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- Neon Genesis Evangelion: In episode 15, Asuka and Shinji kiss, but due to their personal traumas it goes awfully wrong. Asuka wanted to kiss Shinji but she did not want to look interested, in case that he rejected her, so she told she wanted to kiss him because she was bored. Shinji wanted to kiss her but he did not believe she was interested in him, so he initially resisted. They went forward with the kiss but Asuka held Shinji's nose the whole time to pretend it was not a big deal in case he turned her down. And precisely because she was pretending it was not a big deal, Shinji did not dare to do anything, and he remained motionless and unresponsive. And precisely because he remained motionless, Asuka thought that he was turning her down, so after breaking the kiss, she immediately ran to the bathroom with the excuse she wanted to rinse her mouth of the taste, when she in fact was trying to hide how deeply hurt she was by this perceived rejection. To Shinji the whole mess ended up as another blow to his self-esteem and for Asuka it was one of her first steps towards her mental breakdown later in the series.
- Advice and Trust: Subverted. In the first chapter, Asuka and Shinji's kiss was very awkward and tentative at the beginning and was heading towards this path when Shinji accidentally placed his hands on her waist to steady himself... and things changed. A lot.
- From an anecdote from Father Brainstorm in Calvin and Hobbes: The Series:
"....Then she moved in to kiss him and as he saw her puckering up and moving forward, he smiled and she accidentally kissed him on the teeth!"
- The One I Love Is: In episode 4, Asuka dares Shinji to kiss her during their date. Tired of her taunting, Shinji grabbed her shoulders and kissed her forcefully. Although they enjoyed it for a bit, their kiss was more awkward than romantic.
- In the eleventh chapter of Neon Genesis Evangelion: Genocide, when Shinji and Asuka share a kiss properly, Shinji remembers how awkward and strange was their first kiss.
It was not their first kiss, but it was the first time it felt right. Before Asuka had teased and goaded him into kissing her, even bringing up his dead mother. Then she had held his nose and pinched it until he turned blue while kissing him. It had not been entirely unpleasant, just strange. Now it was different.
- In 27 Dresses, Jane spends most of the movie with a crush on her boss. But when they finally do kiss...nope, no fireworks.
- In Mean Girls Janis and Damien have what would be an epic movie ending kiss in any other movie... Except here Damien is gay and Janis is a straight girl everyone thinks is a lesbian. The kiss ends up being a peck and the consensus from the two is "Ew. No."
- In The Princess Diaries Mia wants her first kiss to be an epic moment where her foot pops up like in old movies. Unfortunately, her foot gets stuck in fishing net on the floor of the shack they were hiding in, and she was with a Romantic False Lead. She gets her epic kiss once she realizes the right guy is her old friend.
- The sequel has one as well, when Mia and Andrew try to kiss to see if they have any romantic chemistry at all. Cue extremely uncomfortable liplock and the realization that they are definitely Better as Friends.
- Happens between Shaggy and Velma at the end of Scooby-Doo! Curse of the Lake Monster, in a Better as Friends example.
- In the first Back to the Future movie, Marty's teenage mother pounces on him and kisses him passionately, much to his horror. She pulls back almost immediately, commenting that it was "like kissing my brother."
- Minute Men: Charlie's kiss with Jeanette is pretty awkward considering he had forgotten that the events leading up to their first kiss didn't happen yet.
- In The Proposal, Andrew and Margaret have one of these when his family insists on seeing a kiss. It quickly moves out of the "awkward" territory, to both parties' consternation.
- In Cloudy with a Chance of Meatballs, Flint's first kiss with Sam, due to him not getting the hang of puckering his lips.
- In The Wizard, Corey gets Kiss Dissed by Haley after she says she'd never kiss a guy. Corey responds with "A girl, maybe?" She responds with an awkward "Take That!" Kiss.
- In Penguins of Madagascar, after Private is told his birthday surprise, he's overcome with joy and gives both Skipper and Kowalski familial cheek pecks before moving on to Rico... who pulls Private back in and traps him in a big wet-sounding smooch for a good half-minute.
Skipper: You mess with the bull you get the horns, Private.
- Zigzagged in Batman & Robin between Robin and Poison Ivy. Robin quickly falls in love with Ivy and she spends a majority of the film seducing him. However, she isn't actually in love with him and is simply trying to kill him with her kiss. Eventually, once the two are alone in her lair she finally succeeds in sharing a passionate kiss with him, only to ruin the moment by revealing her true colors and taunting him. Robin then reveals he was wearing rubber lips to protect himself from her poison, having finally seen through her seductions. Ivy is visibly shocked upon realizing that she just revealed her love to Robin was false and revealed her plans to him for nothing, before glaring at him for stealing a kiss from her.
- Clary Fray has one of these with Sebastian Verlac in City of Glass, saying it felt just "wrong". Turns out that's because he's her real (demonic) brother.
