t feeling it and you should maybe give it up and move on to the next one?
SABOOR: There’s a subtle way that people kind of end conversations that you have to look out for. You’ll know within the first few minutes. If they don’t ask you what else you’re doing, or if they seem very dry in the conversation or looking away a lot within the first few minutes. Also, if you find him flirting too hard with you in particular even though you’re purposefully flirting with his friends.

ESSENCE: If the guy seems really into you, do you end the whole conversation so your friend doesn’t feel uncomfortable?
SABOOR: I think it depends. If you’re a single girl and your “winging” for your friend, you need to let her know before you guys go out where you stand. I say, “Look, you’re shy and I’m not and I’m trying to help you, so I’m going to throw it out there for you. But, if by chance, the guy likes me instead, I’m not going to turn him down just because he didn’t like you. We’re both out here with a goal. Who wants a guy that doesn’t want them anyway? It’s a losing situation from the beginning.

Want more great advice on how to “wing it” from Nafeesa? Find her over at Shoes N Booze anytime or follow her on Twitter here.

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