When Did “Trying Too Hard” Become A Bad Thing?

The most politically correct fraternity photo ever: Todd, Scott, and Dennis, 1994

Ladies, meet Scott. That’s him in the middle in the photo. Yes, the one with the mane of hair and the pager clipped to his jeans.

Scott and I were fraternity brothers at UCLA, and for as long as I’ve known him, he has epitomized the term “chick magnet.”

Within the fraternity, there was a standing air of mystification over Scott’s ability to attract women. He didn’t have to say anything, he didn’t even have to make eye contact. The ladies would just magically flock to him.

Seriously, Scott could get shit on by a bird and somehow use that as a way to attract women.

And in case you think I’m speaking in hyperbole here, that is exactly what happened one time….

Years after we graduated, a group of us met up in San Diego, at a hotel bar on the beach. We were sitting in a row along the bar, with our backs to everyone else at the place.

At one point in our conversation, a seagull flying overhead decided to take a great big dump, and it landed right on the back of Scott’s white shirt. Of course, he was a little annoyed. But, being the laid back surfer dude that he is, he simply turned around and wiped it off.

Noticing what had happened, a group of strangers at a table behind us lobbed a few words of sympathy towards Scott. It barely registered in my mind when one of the women in the group got up and walked out of the bar.

Ten minutes later, we were once again deeply immersed in alcohol and had forgotten all about the seagull poop. That’s when the woman who had left returned with a bleach pen. She walked up to Scott and said, “Here, this will take care of the stain.” And before Scott had a chance to respond, she started cleaning off his shirt for him.

Now, in case you were wondering if Scott had been flirting with this woman, he hadn’t. In fact, none of us had spoken a word to this other group. Remember, we had our backs to them the entire time.

And yet, here she was, eagerly de-staining Scott’s shirt for him.

As Scott sat there, watching in mild confusion while this woman wiped down his shirt, the rest of us could only look at each other and laugh in amazement. We were ten years out of college, but Scott’s “talent” hadn’t faded at all. Hey, that’s Scott for you….

Whenever I’ve been down about my dating life, the advice I get from friends usually revolves around the line, “Just go out and have fun. Stop trying so hard.”

And whenever I hear the line about not trying so hard, I’m reminded of Scott. In all the years I’ve known him, I’ve never seen Scott “try too hard.” Because he’s never had to.

So, I listen to my friends’ advice. And I remember all the other clichés:

“Just be yourself.”

“Smile, laugh, have fun.”

“Let the women come to you.”

Well, guess what? I am. I do. And they don’t.

Look, I have no delusions about my own appearance. I know I will never get approached by women with the ease that Scott does. When I’m at a bar, I’m not the guy who turns heads, the guy all the girls are whispering about and wanting to meet. And I’m okay with that. I’m not here to whine about my looks.

But, I also know that because I’m no Scott, I have to do something else to make myself more visible to women. If I want to meet someone, I have to be the friendly one. I have to say hi first. I can’t sit at the bar and play the brooding, mysterious man. Or the shy, quiet guy. Because I’m not hot enough to get away with that.

Having a friend like Scott is a constant reminder that I have to try hard. And that’s why I get annoyed when people tell me to stop doing so. I mean, when did trying hard become such a bad thing? When did effort become a stigma?

We don’t tell a dyslexic kid to stop trying so hard, and to just relax and let the words flow from the page into his brain, do we? We don’t tell a fourth grader struggling with her math homework to stop trying so hard and just let the answers find her, do we?

"You're studying too hard. Don't worry about the test. Make the test worry about you!"

So why do we tell a guy who’s trying to meet people to stop trying so hard?

The answer, I believe, is that “trying too hard” has become a euphemism for “creepy desperate.”

When I’m out, I’ll often take every opportunity I can to start a conversation with someone. I don’t go out to bars hoping to meet the woman of my dreams or even to get laid. (Honest!) But, I do go to meet new people. That’s me “trying too hard.”

At the same time, if she doesn’t seem to be all that interested in talking to me, I say, “it was nice meeting you,” and move on. I’ve learned not to dawdle, not to force the conversation, and not to make her uncomfortable. Because I’m not creepy desperate (well, not yet, anyway).

It’s a fine line, but I think it’s an important distinction that we have to make.

Lavishing her with praise and telling her she’s the most beautiful creature I’ve ever met and insisting on buying her a drink even after she’s turned me down? That’s not trying too hard. That’s creepy desperate.

But going around and talking to people and making sure that I don’t just hover within my bubble of friends when I’m out? Call that “trying too hard” if you want. But, honestly, I don’t see the problem with it.

To me, telling someone that they’re trying too hard is a little misguided, because the problem isn’t trying too hard. The problem is trying inappropriately. So, why not point out how a friend might be making people uncomfortable, instead of launching into the “stop trying so hard” cliché? Because clichés just don’t help.

And for the non-Scotts who do have to try hard? I say go for it. Take every opportunity to approach someone and say hi. Be friendly and warm. Be witty and funny. But remember the fine line between trying hard and creepy desperate.

And, if all else fails, Scott says he’ll hook you up with a seagull rental joint that’s done wonders for his dating life.

Your ultimate seduction tool



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By day, I engineer happiness at WordPress.com. By night, I am a relationships and comedy writer, which can be redundant or an oxymoron, depending on your perspective. I am the creator of Musings, the blog you're reading right now, and LemonVibe, an anonymous relationship advice site. You can also find me on Twitter (I am not the creator of Twitter).

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