- In Half Wild, Nathan quite passionately kisses Gabriel before Annalise comes back. Gabriel doesn't speak to him for a while afterwards.
- Humorously, this seems to be the default mode for Harry Potter's Lavender and Ron, due to a comic combination of hormones, overeagerness, and a lack of genuine chemistry.
- Firefly comes close to one of these in "War Stories", when Platonic Life-Partners Mal and Zoe are about to kiss after Wash's repeated jealousy. Wash interrupts, the point being made.
- Wesley and Cordelia on Buffy the Vampire Slayer kiss after some time spent with UST. It quickly becomes this, and both find new love interests when they cross over to Angel and remain Better as Friends- amusingly, enough so that they're able to joke about their disastrous kiss for years to come.
- On The Big Bang Theory Sheldon and Amy's kissing experiment goes well enough considering Sheldon was involved, but Amy was drunk and ends up throwing up right after. Unlike most examples, the kiss wasn't indicative of the couple not being well matched, it was just really bad timing on Amy's part.
- The titular heroine of Ugly Betty has a slightly sad one of these with Marc, who kisses her in an attempt to hide his sexuality from his homophobic mother.
- In How I Met Your Mother, every Halloween Ted looks for a girl he met on Halloween 2001 who dressed as a "Slutty Pumpkin." In 2011, he finally meets her, and after ten years of buildup, the lack of chemistry is amazing.
- The kiss between Eddie and Piper in House of Anubis sure is awkward, as Eddie thought Piper was her twin sister and his girlfriend, Patricia, and Piper had no clue who Eddie was. The kiss appeared to be rather strange for both of them, as Eddie expected Piper to insult him like Patricia does, and Piper didn't even know what was going on.
- The Friends episode "The One Where Everyobody Finds Out" has Chandler and Phoebe uncomfortably attempting to seduce each other which ends in a very awkward kiss. Hilariously, this was enough to make Chandler concede defeat.
- An episode before that has Chandler giving awkward kisses to both Phoebe and Rachel in order to cover his Secret Relationship with Monica whenever the gang sees them kissing.
- Inverted in ep 7 of Eye Candy. Lindy and Tommy are posing as a couple who've unknowingly rented an apartment being used for a voyeur website. They're so stiff and uncomfortable it's hilarious - until the voyeur cameras come online, and they need to make their act look more convincing. Tommy and Lindy's subsequent kisses are actually the only part of the entire undercover act that doesn't look awkward as hell; in fact, it looks absolutely real (Lindy's sort-of boyfriend, who's also watching the feed, certainly seems to think so). Probably because of the very UST (and other issues) that make Lindy and Tommy so uncomfortable acting like a couple in the first case!
- Borderline on CSI: NY. Mac and Christine are at a party with Christine's family and since everyone is talking about them, they decide to give them something to talk about. It's a bit romantic, but awkward too because it's so early in the relationship. Things do work out for them, though.
Christine: I didn't mean to do that...*Did* I mean to do that?
- Community - Britta befriends Paige, thinking she's a lesbian, who befriends Britta for the same reason. They show off their openmindedness by going to the Valentine's dance together, then up the ante by publicly, awkwardly kissing.
Britta: I've never done this before.Paige: Neither have I.Both: Wait, what?!?
- In Ménage à 3, Zii and Gary's first kiss, late in the comic's run, is supposed to be businesslike, but is rendered awkward by the fact that they are attracted to each other, but Zii doesn't want to admit it and and Gary is a Nice Guy and respects the fact that she doesn't appear to be attracted to him. This is a twist given that most of the cast are far more casual about far more than kissing.
- In The Monster Under the Bed, Shadow and Tim's first kiss gets derailed when preteens run into the realities of a pretty deep kiss.
Shadow: Eww! I think I touched your tongue with my tongue! Gross!
Tim: Yuck! I got your spit in my mouth!
- After several seasons of denying Zaboo's advances on The Guild, Codex experiences an Unrequited Love Switcheroo. The two decide they are incompatible, but their guildies throw them in the bathroom to kiss just to make sure. It was "like cardboard." The two decide they are Better as Friends.
Zaboo: [several seconds after deciding to be just friends] Hey, remember that time we got thrown into the bathroom and we started making out and it was, like, hardcore? ...Too soon?
- In the Regular Show episode "Bad Kiss", Mordecai and Margaret's first kiss is cut short due to Mordecai's bad breath.
- The Legend of Korra:
- In episode "The Sting" Asami kisses Mako out of desperation after finding out Future Industries is more or less ruined long after their breakup. Mako reacts with shock and quickly tries to change the subject back to the matter at hand.
- In "Night of A Thousand Stars'' this happens between Mako and Korra. Korra had forgotten about their recent breakup due to amnesia, and the former didn't have have the heart to explain it to her.