Adventures of Natty Boy & Utz Girl: Wing (Wo)Men

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Meet Natty Boy and Utz Girl: two twenty-something singles dating in the “Greatest City in America!” Since I’m a lot less single than I used to be, and generally, happiness and the internet don’t go hand in hand, expect some regular updates here and on Twitter from NB & UG.


utz girl—

When the leaves change color, I always get optimistic about love. Maybe it’s the fact that more people are around the city on the weekends, packing the bars instead of the beach. Or maybe it’s my brain realizing I need to find a snuggle buddy for winter. Something in the air makes me believe I can fall in love anytime, anywhere.

That air also brings allergies and sinus infections.

So, instead of heading out with my wing woman by my side for my assignment, I snuggled with a box of tissues and chicken soup. Hello stuffy nose. Goodbye fun weekend.

Luckily, I didn’t need to go out this weekend to write this post. I could write a novel with my wing woman stories – the good, the bad and the ugly.

I have friends who will approach any guy I say is attractive – anywhere we are – and say, “Hey, my friend thinks you’re attractive. She’s great. You should talk to her.” Although that opening line reeks of the infamous How I Met Your Mother’s “Have you met Ted?” approach, it generally works. Some people just need the confidence – and approval – to start the conversation.

My group of gals and I have it down to a science. Here’s what we do:

  1. Scoop out the situation. If you’re at a bar or event, wait a few minutes before you start your wingwoman process just to make sure the guy/gal doesn’t have a significant other in the bathroom or around the corner. Approach when you believe it is safe to say they are single.
  2. Brag. It’s your responsibility as the wing person to talk up your friend as much as possible. You know he/she is all that and a bag of Utz chips – so spill it. (Don’t literally spill the bag of chips!)
  3. But don’t go overboard. I have a friend who tells guys that flirt with me that I’m the best person she knows (awesome!) and if he hurts me, she’ll hurt him (um, just met him 15 minutes ago… #toosoon). Surprisingly, most guys are not scared by this.
  4. Be the eyes and ears, not just the wing. Once you set your man/woman free, your job isn’t over. Keep watch over your friend. Start conversing with the others around you – get some info about the guy/gal your friend is talking to.
  5. Have an exit strategy. If the conversation is headed south, you both should have a simple sign – itching your nose or tapping your fingers on the table – to let each other know you need to leave. This is CRUCIAL because being trapped in a terrible conversation is the worst.

Stay charming,

Utz girl


natty boy—

The Wingman. A single guy’s best friend. A truly selfless individual who’s willing to put your needs before his own… well, ideally.

There’s 2 main types of wingmen:

The Single Wingman

I’ll start by saying this is not your best option – but it’s probably the most common. When your wingman is single too, you are in turn are also acting as HIS wingman. This can bring in undesired and unintentional competition. Whether or not you want this to happen, girls will compare you to one another by looks. If you are on the short end of that stick (which I find I often am), this setup won’t bode well for you. BUT – all cons aside, it’s still better than going out alone. Best case scenario, you can meet a couple of single girls out doing the same thing. It’s a bummer if one of you meets someone and the other doesn’t because you leave your friend hanging by the wayside. But hopefully it works out for one of you, and the other friend can take pride in being an accomplished wingman. Another desirable scenario is both of you striking out, and then you can just get drunk together, get some late night pretzel dogs, and pass out on his couch watching Billy Madison on TV.

The Dedicated Wingman

This man is a true hero. He’s already in a committed relationship, and his SO has unleashed him for the evening. For all intents and purposes, his dick is your dick (not in a weird way). Any female attention he receives is subsequently redirected to you. This is a win-win scenario for both of you. You get a dedicated sidekick to help you meet girls, and the wingman gets a night out with his friend and some healthy time away from his girlfriend or wife. He is also in a unique situation in which he can act with almost no shame or regret. He can put himself in awkward situations with girls on your behalf and not really care, because at the end of the night he gets to go home to his girl and forget about it.

The Dedicated Wingman serves 2 primary roles. The first – to hype you up. A 1-on-1 convo with a stranger at a bar can go stale real quick. But with a wingman, you should never run out of things to talk about. He can tell funny stories about you and work to engage her in your conversation. It gets a bad rap, but I think having a 3rd wheel is great – especially in this situation where he’s working for your benefit. The other role of The Dedicated Wingman is the role of the decoy. If you see a cute girl out with friends, the wingman can draw the attention of her friends and get you some face time with her. Better yet, one of her friends will be interested in your wingman, and as shitty as it is, he can string her along all night and maybe convince the girls to keep hanging out after the bars close.

Through all of this though, the #1 responsibility of The Dedicated Wingman is to NOT EXPOSE that he is a wingman! This ruins everything! 1 word — DESPERATION. Are you desperate to meet a girl? Maybe – but don’t let them know that! Desperation is simply unattractive. Nothing annoys me more than than when I’m out with a friend and he goes up to a girl and says shit like “hey see my friend Natty Boy over there? He’s a great guy and he thinks you’re cute”. This has worked out precisely zero times for me. Wingmen out there, please never do anything like this. Let things happen naturally – treat the girl like a new friend and let her make up her own mind about you. It will work itself out.

– Natty Boy


C&D here. What’s so funny about this week’s posts is that UG’s wingwomen do the exact thing that NB says a wing(wo)man should never do! Oh the power of gender roles. Being upfront and aggressive works for the wing woman because it is unexpected, since guys are rarely approached by women. On the other hand, blending in and building rapport instead of being aggressive works for the wingman because the women can let down their guard and don’t feel pressure from a  guy at a bar like they’re used to.

What are your wingman/woman tips?


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