Redundant Romance Attempt

Boy meets girl. Girl gives boy attention. Boy attempts to get girl'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.

Nearly always leads to An Aesop. Say it with me: "You should have just been yourself all along!"

Anime & Manga

 * 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.

Film
"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."
 * Disney's Aladdin: Al has already charmed Jasmine by being himself, but as Prince Ali he just comes off as another spoiled royal brat like the ones she rejected as suitors.
 * 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.

Live Action TV

 * One episode of MASH features Radar catching a girl's attention through just being sweet and Radar-like, and without realising 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.

Western Animation

 * 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.
 * 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.

Webcomics

 * In Gunnerkrigg Court on this page, Kat tries a makeover on herself cause there's a boy she likes. Her best friend Annie fixes this by wiping off the horrifying clown makeup and on the following page telling Kat that makeup ain't gonna make her look prettier to a boy who Already Totally digs her. :)