Dear Wendy
Dear Wendy

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

Guest columnists and contributors are generously sharing their talents and insights while I’m taking some time to care for my new baby. Today’s essay comes from “His Take” contributor, Dennis Hong, who writes about relationships and other topics at Musings on Life and Love.

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 over 15 years ago, 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 — even during the most inopportune times.

Years after we graduated college, for example, 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. One of the women in the group — a woman none of us had even noticed or spoken to — got up, walked out of the bar and returned ten minutes later 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. We were ten years out of college, but Scott’s “talent” hadn’t faded at all.

Whenever I’ve been down about my dating life, the advice I get from friends usually revolves around the line, “Stop trying so hard.” And whenever I hear that, 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. But I’m no Scott. I know I will never get approached by women with the ease that Scott does. 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.

I know that because I’m no Scott, I have to do something else to make myself more
visible to women. 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? 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.”

It’s a fine line, but I think it’s important to make the distinction between the two. Lavishing a woman with praise and telling her how 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 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. Honestly, though, I don’t see the problem with it.

The real problem is trying inappropriately. So, instead of telling someone he’s “trying too hard,” why not point out how he might be making people uncomfortable? Because clichés don’t help, but practical, specific advice does.

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.

*Dennis Hong blogs about the life lessons he’s learned. Check out his
and his friends’ musings here.

62 comments… add one
  • artsygirl October 19, 2011, 12:20 pm

    Great story and wonderful point! Everyone has come in contact with a creepily desperate person some time in their dating history. Best of luck!!

    In regards to laughing and making eye contact as being good relationship advice I have a great movie to recommend. It is a spoof on the horror hilljack genre (think Shawn of the Dead meets Texas Chainsaw Massacre). It is called Tucker and Dale vs. Evil and as you can guess the protagonists are the hillbillies. Dale is smitten with a pretty female co-ed and Tucker’s advice is to smile and laugh. Of course in this case it comes across creepy and a series of misunderstandings follow.

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    • Rachel October 19, 2011, 12:35 pm

      Just saw that movie this weekend! Genius!

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    • Ally October 19, 2011, 7:51 pm

      I loved that movie! Have been telling everyone they need to watch it 🙂

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  • Kerrycontrary October 19, 2011, 12:24 pm

    Wow what a great story!! I always think that dating advice is 98 percent crap because lets face it, meeting the right person is hard. It takes a lot of effort and even more luck. If you haven’t found that someone special yet I’ll be sending some positive thoughts your way. And they will think that you are trying just the right amount.

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  • Jan October 19, 2011, 12:27 pm

    Love this. I totally relate!

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  • Jan October 19, 2011, 12:28 pm

    Oh, and I forgot to mention that I’m sure this will score you some date offers.

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  • CG October 19, 2011, 12:30 pm

    If we still had the purple thumbs, I’m sure I’d get loads of them, but I have to say it: That pic is so ’90s, Scott totally looks like a member of Color Me Badd or an extra in the original 90210! 🙂

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    • Landygirl October 19, 2011, 1:22 pm

      Damn you! Now I’m going to be singing CMB songs in my head all day. Scott could probably use some eyebrow sculpting if he truly wants that look.

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      • CG October 19, 2011, 4:30 pm

        LOL I know, I have “I Wanna Sex You Up” going through my head too! And the guy next to him looks like he’s in Boyz 2 Men, so I’m alternating the Color Me Badd with some “Motownphilly.” 🙂

    • bethany October 19, 2011, 1:49 pm

      I’m assuming that since they were frat brothers 15 years ago that picture was taken in the mid-late 90’s… Those were the days! I can’t lie- I miss the 90s!!

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  • Christy October 19, 2011, 12:30 pm

    I’m gonna say it and I hate myself for it, but I want it to be said:

    I really don’t appreciate how you used a female pronoun to describe the fourth-grader who is bad at math. I understand that in an attempt at gender neutrality, you alternated between male and female pronouns. I applaud that. I would bet money you didn’t even do it on purpose. I just wish that at some point, it had been changed in an edit. Maybe think to yourself “This hints of stereotypes. I’m clearly not trying to offend anyone, and it’s just there for gender neutrality, but I’m going to change it anyway. [Even if I’m only changing it for the inevitable crazy commenter.]”

    Anyway, I hate to be that person. I just hate the idea (which I’m sure you don’t believe yourself, but it seems to be ingrained into our culture) that girls aren’t good at math or girls don’t like math. I try to remind people that even harmless phrasings like this one can discourage girls from doing math. (Because it’s something that we don’t even think about anymore. We don’t act like it’s an issue.)

