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

  1. Ah… 1994 Dennis was a cutie !

    “if she doesn’t seem to be all that interested in talking to me, I say, “it was nice meeting you,” and move on.”

    That is not my idea of trying too hard, that is my idea of trying just the right way. Don’t change ;)

  2. You also forget about accentuating what you have that women do find attractive- a man that can dance is quite the turn on!

    • Well, I AM trying to branch out a little bit, ya know. I can only date so many women in the swing dancing scene before it starts to feel kinda awkward, given that we all see each other at the same venues…. ;-)

    • Not gonna lie, I love meeting women through dancing far more than introducing myself and starting a conversation… granted, my dancing is a mix of high energy hip-hop/stripper/salsa/grinding but when a girl is willing to throw down with me I know we’ll learn more about our compatibility in those first few moments of dancing than in 30 minutes of conversation.

      My favorite moments with women I’ve dated/hooked up with have been those in which few-to-no words were spoken upon first meeting, where all communication took place in body language and eye contact. Being able to sense such strong chemistry with a woman without actually having a conversation is a huge turn on to me.

    • It also tells a woman a lot about a man- if you can lead me, and make me look good, instead of looking like a fool, then I have hopes for what else you can bring to the table! Dennis, just branch out to new venues ;)

  3. “…because the problem isn’t trying too hard. The problem is trying inappropriately.” Exactly! I love how people will offer their opinion but nothing REALLY helpful. :)

  4. I’ve never understood why I had so much trouble. I mean, I’m a tall, reasonably attractive guy without a speech impediment or rancid B.O. It doesn’t seem like I should have to try very hard, but for the most part women do not just approach me. I don’t feel like I should be the Omega Male within my group of friends, yet there I am. I constantly see girls approach friends of mine who are less tall, less smart, less funny, and less good-looking than I am. It used to drive me nuts trying to figure it all out.

    My own conclusion: Some guys will simply never attract an acceptable mate. That’s right, some of us really will be alone forever, and by your 30s you should have a pretty good idea of whether you’re one of them or not. It’s not her, it’s you. I don’t know why, but it’s you, just like it’s me.

    But that’s not so bad, really. The way I see it, most relationships are bad ones. Almost all of them end in a split. Of those that don’t quite a lot of them are made up of two miserable people who are more or less stuck with each other. Hell, that describes at least half of the marriages in my family and among my friends.

    Try, don’t try; be confident, feel like a loser; dress well, dress like a slob; be nice, be a prick. None of it matters at all. Women will still see you as a great friend.

    • “Quit, don’t quit; noodle, don’t noodle; you are too concerned with what was AND what will be! There is a saying: yesterday is history, tomorrow is a mystery, but today is a gift; that is why is called the present!” – Master Oogway (a.k.a The Crazy Old Turtle), Kung Fu Panda.
      Sorry, your last paragraph just begged me to quote this… :)

      Ahem, anyway, onto the actual reply: this is a pretty sad post, and I’m sorry for your not-too-great experiences with women (and your avatar dude, he’s just so appropriately pathetic ;) ) BUT, not being a chick magnet (by the way, thank you Dennis for that perfect picture) is not actually a bad thing. Now, mister C. Munroe, I won’t try to discover what’s “wrong” with you that women just don’t fall in your lap, because I don’t know anything about you, but I DO know quite a lot about me, sooo, I’m going to try and make that information relevant to this.

      I LOVE beautiful women. Or better said, I love women’s beauty: I love smooth skin, shapely curves, seductive fragrance, eyes in which you want to drown; wit, sweetness, kindness, tenderness, courage, strength; I love seeing them smile and hearing their laughter and holding them while they cry. Nonetheless, of the MANY beautiful women I’ve met, the ones I’ve tried to get intimate with are less then a fraction. I don’t why, it’s just that as much as I may lust after them (and boy, do I lust…), I’m just very pretentious (trust me, not by choice). I need a spark, a natural AND mutual attraction for me to try anything with a woman (romantically speaking), and after that I need to nurture that spark into a reasonably steady flame before I try to get intimate with that woman. This is true whether I’m aiming for a stable relation or just a few nights of kinky erotica – it’s just how I am. So that’s why I’m not trying too hard. I don’t know how much this applies to others, but maybe somebody will be able to relate to it…

      I agree with you on your view on relationships – I’ve had the same experience. Nonetheless, I still yearn for that special relation with a women, and I don’t think I’ll ever give that dream up – it’s just too sweet…

      “Women will still see you as a great friend” – yeah, that’s all good and nice, but how about seeing me as a great LOVER?! Now don’t get me wrong, I DO have an unreasonably* amount of confidence in my skill at the pillow game; it’s getting the women into a situation that allows me to prove that skill that’s problematic!!!
      *Unreasonably = I have quite a lot of confidence, but not enough witnesses to justify said confidence beyond the shadow of a doubt, and the strongest of those witnesses, with the largest amount of experience regarding the afore-mentioned skill, is my right h… uhh, what?

