There’s an episode from Season 6 of “The Office” where the Dunder Mifflin employees go out for happy hour. Pam invites one of her single girlfriends to see if she and Pam’s boss, Michael Scott, might hit it off. Michael is charming and funny while interacting with this girl; the conversation is easy, the laughter genuine, the friendly interest mutual. Basically, it’s a perfect example of a great non-date—until Michael discovers that Pam invited her friend specifically for him to meet.
Suddenly, the truly likeable Michael Scott disappears, and we meet his alter ego, Date Mike—a guy who tries too hard, wears his Kangol hat backwards, and “playfully” insults his date (a strategy better known as “negging” to those of you who watched “The Pickup Artist,” VH1’s dating reality show from 2007). Ultimately, Date Mike is an embarrassment, and his new flirting strategies don’t go over well with Pam’s friend.
Two thoughts come to mind upon reflecting on Date Mike’s humiliating behavior. The first is, “Why did VH1 cancel ‘The Pickup Artist’ after two seasons? That Mystery dude was hilarious!” This is followed by, “I know what it’s like to be Date Mike.”
I used to have a difficult time making conversation, particularly when talking to a guy I’d just met. I never tried to purposely alter my persona; it just kinda happened. And you’d think that the girl version of Date Mike would bat her eyelashes a lot, or maybe giggle too much at stupid jokes, or act out some other stereotypically girly mannerism, but that wasn’t my reality. I wish it had been, though; people will usually forgive that kind of behavior, perhaps chalk it up to nervousness.
But I did none of those things. Instead, I’d crank up the sarcasm to nearly unbearable levels and make lame jokes out of everything. It’s entirely possible that some unintentional negging occurred. I’m sure that my atypical flirting style made me seem awkward, maybe even unapproachable, to some people. I can only assume that my actions resulted in being labeled “just a friend” by most guys when I was in college, because I didn’t go on any dates during my single years in undergrad.
So what’s a girl to do? Because truthfully, I am sarcastic, and I like to joke about most things, but I’m also not very good at the aforementioned typical flirty moves. I knew there were more good qualities to my style of communication—I’m a good listener and I like when people share their thoughts on what is most important to them—but I had no clue how to find balance in my style. I wanted some of the nicer traits to shine, but I’d spent too much time inhabiting this other persona.
Luckily, after some trial-and-error, I found a new approach: remove all expectations and instead view conversations as learning opportunities. And I don’t mean that I do this only if I’m chatting up a guy—I participate in all conversations this way. By establishing this one rule, I’m basically guaranteed to always be myself. This method allows me to focus on learning something new instead of worrying whether I should be trying harder to find room for a joke or if I’m coming across as overbearing.
There’s at least one reason “The Pickup Artist” was cancelled after two short seasons: flirting with someone by way of slinging insults, whether done playfully or otherwise, is TERRIBLE advice. But I think there’s even more to it than that: if you enter a conversation with any kind of expectation, you’re not going to be yourself. And if we learned anything from Michael Scott’s situation, it’s that engaging in genuine conversation is a much better way to witness someone’s real personality.
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Megan S. is an associate editor at Dating & Hookup. She's a big fan of pop culture, comedy and essay collections (but just a regular fan of any sport that isn't softball or golf).
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