    Anyway, I’m sorry to be “that person.” I think yours is a great article. I too hate it when people give me generic and unhelpful flirting advice. I think I’m going to give trying hard a shot. (Maybe it’s more successful when a lady uses it on another lady? Maybe? Let me have hope at least?)

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    • BecBoo84 October 19, 2011, 1:05 pm

      Seriously, I’m only about being gender neutral or whatever you want to say, but I think you’re trying to make a mountain out of a molehill.

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      • JK October 19, 2011, 1:49 pm

        Thank you. I thought the same thing.

        I blame it on english, there isn´t a gender-neutral way to talk about people.

      • Portia October 20, 2011, 10:48 am

        Guys, there is an option, it’s called singular gender neutral or “epicene” they. It’s valid in speech and it has been used throughout the history of English. I bet no one but a grammar maven would have noticed it anyway and then, no gender stereotypes!

      • spark October 19, 2011, 8:08 pm

        Definitely. It sounds like she is *trying too hard* to stir up some drama where there is none. It sounds like she wants to ride of the waves of the JCPenny girls-suck-at-math-tee controversy.

    • KAM October 19, 2011, 1:15 pm

      I doubt the author was trying to perpetuate stereotypes with his comment. It was probably more likely that he just wanted a boy/girl scenario.

      I’ll probably get a lot of flack for this but I think some people need to chill about making everything, everywhere so PC. I’m a woman and I hate math (and suck at it to boot) but I don’t worry about how my existence may or may not further pre-existing stereotypes. I don’t feel any less equal because I can’t do logarithms or integers. That’s the way I am. I just move on and focus on the things I do rock at.

      I think it’s a more serious issue when a woman feels like a stereotype holds any weight at all. It doesn’t. It’s all how you view yourself and how you allow people to treat you.

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      • JK October 19, 2011, 1:53 pm

        I´m with you on the 2nd paragraph. I don´t live in the US, where I live is decidedly less PC, but still I´m amazed sometimes by the lengths people go to, to not offend anyone.

      • LennyBee October 19, 2011, 5:19 pm

        Didn’t notice the gender pronoun, and don’t care now that it’s been pointed out, and kind of agree on not worrying so much about being PC constantly. BUT stereotypes do hold weight, even when we’d prefer they didn’t. Stereotype threat causes a lot of people to perform more poorly than they should (across a variety of stereotypes, not just girls + math), just because of knowing that the stereotype exists. It’s thought to be one of the causes of the racial and gender gaps in schools.

      • KAM October 19, 2011, 5:48 pm

        Oh, I definitely agree but I do think it’s, primarily, up to the individual to overcome the stereotype, whichever one it is. It doesn’t have weight if you don’t allow it to. Realizing that fact certainly takes long enough (took me about 20 years) and socio-economic factors definitely complicate the matter but it’s still as simple as deciding on who you want to be and how you want to be treated (though I can’t ignore the fact that it’s all easier said than done).

    • CMF October 19, 2011, 2:01 pm

      Oh God, really? Then I’ll chime in and say why did he have to make the dyslexic kid a boy? Because boys have a harder time with reading! Or are more likely to be dyslexic? How dare he point that out. I’m offended on behalf boys everywhere. Clearly, every child should be written as “The Child,” or simply “it.” Sheesh.

      Lighten up, people.

      Great story, Dennis! And you’re way hotter than Scott. Just saying.

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      • JK October 19, 2011, 2:09 pm

        Don´t forget the seagull!! It should be offended because Dennis perpetuated the stereotype that they crap everywhere!!! 😉

      • Dennis Hong October 19, 2011, 2:30 pm

        Awww, thanks!

        *makes hand into the shape of a gun, points and shoots, winks, smirks, makes hang loose sign next to right ear, silently mouths “call me,” winks again*

        Trying too hard?

    • Dennis Hong October 19, 2011, 1:31 pm

      The other option would’ve been a dyslexic girl and a boy who needs math help, in which case you probably would’ve bitched me out even more.

      I think you need to cut me some slack here.

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      • jane October 19, 2011, 1:55 pm

        Agree. I think you’re reading way too much into it. Great essay Dennis!

    • Eljay October 19, 2011, 3:26 pm

      Holy cow, from all the awesomeness in this article, this is what you come away with? Wow, just wow.

