History YMMV / TheFortyYearOldVirgin

* SeinfeldIsUnfunny
** While plenty of comedy movies and shows had had lots of improv before, this was the first mainstream comedy in which ''all'' of the dialogue was ad-libbed or retroscripted like a feature-length line-o-rama reel for [[CringeComedy deliberately awkward]] comedic effect, and was seen as a unique new way to do feature-film comedy in 2005. Now, it's impossible to find any live action comedy whatsoever that isn't created this way and by the middle of TheNewTens, the term "line-o-rama" became negatively associated with movies where comedians just ad lib poorly for 90 minutes.
** This was also the film that convinced major studios to [[AuteurLicense leave all creative decisions for feature-length comedies to the comedians]] rather than pairing them up with professional writers and directors. At the time, comedians being allowed to do what ''they'' thought was funny and clever was seen as a welcome break from the TotallyRadical gross-out comedies that studios had been pushing since the mid-90s. The result was two decades of comedy movies where ''every'' creative decision looked as though it'd been made on the fly, which eventually became seen as less daring and more unprofessional, if not self-indulgent.

** While the theme of the movie is that losing your virginity should be done with someone you care about, one can make the argument that the movie is also about toxic relationships and peer pressure.
*** Although Andy's friends are well-intentioned in trying to help Andy lose his virginity, it's clear that none of them actually respect women and they sound like they have never actually spoken to a real woman in their life (something Cal actually points out). For example, Jay plays porn in the store and makes derogatory comments about women that nearly causes Jill to leave him if Andy hadn't covered for him. Then there's the time when they try to convince him to have sex with a drunk woman.
*** When Cal advises Andy to be more confident and let women just talk about themselves, Andy has much more success and feels more confident after talking to Beth. When Andy meets Trish, he's more confident and they both unwittingly decide to take the relationship slow and it does become much more mature and romantic, with Andy even building a repertoire with her daughters, particularly Marla who's quick to catch on to how much happier he makes her mother. Even his friends realize in the end that Andy will be happier with Trish than with Beth and encourage him to go back to her.
** Another lesson that can be taken from the movie can be "While being socially awkward and shy around women isn't something to aspire to, it's not the worst thing you can be".
*** Although Andy is awkward in his attempts to seduce women, he's much more respectful of women than his friends as he doesn't objectify them in his goal to lose his virginity. For example, he tries to avoid embarrassing the woman whose breast slips out of her shirt. The problem was that he needed better advice on how to talk to women in a romantic sense and needed some confidence, things he was lacking before he met Trish.

*** When Cal advises Andy to be more confident and let women just talk about themselves, Andy has much more success and feels more confident after talking to Beth. When Andy meets Trish, he's more confident and they both unwittingly decide to take the relationship slow and it does become much more mature and romantic. Even his friends realize in the end that Andy will be happier with Trish than with Beth and encourage him to go back to her.

** Yes, that ''is'' Stormy Daniels as the porn star Andy [[ADateWithRosiePalms tries, and fails, to masturbate to.]] You know her now as the porn star linked to a UsefulNotes/DonaldTrump scandal.

* HilariousInHindsight:
** ''"What do I have to do for you to have sex with me? Do you want me to dress up like [[ComicBook/TheMightyThor Thor]]? I'll dress up like Thor!"'' Trish's teenage daughter is played by Creator/KatDennings, who went on to play Darcy Lewis in ''Film/{{Thor}}''. Andy also owns multiple ''[[ComicBook/TheAvengers Avengers]]'' action figures--which is pretty funny now that [[Creator/PaulRudd his coworker]] is Film/AntMan1.
** Seeing Kat Dennings go to a sex-counselling session seems ironic considering she would later play a recurring character in the sex-ed lesson disguised as a raunchy cartoon ''WesternAnimation/BigMouth''.
** Anyone who has seen ''Series/TheOfficeUS'' beforehand would probably get a kick out of seeing Mindy Kaling dealing with a clingy, deluded ex.
** Near the end, Cal walks in on Beth having ADateWithRosiePalms in the bathtub and it's implied that he hooks up with her. A few years later, Seth Rogen and Elizabeth Banks' characters have sex [[spoiler:and end up getting married]] in ''Film/ZackAndMiriMakeAPorno''.

