Chick Literal Dating Advice From Some Of Pop Culture's Best Wingmen Andrea Greb

This past weekend, events (and friends) conspired that I fell straight into one of those perfect romance movie moments you so often see onscreen and so rarely experience. Imagine, if you will, you’re on a deck in Maine, staring out at a view of mountains covered in freshly fallen snow. You’re sitting in a hot tub, talking with the cute guy who’s been laughing at your jokes all weekend about your mutual obsession with New York City, and the stars are just starting to come out. Stars, you think, that seem to be aligning in your favor for once. The minutes tick by…and suddenly your friend’s husband is opening the door to the patio and informing you that everyone’s leaving in ten minutes, and you’d best get ready to go.

“If you were waiting for the opportune moment, that was it,” a voice in my head said as I went back inside. The voice, of course, belonged to one Captain Jack Sparrow, and he was entirely correct. Dammit, Sparrow, I thought, where were you 45 minutes ago? Why hadn’t I listened to him earlier and just kissed the guy, instead of letting my inner monologue about rejection and awkwardness win out?

This is why wingmen are key. They’re looking out for your best interests, but are going to share in none of your shame. They can encourage you to do the brave thing because they don’t have to deal with your internal turmoil about how weird things are going to be if you don’t succeed. Real life wingmen are key for getting you into appropriate situations. However, at some point you’re going to be on your own, which is why I suggest shutting off the voice in your brain telling you you’re about to look like an idiot, and instead taking the advice of some of my favorite wingmen:

Anna, The OC. I hate having to classify Anna as a wingman because I was always rooting for her over Summer, but I can’t discount her abilities in the advice-giving department. “Confidence, Cohen” is short, sweet, and perfectly to the point when we just need something to calm our neuroses and remind us that if we just believe in ourselves, it’s going to be okay.

Barney Stinson, How I Met Your Mother.  Barney’s skills as a wingman are legen - wait for it – dary.  (Seriously, the “Haaaave you met Ted?” line works in real life if your friend’s name is Ted, and also works if you substitute the name of the person you’re actually trying to introduce.) My favorite bit of his guidance is a simple one – “Suit up.” I think this is about way more than clothes (though a well-tailored suit does look great on pretty much everyone). Suiting up is about showing up everywhere, be it a job interview to a casual night at the bar, looking great with your game face on. Suiting up is about being prepared for the fact that any moment can turn legendary, if you let it.

Cameron, 10 Things I Hate About You. While Cameron was only wingmaning for Patrick for his own ulterior motives, it doesn’t make his advice any less sound. “You embarrassed the girl. Sacrifice yourself on the alter of dignity and even the score.” While we don’t all have access to a marching band and the skills to carry off a song and dance routine, the point remains. Dating isn’t always dignified. Sometimes we have to be willing to take the risk of looking a little goofy.

Rachel, 500 Days Of Summer: Wingmen are meant to push you in the right direction, and sometimes that’s away from the object of your affection. Rachel proves that sometimes your sister is the only wingman you need, with gems like “Just because she likes the same bizarro crap you do doesn’t mean she’s your soul mate.” and “I know you think she was the one, but I don’t. Now, I think you’re just remembering the good stuff. Next time you look back, I, uh, I really think you should look again.” These are all wise words, though I’ll be honest – Chloe Grace Moretz is awesome and I would probably follow any advice she gave, regardless of content.

I’m filing away all of this advice in my brain so that the next time my real life wingmen are back inside the house, giggling and wondering whether or not anyone’s going to make a move, I’ll have other wise people reminding me not to let the opportune moment pass me by.

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  1. I heard someone say once that Mercutio (in Romeo and Juliet) was one of the best wingman in all of literature; He basically sees that Romeo is in the dumps over Rosaline and not only pokes light-hearted fun at him to weaken the tension, but he calls him out again when Romeo magically falls in love again the next day. Basically, he’s like, “Romeo! You totally left us hanging last night, bro,” and Romeo’s all, “No, I fell in love! I fell in love and that makes it okay.” And Mercutio is all, “…Nah, bro. What, did you see another one of your strumpets again? Did her eyes shimmer and her hair gleam like scarlet waves? Was it true love? WAS IT?” And Romeo tries to defend himself, and he’s like, “You, stop being silly. It was love at first sight!” And Mercutio goes, “Nah, man. You fall in love, like, every 3 seconds. Chill, dude, just step back for a sec.”

    And that’s the story of Romeo and Juliet, a.k.a. “Mercutio: ‘This Guy is Crampin’ My Style, But I Love Him Like My Brother, Yo”.

  2. And Rachel also gave this awesome line: “Just don’t be a pussy”.

  3. Great Article! :)

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