      Ahem, moving along…

      Well, MY conclusion is that you HAVE to work hard at it, whether is meeting new people or just keeping the ones you’ve already met, it’s just that if you naturally like each other, the work doesn’t seem so hard anymore… (someone said something similar on this site but I forgot who or where, sorry, I’m not plagiarizing).

      That being said, I completely agree with Dennis: it’s not trying hard that’s bad, it’s trying inappropriately – spot on doctor Hong! (hey, that kinda rhymes!)

    • @Andrei B. – Buddy, not “an unreasonably amount of”, but “an unreasonably *something* amount of”, or “an *unreasonable* amount of”, get it? I suspect what you were trying to say is: “an unreasonably large amount of confidence”. But I forgive you, it was late and you were probably tired… :)

    • Dude, I feel ya. But honestly, that’s why I’m so big into evolutionary biology and psychology. I feel like it gives me insight into female behavior. Seriously.

  5. I think the whole “trying too hard” is a way to say that your true personality is not showing, and they can tell that it isn’t showing because the personality that IS showing is not who (whom?) they have grown to love and care for… IMO.

    • But what if you’re naturally introverted, like CM? I think the problem is that, the way our society is set up, natural introverts have a much more difficult time getting noticed and attracting the opposite sex. So, if they want to do so, they simply HAVE to pretend to be extroverted.

    • I don’t think they have to pretend to be extroverts… there are people who are MORE attracted to introverted people. If it’s to the point of social anxiety, then they definitely need to deal with their fears as they are keeping these people from forming important relationships. If someone is like CM where they just need to feel more comfortable before they open up then they just need to put forth some (some… not too much and not fake) effort into building the relationship until they have both reached their comfort level. It isn’t about pretending it’s about working with what you have and recognizing that neither extreme is going to help you.

    • True. I totally agree that there are people who are more attracted to introverts. To me, though, the problem is that it’s a numbers game:

      If you’re an introvert, you’re simply going to meet fewer people. After all, if you prefer to be by yourself, then you’re not gonna be hanging out in places with tons of other people around. So, your chances of coming across a like-minded individual will be much slimmer.

      Then again, maybe that’s what online forums are for…. ;-)

  6. Yep. I’ve often said that extroversion is the absolute most valuable character asset for a single male in the dating world. It seems a little unfair, but being extroverted attracts people and being introverted, well, it doesn’t actually repel them but it’s not at all alluring in a romantic sense.

    And I can’t fake being extroverted. When I try, it looks like trying too hard. When I don’t, I come off as aloof.

    And while I love women’s beauty, I’ve lived long enough to know that the beautiful ones are not better people than the not-beautiful ones. It’s one of my own faults that I’m still shallow enough to consider being physically attracted to someone an absolute requisite in a potential partner.

    I need a spark too. I don’t just fall for any pretty girl with whom I make a connection. Unfortunately, the times I’ve felt that spark it hasn’t been mutual. I lose.

    And I’m tired of losing. Like literally tired. Just thinking about it makes me want to go back to bed. I don’t have the energy to try anymore. Maybe it is hard work, but I resent the fact that I’m the one expected to do all of that work simply because I possess a Y chromosome. I like equality in my partnerships.

    So I’m not trying anymore. I’m not saying I’ll never date again, but at this point it seems like all risk and no reward, and there are more pleasant things I can spend that energy on.

    • Considering physical attraction an absolute requisite in a potential partner is not a fault (well, as long as it’s not the *only*, or the *main* requisite). Rather, it simply means you’re not (too) old. Don’t worry, eventually you’ll get there, no need to rush it… :)

      I second your choice with regards to dating (err, click the like button? Give you a thumbs up?). Dating should be fun, not stressful, and definitely not a chore. There are definitely more pleasant things you can spend that energy on. After all, *not dating* doesn’t mean *not living*. Maybe now that you’ve escaped the stress of having a (bad) dating life you can focus on all the good things in life that you might have missed while desperately searching for a mate.

