History Main / AwkwardKiss

* Borderline on ''Series/{{CSINY}}''. 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...I mean, I didn't mind doing that...Lemme just get our coats...

-->-- '''Lorraine Baines''', ''Film/BackToTheFuture1''

* ''Fanfic/AdviceAndTrust'': 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... [[TheBigDamnKiss and things changed]]. ''[[ForWantOfANail A lot]]''.

* At first Miwa and Saeko's first kiss in ''Manga/HowDoWeRelationship'' seems pretty good, but it turns out Miwa has reservations about kissing in the clubroom, causing it to turn sour. Then Saeko asks if that was Miwa's ''first kiss'' overall, and Miwa instead tries to change the subject by throwing herself back into kissing-- almost literally, causing the two to end up banging their teeth together. Then Miwa tries taking the lead, which Saeko notes she's notably bad at. ''And then'' [[spoiler: Mikkun ends up walking in on them.]] To top it all off, in a bonus comic Miwa reveals that Saeko ate a sandwich before this moment, making the kiss taste like mayonnaise.

* ''Fanfic/TheOneILoveIs'': In episode 4, Asuka dares Shinji to kiss her during their date. Tired of her taunting, Shinji grabs her shoulders and kisses her forcefully. Although they enjoyed it for a bit, their kiss was more awkward than romantic.

[[folder:Film]]

* ''Film/JumanjiWelcomeToTheJungle'' has Spence and Martha try a kiss while playing the titular game. Both being absolutely inexperienced at kissing, they end up with some weird head-waggle and not properly touching their lips together. A later kiss, near the end of the movie, ends up working out much better.

* In the first ''Film/BackToTheFuture1'' movie, Marty's [[{{Squick}} 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."
* ''Film/MinuteMen'': 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 ''Film/TheProposal'', 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 ''WesternAnimation/CloudyWithAChanceOfMeatballs'', Flint's first kiss with Sam, due to him not getting the hang of puckering his lips.

* In ''WesternAnimation/PenguinsOfMadagascar'', 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 [[OverlyLongGag a good half-minute]].
-->'''Skipper:''' You mess with the bull you get the horns, Private.
* ''Film/PlanB'': When Bruno and Pablo first kiss to play up their GayBravado in front of their [[GuyOnGuyIsHot interested]] friend Ana, the kiss is so brief and stilted that Ana later calls them out on how lame their attempt at GayBravado was and insists they kiss a second time to make up for it, which goes only slightly less awkwardly than their first attempt. They also kiss a third time, this one done allegedly to help Bruno [[PracticeKiss practice]] for an acting role, which actually goes pretty well until they pull away and stand in awkward silence for a long time, the awkwardness this time being less "we're two straight men who find this weird" and more "we're starting to realize that we actually really enjoy kissing each other, but don't want to admit it because we're ''supposed'' to be straight".
* Played with in ''Film/SpidermanFarFromHome'' between Peter and MJ. After confessing their feelings for each other, their FirstKiss an {{Adorkable}} one; hesitant and shy, with body language making it clear that neither of them know what they're doing, and both really hoping they're reading the other person correctly, ending with little more than a peck. It is followed a few seconds later with a much longer, more confident and enjoyable kiss.

* ''Series/{{Firefly}}'' comes close to one of these in "War Stories", when PlatonicLifePartners Mal and Zoe are about to kiss after Wash's repeated jealousy. Wash interrupts, the point being made.
* Wesley and Cordelia on ''Series/BuffyTheVampireSlayer'' kiss after some time spent with {{UST}}. It quickly becomes this, and both find new love interests when they cross over to ''Series/{{Angel}}'' and remain BetterAsFriends- amusingly, enough so that they're able to joke about their disastrous kiss for years to come.

* The titular heroine of ''Series/UglyBetty'' has a slightly sad one of these with Marc, who kisses her in an attempt to hide his sexuality from his homophobic mother.
* In ''Series/HowIMetYourMother'', 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 ''Series/HouseOfAnubis'' 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 [[BelligerentSexualTension insult him]] like Patricia does, and Piper didn't even know what was going on.
* ''Series/{{Friends}}''
** Chandler keeps giving awkward kisses to both Phoebe and Rachel in order to cover his {{Secret Relationship}} with Monica whenever the gang sees them kissing.
** "The One Where Everybody 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.
* Inverted in ep 7 of ''Series/EyeCandy''. 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 ''Series/{{CSINY}}''. 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...I mean, I didn't mind doing that...Lemme just get our coats...