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    • Skyblossom October 19, 2011, 4:18 pm

      My son hated math and my daughter doesn’t like it either. My husband and I both liked it more. I don’t see any harm in saying she didn’t like math.

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    • Slamy October 19, 2011, 4:26 pm

      so it’s not ok for the hypothetical girl to be bad at math, but it is ok for the hypothetical boy to be dyslexic?


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      • Slamy October 19, 2011, 4:28 pm

        nevermind. didn’t read all of the comments. but still.

    • katie October 19, 2011, 11:09 pm

      im just gonna throw it out there that in my high school, the academics were dominated by females. and they were all amazing at math. i think we had 2 validictorians and like 4 salutitorians…. all girls.

      go justify your stereotypes somewhere else.

      oh, and its less offensive that the boy is dyslexic? because THAT doesnt reek of the whole boys suck at learning and just want to crush each other in football….

      people are so stupid….

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  • Sarah October 19, 2011, 12:39 pm

    Great story! Yeah, I knew the creepy desperate dude who always struck out with the ladies. Once he actually got a first date with a girl but when she canceled because she was sick (or “sick”) he showed up on her front door with roses and a teddy bear that said “I Love You” on its belly. Swing and a miss. I knew he was a sweet guy and a great catch, but he just didn’t know how to give that impression out to anyone but his friends.

    I know you’re probably not looking for ideas or anything, but you mentioned you talk to groups of other people when you’re out. If you go around to too many groups to chat with women, that actually might be the problem. I used to love talking and flirting with a guy at a bar or something, but if it was obvious he was talking to a bunch of other girls in the bar, it would give off the impression to me that he was just checking out his best options (I know that’s not true, but its been a buzzkill for me every time that I would notice that happen).

    The best ways I’ve been hit on in a bar is if I notice a guy looking at me from a distance. Then, we’ll stare at each other for a second, and then he’ll look down, just to look back up and smile at me a little. if I’m not into him I’ll purposely know to look away, but if I’m into him I’ll keep looking back. Then he’ll come over and ask to buy me a drink. That way its not overly done and the girl still gets to feel special.

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    • artsygirl October 19, 2011, 1:56 pm

      I always suggest volunteer work to my guy friends who have not had tons of luck with girls. The best is the Humane Shelter because they always need guys to help out (90% of their volunteers are young women). You will statistically in an advantageous situation and you get to help out animals so pros all around.

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    • Skyblossom October 19, 2011, 4:21 pm

      And when a person is standing or sitting their belly button will be pointing at whatever has their interest, say a girl, a car or a keg of beer.

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  • Landygirl October 19, 2011, 1:20 pm

    Am I the only one who thinks the bird crap/bleach pen incident is creepy? Who would do that other than a stalker chick?

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    • bagge72 October 19, 2011, 1:31 pm

      If your on vacation in a different state it isn’t creepy it is a hot one night stand!

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      • bagge72 October 19, 2011, 1:41 pm


    • KBobK October 19, 2011, 1:33 pm

      It’s absolutely creepy! Creepy desperate. She didn’t let him answer, and I for one would be pissed if someone decided to bleach my shirt trying to “be nice.”

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    • Rachel October 19, 2011, 1:36 pm

      Seriously. And it sounds like she left the bar to go BUY the bleach pen!

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      • Rabbit October 19, 2011, 2:47 pm

        I assumed she had it in her car.

    • Sarah October 19, 2011, 1:49 pm

      Cut to the girl paying the seagull in the parking lot….

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      • haggith October 19, 2011, 2:36 pm

        hahahaha… i can definitely picture that!!!

    • Dennis Hong October 19, 2011, 2:05 pm

      Yes, after we were finished snickering at Scott, as he sat there in bewilderment while a strange woman cleaned off his shirt, we did think the woman was a little… odd.

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  • AKchic October 19, 2011, 1:58 pm

    Some guys just exude charisma. They don’t mean to. Just like some women do. Call it a curse, a gift, whatever.

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  • Shadowflash1522 October 19, 2011, 1:58 pm

    I have to agree. “You’re trying too hard!” screams of condescension; you might as well come out and say “you’re doing it wrong,” which is just as vague and unhelpful. However, pointing out that your grimacing rictus of a smile makes you look like a creepy circus clown — yes, that falls into the category of “trying too hard”, in the sense that you’re trying so hard you might actually pull a muscle. But I would rather be told exactly what I’m doing wrong, even if it’s that blunt.

