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Embarrassing Voicemail

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Oh no! You just left the most embarrassing voicemail ever! But it's not that big a deal, right?
The voicemail is usually left by someone to a person they feel easily humiliated around (a love interest, a boss, or a parent). Maybe they accidentally made a Pocket Dial while revealing a secret. Either way, the person who receives the voicemail is usually away from home (or their mobile phone if you can believe it) and won't hear it until they get back to the machine. So, rather than admitting their true feelings or owning their embarrassment, the person would rather get to the answering machine first and delete it. This could be by Wall Crawling an apartment complex, visiting the person's house to feign interest (and erase the message behind their back), or secretly fumbling around on the person's phone to delete it. This usually results in the message-recorder being caught, and Cringe Comedy ensues. In this respect, there's a lot of cross-over with Irrevocable Message.
Other uses of the trope is when someone leaves an embarrassing voicemail, but is so unaware that they make no effort to amend it. They could be the typical love fool who desperately asks someone out on the phone. In general, the person is so uncomfortable with sharing their feelings to the person that they'd rather do it over the phone and avoid the physical interactions.
In some cases, it's someone else's voicemail that causes the embarrassment. They could be about doctor's results, unpaid bills, or messages from your loved ones. In a house full of other people, it's understanding why someone might want to delete those before anyone else listens to it.
Although the trope has been modernised in recent years (now that everyone practically carries around their own answering machine of some kind), the height of its popularity was in the '90s and early 2000s when answering machines were being used the most. Lightweight, affordable, and uncomplicated answering machines with large capacities started really hitting the market in the '80s, but perhaps the resurgence of the studio Sitcom genre in the '90s (with shows such as Seinfeld, Friends and Frasier hitting screens) made the simple answering machine such an easy Stock Joke.
Compare with Irrevocable Message, What Did I Do Last Night?, Love Letter Lunacy.
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The Simpsons: In "Marge Be Not Proud", Bart is caught shoplifting. The store manager leaves a stern message on the Simpsons' answering machine warning them of Bart's behaviour. Bart races home to get to the machine before the rest of the family, and replaces the tape with the Allan Sherman single "Hello Muddah, Hello Fuddah."
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Parks and Recreation: In the episode "Kaboom", Leslie tries to find out why Andy is suing by calling him. He doesn't answer, so she leaves a very awkward voicemail.
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In Miraculous Ladybug, Alya tries to force Marinette to confess her feelings to Adrien on the phone. It goes to voicemail, and Marinette goes full Gibberish of Love, which is her norm for Adrien at this point. After leaving the message, she sarcastically asks what Alya expected her to say, referring to Adrien as "hot stuff" and straight out admitting her inability to form a sentence around him. Only then does the phone then indicate that it's stopped recording. Marinette, in full panic mode, steals Adrien's phone in order to delete the message (Adrien never does hear it).
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Jane the Virgin: In "Chapter Thirty-Nine" Jane recruits her ex-stepsisters to steal a professor's phone and delete an angry voicemail her mother had left on it.
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Community: In "Communication Studies", Britta leaves an embarrassing drunk dial message on Jeff's phone. Jeff tries to instill her confidence by getting drunk himself (in the hope of leaving her an equally embarrassing message). However, in his inebriated state, he calls Michelle instead. Jeff is terrified he offended Michelle and tries to avoid her, but the trope is subverted when it's revealed his voicemail was actually about how much he appreciated her.
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Peep Show: In one of Mark's early attempts to woo Sophie he leaves her the following voice mail while being egged on by Jez.
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Dilbert: In one early strip, Dogbert has the bright idea of waking Dilbert at 4AM to leave voicemail for his boss to create the impression that he's working around the clock. It goes horribly wrong when Dilbert groggily declares "I'm in my underwear and I thought of you". He tries to erase the message, but instead sends it to his entire workgroup.
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The Big Bang Theory: In Season 7, Sheldon gets drunk and leaves a voice message for Stephen Hawking about his feelings of inadequacy in the field.
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The Kenan & Kel episode "Dial O for Oops" revolves around the titular duo repeating all the insulting things Kenan's father said about his boss, only to realize everything they just said was recorded onto said boss's answering machine (Kenan had been trying to call the boss's daughter to ask her out on a date, only to get a voicemail). Hilarity ensues when the pair try to sneak into the boss's house to erase the tape before it gets heard and Kenan's father potentially loses his job.
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Swingers: Mike calls back a girl he just met in a bar. He continuously fumbles on his words and has to keep re-dialing to leave new messages. While leaving the sixth message, she finally picks up.
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Seinfeld: In the aptly named episode "The Phone Message", after accidentally turning down sex on a date thinking it was just an invitation for coffee, George tries to rectify the situation by leaving a voicemail. Unfortunately, it is long, rambling, and embarrassing and he's afraid it makes him seem like an idiot. Against the advice from Jerry, George calls several times trying to clear up the matter, only to leave increasingly angry and hostile messages. Deciding she can never hear them, he and Jerry break into her apartment to erase them. They succeed only for George to learn that she had already heard them and thought they were a cute, funny joke.
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Phineas and Ferb: In "I, Brobot", Doofenshmirtz plans to hover over his girlfriend's house with a huge magnet so he can erase embarrassing messages he left on her voicemail.
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The Office (US): One scene in "Women's Appreciation" epitomises Cringe Comedy; Michael breaks up with Jan over voicemail, unaware that she is on her way to the office. When she comes in, Michael hangs up and pretends everything is fine. She tells him she wants to get back together, unaware of the voicemail. She sees she has a missed call from Michael and listens to it in front of him.