* PlayedForLaughs during Creator/NeilPatrickHarris's turn as Westley in ''Series/HomeMovieThePrincessBride'', for the scene where Westley and Buttercup reunite after rolling down the hill and share a kiss for the first time. Harris's real-life husband [[GenderFlip David Burtka plays Buttercup wearing a cheap wig and a dress]], and after Buttercup's heartfelt confession that she'll never doubt the power of true love again, Harris's Westley proceeds to slobber all over Burtka's face.

* After several seasons of denying Zaboo's advances on WebVideo/TheGuild, Codex experiences an UnrequitedLoveSwitcheroo. 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 BetterAsFriends.

-->-- '''Lorraine Baines''', ''Film/BackToTheFuture''

* In the first ''Film/BackToTheFuture'' movie, Marty's [[{{Squick}} 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."

[[quoteright:350:[[Film/JumanjiWelcomeToTheJungle https://static.tvtropes.org/pmwiki/pub/images/awkward_kiss.jpg]]]]

* ''Film/ThePrincessDiaries'':
** 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 RomanticFalseLead. She gets her epic kiss once she realizes the right guy is her [[ChildhoodFriendRomance 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 BetterAsFriends.

* At first Miwa and Saeko's first kiss in ''Manga/HowDoWeRelationship'' seems pretty good, but it turns out Miwa has reservations about kissing in the clubroom, causing it to turn sour. Then after Saeko asks if that was Miwa's ''first kiss'' overall, she instead tries to change the subject by throwing herself back into kissing-- almost literally, as the two end up banging their teeth together. Then Miwa tries taking the lead, which Saeko notes she's notably bad at. ''And then'' [[spoiler: Mikkun ends up walking in on them.]] To top it all off, in a bonus comic Miwa reveals that Saeko ate a sandwich before this moment, making the kiss taste like mayonnaise.

* ''Anime/NeonGenesisEvangelion'': 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 him 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.

* ''Fanfic/TheOneILoveIs'': 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 ''Film/MeanGirls'' 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 ''Film/ThePrincessDiaries'' 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 RomanticFalseLead. She gets her epic kiss once she realizes the right guy is her [[ChildhoodFriendRomance old friend]].

* ''Film/JumanjiWelcomeToTheJungle'' has Spence and Martha try a kiss while playing the titular game. Both being absolutely inexperienced at kissing end up with some weird head-waggle and not properly touching their lips together. A later kiss, near the end of the movie, ends up working out much better.

* ''Series/{{Friends}}'':

* ''Series/{{Community}}'':

* ''Series/SchittsCreek'':

* The ''Series/{{Friends}}'' episode "The One Where Everybody 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.

* In ''ComicBook/ScottPilgrim'', Scott, after his breakup with Ramona, tries kissing his ex-girlfriend Knives. The ensuing kiss is so awkward that the narration states that it made everyone feel terrible, "including even [[BreakingTheFourthWall you]]".

''Webcomic/TheShufflers'': Märchen and Hiddenite get their lips literally stuck together thanks to Dutchkiss’s (accidental) magic.

-->'''Christine''': I didn't mean to do that...*Did* I mean to do that?

* In ''WesternAnimation/CentralPark'', Season 1 "[[Recap/CentralParkS1E8HotOven Hot Oven]]", when Brendan goes to kiss Molly, he misses her lips and accidentally kisses eye because he got distracted when he saw Owen and Paige peeking out the window. When Molly tries to kiss Cole, she misses his lips and kisses his eye. They try kissing one last time but they hit each other's teeth.

* ''WesternAnimation/BobsBurgers'': In "The Land Ship", Tina's new crush Jordan turns out to be a ''terrible'' kisser. His every attempt to kiss Tina just involves awkwardly shoving his whole mouth onto Tina's face like he's trying to swallow her whole.