Brookey's Cafe Blog

TGIF!

So last weekend I met up with a guy friend for movies and lunch. After the movie, we hit a restaurant, grab a table and suddenly up pops our cute waitress. Natalie. She’s pretty – long curly hair, petite frame, nice smile…something about her reminded me of Olivia from Love & Hip Hop – except much younger and thinner. My guy friend, who is married with 2 kids, instantly responds to her…but not in a gawking, jerk’ish way. More like a “If I was single and about 10 years younger” way. Totally innocent…so we decide 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….AGAIN.”

Meanwhile, I’m tickled pink. I think it’s the funniest reaction ever and I can’t stop laughing.

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 oddly enough, 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 is on me and I'm oddly intrigued.

When she brings our food, he says to her, “You didn’t really believe her did you?” She pauses for a second and then says, “No.” There’s another awkward pause and then she skidaddles away again.

Now I’m in tears. For some reason this is ten times funnier than the movie we saw – which was Friends With Benefits.

We eat and forget about the waitress while we chit chat and catch up. As we finish up, he says, “Maybe I should put my work number on the check when she brings it just 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, “Okay…whatever.”

She barely walks away before my friend screams on me, “YOU SUCK AT THIS!”

Now I can hardly catch my breath I’m laughing so hard. I have no idea why I’m finding this so funny, but it made my entire afternoon.

So…that being said, I am the worst wing woman ever in the history of “wingwomandom.” Maybe I didn’t take it as seriously as I should have because I knew he was married and 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 all where I went wrong, and how I can do better next time…with my SINGLE guy 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 or believe anything I said. If I got her to like me, then I wouldn’t have to try hard to convince her of how worthy my male 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 athletic…kinda hard not to love a dude in the NBA anyway.” Okay, so my friend isn’t in the NBA, but lies are okay…the more outrageous the better! I would have said it in jest anyway to gauge her reaction, and my friend is over 6’3 so she probably would have believed me. Then we would have been able to determine her level of interest in HIM, not his interest in her. But by all means, if the friend you’re trying to hook up is GENUINELY interested (and not playing around like we were), then be honest and sincere. You don’t want the target to think you’re just blowing smoke up their ass 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 he really WAS in the NBA ;-)

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’s more interested in me than him. 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 you 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 being a good wing woman, keep in mind not everyone responds well to such personality types. She probably thought I was silly…or creepy, or simply just weird.

5. Lastly, my real mistake was trying to be a wing woman in the first place. It was all in jest, 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.

Anyone have a funny wing man/woman story to share? Anything you wanna add? Go!

-b