      I cannot get the “too tired” thing. Mainly, because I don’t “date”, per se. If I really like someone, I try to go out with her. If I succeed, good, if not, that’s also fine (if a bit disappointing). Further, if I do get a date, I don’t bother myself with it’s outcome – whether we’ll get to become friends, share a passionate one night stand, become life mates, or end the date in a platonical way and never see each other again, I don’t worry about it, all I’m interested in is enjoying my time with her. If I feel that there’s a lot of potential for us to naturally grow closer to each other, then I will work towards it. However, if she likes me, then she’ll work towards it also. Otherwise, there’s no point investing your time and energy in someone who’s just not interested. Of course, if you work hard enough, you might succeed in seducing her, but I feel that that kind of behavior is for a trophy hunter who feels that he’s just got to nail each and every women he comes across.

      Also, not dating a woman and just being friends with her means you can just enjoy her in all the ways you couldn’t if both of you were under the pressures of a romantical date (you know, all that trying to impress/seduce each other, the fear that you’ll fail, etc.).

      P.S.: I LOVE the contrast between your avatar as “anonymous” and the one as “C.Munroe” :)

  7. Crap, it’s Munro, not Munroe. *sighs in resignation* No perfect typing for the wicked…

    Guys, I kinda sorta have to side with Dennis on the introvert thing. While I don’t agree that introverts should force themselves to become extroverts (or even worse, fake it), there’s always room for a little self-improvement. If, say, you’re socially awkward, you can try, for example, learning how to make jokes (yes, it is a skill that can be learned, to a certain degree ). Sure it’s hard work, but it’s totally worth it: not only will you be able to handle other people’s company easier, but that will help you to loosen up and enjoy THEIR company!

    Like Nikki said, it’s all about your personality, and while you don’t have to be an extrovert, you do need to make a little effort. After all, other people (and potential mates) can’t like you if they can’t see you (or if instead of the real you they see just a loser desperately trying to impress and making a fool of himself in the process)! And if the real you is a creepy pervert with bizarre hobbies, then… boy, you’re SO screwed ;p

    • It IS all about the personality ! I can’t speak for all women but in my case, attraction is definitely something that starts on a mental level. Many things about a man’s personality can completely make make us go from neutral to super-attracted.

  8. When I bitch to my friends that dating is sucky, they tell me that maybe I should take break. And when I bitch that I’m lonely, those same friends tell me I should make more of an effort to date.

    Thanks, friends.

  9. Perhaps you should just go shirtless all the time, Dennis. HOT.
    ;)

    A) That picture is priceless
    B) The difference between trying too hard and being desperate is sometimes a fine line… but as you pointed out so well, there IS a distinction there. There is nothing wrong with trying, but just try not to come off as that psycho who’s going to cyber stalk you and show up at your house in the middle of the night singing love ballads.
    C) It sounds like you’ve gotten a pretty good handle on all of this. Looking forward to the next article: “How Trying Too Hard Landed Me A Fabulous Woman” :)

    • Haha, thanks. I get weird looks from people when I do that, though, especially at fancy restaurants and libraries and such….

      What if I showed up at her house in the middle of the night singing Monster Ballads? Come on, a little Whitesnake or Poison has to melt her heart, no?

      And, yes, I sincerely hope that is the topic of my next article….

  10. I dunno what happened to the guy on the left, but he looks pissed. Anyway, If all fails, just hitting in the back of the head with a baseball bat. That’s how the Cavemen did it, right?

  11. Well, I am gonna add my 2 cents..or maybe its up to like 5o cents with inflation…anywhoo, I am a very extroverted female and even I get told I am trying too hard. And I actually LIKE introverted guys, unfortunately, maybe its their lack of being able to express themselves or maybe not, but it seems they don’t like ME. Then it makes me feel bad or self conscious for scaring them off by being “too much” . Or they never make a move because maybe the figure since I am outgoing I am going to do it for them? And I feel even more self conscious that they don’t like me and I wonder what I did wrong. I still want a guy, no matter HOW SHY, to ask me out or at least make it REALLY OBVIOUS that he’s interested…I guess extroverts aren’t good with subtlety? Which of course doesn’t happen. So I guess my point is, be yourself because dating really is a numbers game…And Dennis on behalf of the Def Leppard drummer BAD DENNIS! Not nice! ;)

    • Introverted guys have no idea how to ask girls out. It gets even harder if the girl is very out going with lots of male friends. I’m pretty introverted but my job has forced me to become extroverted and that’s what I see when I hang out with my introverted friends. A girl could say “That was so funny, would you drive me home” and the introverted guy would just strung his shoulders and go “oh I don’t think you live near me”. The best way and this is what I told a really out going girl when she couldn’t get my friend to ask her out. “Don’t wait for him to say something. You invite him out on a date and tell him you think he’s cute and make sure you do it one on one no one else around.” She did that and they are still dating almost a year later. Introverted guys often have low self confidence remember that. Sorry I type a lot.

