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Last weekend I met up with a guy friend for a matinee and lunch. After the movie, we hit a restaurant, grabbed a table and up pops our cute waitress. Natalie. She’s pretty – long curly hair, petite frame, nice smile…something about her reminded me of Amina from Love & Hip Hop. My guy friend, who is single but dating, instantly responds to her but was trying to play it cool. So I decided to have some fun.

“Want me to hook you up?” I ask with a mischievous grin.

He looks at me like I’m about to start some trouble.

“No” he responds in a sarcastic tone that indicates he doesn’t need any help – pimp that he is.

“Aww come on, it’ll be fun. Let me be your wing woman.”

Before he could answer, our waitress comes back and I blurt out, “He thinks you’re cute.”

She gives me this awkward look like she wants to run, but realizes she can’t because she has to take our order. She just smiles and asks if we’ve decided on our meal.

Okay…that was all wrong. He’s looking at me like he wants to strangle me, and then looks at her to see if what I said moved her in any way. It didn’t. We order appetizers and drinks, as we need more time to figure out what our entrees will be, and I can tell she was thinking, “Great…now I gotta come back.”

She comes back to finish taking our order and I notice that now she’s only looking and smiling at me. Even when he tells her his order she doesn’t look at him – not once – but she’s EXTRA friendly with me. Maybe she thinks he’s my date and doesn’t want to offend me? Maybe she thinks he’s funny looking (although some would say he favors Kobe Bryant)? Who knows, but all of her attention was on me. The air around us was awkward and then she skidaddled away again. This was way more interesting than the movie we saw!

Finally we eat and forget about the waitress. As we finish up, he says, “Maybe I should put my number on the check to see if she calls me.” I say why not…let’s see if she bites.

She brings the check and I say to her, “By the way, he’s not my date, we’re not together.”

She looks at me as if to say “Who gives a flying fig” and puts her hands up and smiles.

She barely walks away before my friend screams on me, “YOU SUCK AT THIS!” I start to laugh, but he’s right. I am the worst wing woman ever in the history of “wingwomandom.” Granted, I didn’t take any of it seriously because I knew that he really didn’t want to get with her. But if he DID want me to be his wing woman, let me tell you where I went wrong, and how I can do better next time should I decide to hook up one of my friends.

1. Strike up a real conversations first. I didn’t engage her in any girl talk. I just said “he thinks you’re cute,” so I didn’t even warm her up to me first so that she’d take anything I said seriously. If I got her to like me, then I wouldn’t have to try hard to convince her of how worthy my friend is of her time. I went in too soon, and being too forward can send a target running for his/her life.

I should have just provided positive anecdotes about him in a more non-transparent way – like “Women love him, he’s so sweet and a gentleman.” This way, I can determine her level of interest in HIM based on her reaction, not his interest in her. Just make sure that when complimenting your friend you’re being honest and sincere. You don’t want the target to think you’re just blowing smoke and ruin your friend’s chances at scoring.

2. Make sure the target is single. She could have been engaged or married for all I knew, even though I didn’t see a ring on her finger. But if she’s booed up already, then nothing I say would make her give up the digits….unless she’s a cheater.

3. Make sure the target is interested in men (or whatever sexual orientation the friend you’re hooking up is). Once our waitress started paying more attention to me, my friend joked that maybe she goes for women. It never occurred to me that she might be a lesbian…and after all, I AM cute! Oh, and if you find that the target is more interested in you than your friend, then back off. A good wing man/woman has to be trustworthy.

4. Another mistake I made was not assessing her personality correctly. She seemed a bit shy, so my outgoing nature probably freaked her out. While being extroverted is probably the trait you need to be a good wing woman, keep in mind not everyone responds well to such personality types. She probably thought I was silly, creepy, or just plain weird.

5. Lastly, my real mistake was trying to be a wing woman in the first place. We were having fun and no one took it seriously – but if a friend asks you to cut it out, don’t go trying to hook him or her up without their permission. It’ll just be awkward for all involved, and they may be embarrassed or resent you for putting them in a tight spot. If they truly want you to hook them up, they’ll let you know and give you the go-head, smoke signal, code, whatever. Don’t take it upon yourself to be a wing man/woman – it’ll just end badly. Find your OWN target.

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