    I think that “trying too hard” is a legitimate statement when (creepy-desperate code language aside) it means that your stress is showing. In other words, if you stress too much about appearing relaxed, you telegraph ‘stressed’ instead of ‘chill’ to your prospective mates.

    My roommate in college worried a lot sophomore year about the fact that she hadn’t had a boyfriend yet and was two years into “the college experience”. I, on the other hand, had had two boyfriends and have never once cared (much less worried) about my dating timeline. We’re both very similar people in looks and temperament, so the only advice I could offer her really was, “relax!” She’s mellowed out considerably in the past couple years, and sure enough there are a few boys sniffing around her now. There’s probably more to it than that — she’s gained a lot of confidence and lost a little weight too — but I think it does a lot for your “I’m not a creepy, desperate wo/man” image if you actually *aren’t* feeling desperate.

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  • Painted_lady October 19, 2011, 2:32 pm

    I don’t know if this will be helpful at all, but one of the things that has always turned me off about men who seem to be working really hard right after first meeting me is something like this. He doesn’t know me that well, and he’s working this hard, which makes me think that he would try that on anyone, which means that I’m just filling a spot for him, and I’m a person, not a placeholder. So yes, absolutely go out of your way to be appealing, but be aware that there’s a line you cross between, “Hey, you’re really interesting” and “OH MY GOD LET’S GET MAAAAAAARRIEEEEEEED.” I wish I could pinpoint it, but it varies from woman to woman, of course.

    The other thing is, like you were saying, level of appropriateness. You can only convince a woman to continue to like you or to stop liking you. You can’t convince her to be attracted to you when she’s not interested at all. Painted_dude used to be far less smooth than he is now (which, trust me, was pretty scary), and I finally told him – not just after he tried to ask me out, but after he’d been shot down by like six girls in a row who all pegged him as trying too hard – that if he was going to take every kindness, every smile, every not-completely-bitchy thing a woman did as a sign she was interested, all he was convincing these women of was that to make him get the hint they were going to have to be total bitches to him.

    I’m not saying you’re doing any of this, and even if you are, my advice may not be helpful. Ultimately, dating kind of sucks, and I’ve never been very good at meeting people either.

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  • Jenny October 19, 2011, 2:43 pm

    Nice article, Dennis. I think it’s a good idea to go around and talk to people when you’re out…but at the same time, don’t talk to TOO many girls. I remember when I was in HS, there was this nerdy kid who seriously asked out every single girl in my grade. Needless to say, I wasn’t too flattered when it was my turn. If a girl notices that you’re going around and talking to a bunch of girls, its going to be a huge turn off for her. There was a study done that found the least attractive quality a person can have is “willingness to settle when choosing a mate”. If a girl at a bar thinks you’d go home with ANYBODY, it won’t be attractive to her…and if it is, that’s not a girl you’d want to go home with anyway 🙂 Now, I’m sure you’re not at a bar wandering around from group of girls to group of girls…but I thought it was a point worth making, anyway.

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    • Dennis Hong October 19, 2011, 3:17 pm

      No, I just pick one group and follow them around the rest of the night…. 😉

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  • melanie October 19, 2011, 3:02 pm

    I actually had a date with a guy a few weeks ago. On paper, he was perfect. Even toward the beginning of the date he was charming and witty; I felt like there could have been a connection. Then, I got this weird feeling about him as the date went on. He was just trying too hard.

    I was curious why I had a stand offish feeling toward him, so I started reading some articles on psychology. I read that my inution was telling me to get away from this guy. Because, someone that “tries too hard” sets off a ‘danger’ signal so that you can protect yourself. One of those things that has stuck around through evolution, I suppose. Thought it was interesting.

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  • FireStar October 19, 2011, 3:09 pm

    Agreed – big difference between trying and trying too hard.

    For me a guy could look like Henry Simmons – but if he didn’t make an effort to be engaging then he could sit at the bar by himself. If someone needs to remember your name beyond 24 hours then your personality definitely has to be in play.

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  • Budj October 19, 2011, 3:29 pm

    Dennis – I’d do you.

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    • FireStar October 19, 2011, 3:47 pm


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      • Dennis Hong October 19, 2011, 7:14 pm

        Hey now, if there’s one thing I learned, it’s that if someone offers to do you, you should never laugh. :-p

  • Elaina October 19, 2011, 3:20 pm

    Great article. I totally agree that unsolicited dating advice is incredible frustrating. I end up on the opposite end of the spectrum — the advice I get is all about how I don’t try hard enough. But I agree that it does take effort to put yourself out there and I applaud you for embracing that.

