Bob meets Alice. Alice gives Bob attention. Bob attempts to get Alice's attention the wrong way. Hilarity Ensues.
This trope occurs when the boy, having gotten the girl's attention passively — i.e. through quirky, unconventional, non-stereotyped aspects of his personality — then attempts to get her attention through a more "stereotyped" manner, a la Extraverted Nerd or Dogged Nice Guy. This either turns the girl off, or confuses her, or she misinterprets it.
- In Ah! My Goddess, Keiichi's attempts to work up the courage to kiss Belldandy cause him to heat up. Belldandy misinterprets this as a fever and tries to "cure" him with her magic.
- When Minoru from Gokusen started dating a girl, Kumiko fired him so that he could have a normal, respectable life with his girlfriend... who immediately dumped him. She only liked him because he was yakuza.
- In an episode of Full Metal Panic? Fumoffu, Jindai High School's social science club decides to hold a flirting contest in order to decide which school club will get to use the new classroom that has opened up. Shinji convinces Sousuke to join the photography club's team, assuming that having a handsome Chick Magnet on their side would guarantee them a win. Unfortunately, Sousuke is specifically a Clueless Chick Magnet who unwittingly wins people over through endearing social awkwardness and who has absolutely zero experience with romance, courtship, or just plain people-ing. Even after Kaname gets him to understand that a "girl hunt" does not allow for literally capturing the girls in question, Sousuke winds up immediately scaring off every single woman he approaches (save for an old lady who leads him forget the contest entirely in order to help her pick out a present for her grandson), resulting in an embarrassing loss for the photography club.
- Disney's Aladdin: Al has already charmed Jasmine by being himself, but his "Prince Ali" persona just comes off as another Royal Brat like the ones she rejected as suitors. (Although note that the disguise and fake name themselves are pretty much necessary—the Sultan isn't going to let Jasmine marry a commoner.)
- Far and Away: Due to Shannon's wealthy upbringing, Joseph feels inferior. So, he tries to become somebody he thinks she would find attractive, somebody rich and classy. This only makes her annoyed with him, because she liked how different he was from the people she knew growing up.
Joseph: I tried to prove myself to you, but I know nothing of books or alphabets or sun or moon or... All I know is Joseph loves Shannon. That's all that really matters to me.
- In The Wedding Singer Robbie manages to win Julia's heart by just being himself, but then he becomes convinced that she'd be more interested in him if he were rich so he starts trying to land a high-paying job. He also begins to slide into Jerkass territory and drives Julia away before winning her back by just being himself.
- In Groundhog Day, when Phil has his first day where he was doing great with Rita, he wants it to continue. When he tries to force the same reaction during the next loop, his forwardness actually pushes her away. He finally gets it right.
- One episode of M*A*S*H features Radar catching a girl's attention through just being sweet and Radar-like, and without realizing it, and tries to grab her attention again by pretending to be an ex-footballer, through ignoring her and 'playing cool', and then by trying to be 'interesting' with talk about rabbits. She's mostly confused, but in the end he admits what he's been trying to do and they end up together... until the next episode.
- In an episode of iCarly, Sam tries to attract a boyfriend by being girlier. Turns out he likes her the way she was.
- In one episode of The Office, Michael unaware he's being romantically set up is quirkily joking his way into the heart of Pam and Jim's friend. When Michael learns the truth, he exits the bar, unbuttons the top button of his shirt, puts on a backwards hat, and re-enters as "Date Mike," whose antics are so obnoxious the girl leaves early.
- An episode of Family Ties had a guy getting ready for a date with Mallory by asking Alex for tips. Alex (who apparently was genuinely trying to help) proceeds to give a bunch of chauvinistic advice (starting with ordering for her and getting worse from there). Naturally, it doesn't end well.
- Alex's advice might have worked well for the kind of woman Alex would be interested in dating. For his sister, who is more or less the political opposite of the kind of woman he'd be interested in dating ... not so much.
- The narrator of Olivia Holt's "Had Me @ Hello" just wants to dance with her Love Interest, but he doesn't realize that.
You don't have to try too hard
You already have my heart
You don't got a thing to prove
I'm already into you
- In Gunnerkrigg Court, Kat tries to give herself a makeover to attract the attentions of Alistair. Annie subsequently removes the makeup and tells her she looks fine the way she is.
- Parodied in an early mini-arc of Least I Could Do: Rayne spends half an evening trying to charm an interested girl at a bar by using his various tricks and zany techniques. When she finally gets mad and calls him on it, he admits that he had been messing around, and resolves to just be his true self... the whole time slipping into a completely artificial Dogged Nice Guy persona. Mick is unhappy, to say the least.
- In the episode "The Fortune Teller" of Avatar: The Last Airbender, Sokka gives advice to Aang on how to get a girl to like you (of course, Aang wants to impress Katara, but Sokka thinks he's talking about Meng). His advice is that Aang's way too nice, and that he needs to act very aloof. Aang (unsuccessfully) attempts acting aloof, which both annoys and confuses Katara. Ironically because he doesn't care about Meng at all he does a GREAT job of acting aloof to her, impressing Sokka.
- The Legend of Korra Bolin had initially attracted Opal without even realizing it and needs a genius of love like Mako to both spell it out and that his previous love interests were either ditzy (Ginger) or crazy (Eska), so it's about time to aim for someone whose neither of those things. Bolin initially tries to act smooth which only turns Opal off. She immediately calls him out on it then advises him to Be Yourself, which greatly improves both their growing relationship and each's Character Development fitting with the franchise's Central Theme of Balance.
- Chris on Family Guy once took girl advice from his dad with predictable results.
- Lieutenant Kiff from Futurama had already kicked it off with Amy, but he's too shy to follow it up. So Zapp Brannigan offers to give him romantic advice. Considering that Zapp's idea of a pick-up line is "I find that the most erotic part of a woman are their boobies", Kiff's next date doesn't go very well.
- Candace in Phineas and Ferb. Jeremy obviously likes her just as much as she likes him, but she's so blinded by her own insecurities that she still goes out of her way to make him notice her.
- Happened in My Little Pony Tales with the Twice Shy Lancer and Bright Eyes each getting Unnecessary Makeovers from their friends Ace and Melody. Acting 'cool' only causes them to lash out — "I didn't you were such a JERK!"/"And I always thought you were smart, not some AIRHEAD!" — but they reconcile after dumping their makeovers and just acting normally, much to the mystification of their friends.
- Nitz in Undergrads tries to woo Jessie (after accidentally seeing her naked) by making traditional grand romantic gestures at her, even though she liked him already and these gestures repelled her.
- Not to mention just assuming that they were already in a relationship the minute he found her attractive. "Please don't break up with me!"
- In the South Park episode "South Park is Gay", the men and boys of South Park adopt the "metrosexual" craze that is sweeping the country (i.e. they start acting effeminate and become obsessed with grooming and fashion). At first their wives and girlfriends like the way their men are more hygenic and willing to communicate, but after a while they start to grow tired of how self-absorbed and narcissistic the men are getting. At the end of the episode the men abandon metrosexuality, and their women admit that men need to be masculine even if that means they're sometimes gross.
- In the OK K.O.! Let's Be Heroes episode "Second First Date", it's revealed in a flashback that Enid used to have a crush on Rad in middle school. He was a lot less macho and narcissistic than he is today. However, he gets bad advice from his friends and acts like a jerk for most of their first date, ruining whatever chance at romance they could have had. Even after realizing he blew it and would have had a better shot if he had been himself, his friends convince him to deny any responsibility and "double down." Now Enid is extremely cynical but has a rather odd, platonic friendship with Rad.