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Blades of Glory: Jeff tries to make it up to Jimmy by repeatedly leaving messages. Each voicemail he leaves is more desperate until eventually he is practically grovelling for Jimmy's forgiveness.
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Ellen in Leftover Soup leaves her ex-boyfriend and roommate such a voicemail when she finds out he's cheating on her. He promptly turns it into a Voice Clip Song titled "Answering Machine Bitch."
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Regular Show: Mordecai accidentally leaves a Pocket Dial message expressing his fondness for Margaret. After he realises, he and Rigby must find Margaret's phone to delete it before she listens to it.
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He's Just Not That into You:
Gigi tries to defy the stereotype that guys should call first by calling him first. However, her voicemail exudes desperation. Naturally, he doesn't call her back.
Mary is on the receiving end of one of these after she goes on a date with a guy who leaves her two. The first one is him singing a song with her name in it and asking for a follow-up date. Cute. The second one is him singing the exact same song, this time using the name Jenny and ending with him realizing he accidentally called the wrong number. Yikes.
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The Campaign: Senator Cam Brady, who is in the middle of a presidential campaign, accidentally leaves a rather explicit voicemail meant for his secret lover on the answering machine of a conservative Christian family. It obviously is leaked to the public and his polling numbers tank.
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I Love You, Man: In the bromance comedy, Peter leaves voicemails for Sydney asking to hang out. However, his awkwardness and poor social skills make it come across as pathetic.
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The SpongeBob SquarePants Movie: While King Neptune is interrogating Mr. Krabs about the disappearance of his crown, Plankton calls the Krusty Krab and gets picked up by the answering machine. Plankton uses the opportunity to imitate a nonexistent stranger who Mr. Krabs sold the crown to, claiming that he gave it to a guy in Shell City. Mr. Krabs frantically tries to silence the voicemail and eventually claims that it was a wrong number, only for Neptune to believe every word of the message.
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Mom: In one episode Christy leaves a particularly awkward voicemail for her daughter Violet.
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Workaholics: In the episode "Real Time", the boys must get to work to erase drunk and angry messages they left the night before on Alice's answering machine.
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In volume nine of The Case Files of Jeweler Richard, when Saul meets up with Seigi, he plays four increasingly panicked voicemails from Richard worrying about what trouble Seigi, a fully grown adult man, could get into in the six hours it would take Richard to fly there from Australia. Saul ignored all of them, despite Richard's desperate pleading for an immediate response and the fact that he was already looking up plane tickets.
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RWBY Chibi: In one skit, Jaune leaves Weiss a series of voicemails trying to ask her out on a study date. They become increasingly desperate and angry as she fails to return his calls, concluding in an angry rant about how much he hates her selfish, arrogant behavior. Right after he finishes that one, Weiss walks up to him and asks if he's seen her phone because she lost it somewhere and has been searching for it all afternoon.
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In one of Homestar Runner's "Marzipan's Answering Machine" videos, Homestar completely misunderstands a message Marzipan left with Pom-Pom for him as some kind of insult and sends her an angry breakup message in turn. After Pom-Pom clears things up, Homestar tries to erase his message by talking backward, then goes to Marzipan's house and steals the tape, replacing it with one of his own where he badly impersonates the other characters leaving the kind of messages they usually leave (including a bad impersonation of himself).
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Hey Arnold!: In "Helga Blabs It All", Helga goes to the dentist's office and while she's still delirious from laughing gas, she tries to call Arnold, whom she secretly has a crush on despite picking on him, to say she loves him, but it turns out she was actually speaking into his answering machine. When she realizes what she's done, she tries to get to the answering machine to take the message back before he gets to hear it.
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Crazy Ex-Girlfriend: Rebecca plays the spirit of the trope straight, if not the letter, when she accidentally sends a text intended for Paula (about her feelings for Josh) to Josh. Fortunately, she knows that he leaves his phone at home while he's at his martial arts practise, giving her time to break in and delete the message. Her entire office meeting agrees that this is the highest possible priority, and a judge gets her a police escort to Josh's building so that she can speed, while the other lawyers sing a glam rock song about this "Textmergency".
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How I Met Your Mother:
"Return of the Shirt" has Ted trying to reconcile with his ex-girlfriend Natalie. Initially bewildered on why she angrily hung up on him, he then realizes that he broke up with her over the phone, recorded on her answering machine, on her birthday, with her friends listening to it while they set up a surprise party for her. Lily calls Ted out over this immature method.
In the episode "How Lily Stole Christmas", Lily hears a voicemail from Marshall's answering machine where Ted calls her a "grinch" for breaking up with Marshall over the past summer. She feels insulted and takes down all the Christmas decorations.
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Friends:
A comedic subversion of the trope. In "The One Where No One's Ready", Monica hears a voicemail from her ex Richard asking her to call him back but she can't tell if it's old or new. Monica breaks into his voicemail and hears a message she assumes to be from a new lover, but is really from his daughter Michelle; she only finds this out by failing to discreetly prank call her. In an attempt to clear everything up, she breaks into his voicemail one last time, erases all of the messages, and leaves a new one where she apologizes and asks for forgiveness, blaming her period for making her act crazy. Except she unintentionally re-records Richard's outgoing voicemail message, humiliating herself.
In "The One Where Ross Finds Out", Rachel gets drunk one night on a date and tells him all about her feelings for Ross. The guy advises her to get "closure" by telling Ross she's over him. Rachel immediately calls Ross and leaves the message, unintentionally confessing that she has feelings for him. She doesn't fully remember this in the morning and is in the same room when Ross checks his voicemail, causing her to panic. It works out however since this leads to Ross breaking up with his current girlfriend Julie and kissing Rachel.
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Index of Shame
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Phone Tropes
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