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  • moonflowers October 19, 2011, 5:22 pm

    Maybe it’s the busybody in me, but a lot of times when I get hit on or asked out and it goes south rapidly, I really want to tell the guy specifically what he’s doing wrong. It might be the field I’m in (engineering), but I meet so many men who are clueless and then end up cursing the universe or something for being FOREVER ALONE, when all they really need to do is hone their approach skills.

    “Trying too hard” is rather unhelpful, but sometimes it’s hard to explain it. Like when I go on a first date and the guy is hanging on my every word, even though I’m just talking about a boring night in at home – not only do I not expect that sort of attention, it’s a major turn off because it telegraphs “I am being super attentive and on my best unnatural behavior for the sole purpose of pleasing you as much as possible.” I can see why a guy might think it’s a good thing to do, but it betrays a lack of confidence in one’s own natural appeal, minus exaggerated attention, and it also comes off as desperate. He barely knows me, why should my judgement of him mean so much to him yet?

    There’s an idea in psychology that the person who betrays a greater need for someone else in a relationship is handing over the power in that relationship. On the other hand, if a guy can truly come off as, “Hey, you’re cool, but I’m cool too with or without you,” and can casually walk off after making his interest clear (not wishy washy!), that’s incredibly hot. Not making a big deal whether a girl likes him immediately or not says a lot about his confidence in himself, and that he feels totally comfortable being on his own, which makes him cool. And nothing feels cooler to a chick than being shown some attention by a cool guy. 🙂

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  • TheOtherMe October 19, 2011, 10:13 pm

    Well Dennis, As I had commented ( a few times ) on the original article, I can only repeat : well done !

    -T.O.M.- —> for old time sake 😉

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  • Dennis Hong October 19, 2011, 10:49 pm

    Hey everyone, thanks for the kind words! I’m glad you liked this essay.

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    • Budjer October 20, 2011, 10:49 am

      Yea dude. Really interesting / different from the normal. I liked it a lot…and I think we all have a friend like Scott so I feel ya.

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      • Budjer October 20, 2011, 10:50 am

        and holy exactly 12 hours.

  • Lydia October 20, 2011, 6:23 am

    Great essay! I can totally relate. I did online dating for a while and a lot of people would tell me that I was “looking too hard” and that “love should just come naturally”. Some even say that love only comes when you AREN’T looking for it. I always thought that was bullshit and would reply “well, I can just stay at home and read my book and hope for Prince Charming to one day spontaneously ring my doorbell, but I don’t think that’s going to happen, so I will keep actively looking”. And it worked too – I’m now engaged to a guy I met on OkCupid. 🙂

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  • 6napkinburger October 20, 2011, 11:52 am

    For me, my sadness about this phenomenon goes beyond the “well-intentioned” but useless advice. It goes to the root of it. It makes me so profoundly sad that, as humans, “reward” people for the crime of wanting something by denying it to them.

    Think of the sad, lonely girl in middle school, the socially awkward one. All she wants is friends. So she tries so hard to get people to like her, to make friends. But her desperation is why no one will be friends with her. The other kids avoid her for the EXACT reason that she wants them not to.

    We are told in life to go for what we want, in careers, in school. But in anything to do with social situations, its the worst sin. “Trying too hard” is not just a turnoff in the dating world, its the kiss of death for anything. You want people to like you? You’re a tool, a kiss-ass, a loser. The most popular people act like they don’t care. The guy who acts like he doesn’t care doesn’t get promoted (or not usually). The person who blows off projects doesn’t get a corner office, but the person who blows off plans is homecoming king.

    The part that makes me cry is when it comes to people who cannot help it; who can’t read social cues or understand when they aren’t acting aloof enough. They get lonely too and they understand rejection; they just don’t understand WHY they are being rejected. It breaks my heart. I understand when its “strangers” and if there’s some sort of stranger-danger-creepy factor. But when it isn’t strangers, when there’s no danger, the idea that we reject people because they like us and want us to like them back, in the friend context, I don’t know. It makes me hate humanity.

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  • delilahgem October 21, 2011, 4:54 pm

    Dennis, all late and wrong, but I read this the other night and didn’t get a chance to comment. I loved this! Great job 🙂

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  • theOtherDude May 2, 2014, 6:53 pm

    Wow, pretty useless article.

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