    • I think you are right. If you want to meet someone you have to be out there more and try to talk to people. I’ve spent most of my life not being able to talk to people because of self confidence issue but now I just try to talk to any girl I think I might have a connection with. I find that if I go to a bar (I hate clubs) I might talk with 10 girls and get one or two number and from those numbers I’ll follow up with like 2/3 and from that a date from like half and from there it just keeps going. Still it is a number game. So talk and enjoy and be yourself because if that girl isn’t into you. There will be another. Also please remember two things, smell good BO is BAD and try try try to be relaxed. At first it’s hard but it gets easier.

  12. it is very hard for me to meet a decent woman today. i go out to the clubs on the weekends but i always seem to meet all the trashy women instead of the good ones.they play games a lot but i am not into that.i consider myself an average good looking straight man and i never thought that i would have this problem.where are the decent straight women today for us good straight men?

  13. I think there’s a fine line between trying to find someone, and truly “trying too hard” in a manner that would tend to scare away a potential love interest. It’s a difficult line to balance at times, especially when you really, REALLY would like to meet someone and when you finally do start to hit it off, its been (possibly) such a long, exhausting process you want to do everything you can to make sure it works and keep the other interested. This situation, IMO, is where it can ewasily cross in to “coming on too strong” or “moving too fast” before you even realize what you’re doing, and can (and often will) blow right up in your face.

    The only advice I would ever have for these situations (since, even looking back, I’m not sure how I would have avoided them), is to just learn from your mistakes. For me it was just a trial and error process, and now that I know most of these pitfalls and what to look out for, its a lot easier to pick up on when things might be going slightly askew, and how to adjust on the fly in order to avoid some of the mistakes I may have made in the past.

  14. Hey dude, just stumbled onto your blog via the Cracked article about poker. I enjoy your writing style. My whole thing with meeting women in bars was having some sort of distinguishing feature to get attention. Long hair, different style of clothes, whatever. . A little bit of peacocking never hurt anybody. Well, that’s not necessarily true. You will get just as much shit from other dudes as you will get attention from the womenfolk, but the bottom line is that YOU are getting attention automatically, instead of working for it. Just a thought. Keep writing. It makes for a pleasant saturday morning hangover read.

  15. I’m another one who found this blog via your Cracked article (which was itself a long shot as I’m not interested in poker at all — just very interested in reading about how reality can be different from perception!) You have a way with words, and you have really captured the dilemma of the non-superstar guy here.

    If I can generalise what you’re saying slightly, I think a very similar thing applies to women who aren’t conventionally beautiful. Just as a “beta male” guy is forced into the difficult position of having to try hard *but not too hard* to get some attention, and runs the risk of being considered “creepy” if he tries too hard, a “beta female”‘s main option is to act and dress more provocatively — but if she goes too far she’ll be considered “slutty”.

    I guess what I’m saying is that I think the really important distinction is between sexually-powerful people (of both sexes) and sexually-not-so-powerful people. I naturally envy men and women in the first category, and feel solidarity with those in the latter!

  16. I think you’ve kind of missed the linguistic point of the cliche, but you’re right that people misrepresent the process of meeting people. Pushing your comfort zone and acting as you describe is trying. Being creepy desperate is still trying, but it’s trying too hard.

    Another Cracked follow-up here too.

  17. meeting good women is very hard today. as a straight man, i go out a lot and i seem to meet all the nasty ones instead of the good ones. why? i do not know. they do dress like pigs, especially the way they act. half of these women, are not worth meeting. i was married twice, and i was a very caring and loving husband at the time. they both cheated on me, and i never cheated on them. i am sure they had the word whores, written on their foreheads. but i could not see it at the time. this gives me a very good reason to be bitter about women, as you can see why. we have a lot of filthy lesbians out there now, which adds to the problem as well. these women are a disease. i am sure a lot of you men feel the same way i do. how much more can we be hurt?

  18. it is very true that a lot of women have become very trashy today. what pigs they turned out to be. to meet a good straight woman has become very difficult for us good straight men now. there attitude sucks, and trying to start a conversation with them is very impossible as well. i go out a lot myself, and always seem all the nasty ones instead of the good ones. then they wonder why us men have a bad attitude as well, especially when they think that we are just out for sex. i just want to meet a good woman that could make me happy.

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