* HarsherInHindsight:
** David saying he'd go on a killing spree if he had to listen to Michael [=McDonald=] one more time would probably be taken more seriously after countless public massacres in the following years.
** Andy's manager Paula flirts with him on a few occasions and tells the other guys she's sexually attracted to him. Nowadays that would be viewed as abusing her authority.

* CrossesTheLineTwice:
** You know how I know that you're gay? Because you've got a bumper sticker that says "I love having guy's balls in my face".
--> That's gay?!
** "You are fucking with the wrong nigga!" "Well, you're fucking with the wrong ''sand'' nigga!"

** [[AlternativeCharacterInterpretation This is arguable]]. At the beginning of the film, Andy is a severely introverted person who has let his anxieties turn him into someone who is so nervous about women that he can't seek a relationship or even ''masturbate'' without problems. The only real people he seems to spend time with for fun are his neighbors who he appears to spend only a short time with to watch a single show during the week. His coworkers don't even want to invite him to the poker game at first, but need to for a complete game. The screenplay even says about his workplace "it is clear he has no close relationships here". Yes, plenty of the things his coworkers push him to do are unhelpful or inappropriate, but they recognize that Andy is not living life to its fullest and want him to expand his horizons.
** The key element is that whatever his problems are, having sex will not magically take them away, and may actually make things worse. The other characters spend the whole movie demonstrating that. Even if what he ultimately needs is [[ThePowerOfFriendship good friends]] or [[ThePowerOfLove romance/intimacy]], [[TheFourLoves those are very different needs than sex]] but in a highly sexualized society with [[YouNeedToGetLaid one solution to every problem]] Andy wasn't able to see that.

* SignatureScene: Creator/SteveCarell getting his chest waxed.

** "Bags of sand" (the line that gives away Andy is a virgin) to refer to breasts.
*** It also enjoys second life as a reaction macro used against BlatantLies.
** You know how I know you're gay? You added this trope.
*** On many internet message boards, "You know how I know you're gay?" has become a typical comeback to somebody pointing out minor flaws on an otherwise attractive woman. Alternately, they'll just post a screenshot from the scene.
** "Hey buddy, got a big box of porn for ya!"
** "Putting the pussy on a pedestal."

** Another lesson that can be taken from the movie can be "While being socially awkward and shy around women isn't something to aspire to, a benevolent kind of awkwardness is far better than the perverted and sexist kind of awkwardness women are, unfortunately, more familiar with".

** Another lesson that can be taken from the movie can be "While being socially awkward around women isn't something to aspire to, a benevolent kind of awkwardness is far better than the perverted and sexist kind of awkwardness women are more familiar with".

*** Although Andy doesn't drive, Trish doesn't think less of him for riding a bicycle and often laughs at his awkward jokes about his empty home. Whereas, Jay's girlfriend, Jill, almost leaves Jay when she finds his awkward and derrogatory notes about the women at the speed dating event. Only staying with Jay because Andy took the blame for the notes while making sexist remarks to deter Jill's suspicions of Jay.

*** Although Andy is awkward in his attempts to seduce women, he's much more respectful of women than his friends as he doesn't objectify them in his goal to lose his virginity. For example, he tries to avoid embarrassing the woman whose breast slips out of her shirt. He just needed better advice and some confidence, things he was lacking before he met Trish.

*** Although Andy doesn't drive, Trish doesn't think less of him for it and laughs at his awkward jokes about his empty home. Whereas, Jay's girlfriend, Jill, almost leaves him when she finds his sexist notes on the speed dating event and only stayed with him because Andy took the blame.

** Another lesson that can be taken from the movie can be "While being socially awkward around women isn't something to aspire to, a benevolent kind of awkward is far better than the malicious, misogynistic, and sexist kind of awkwardness women are more familiar with". Although Andy is awkward, he's much more respectful of women than his friends and he doesn't objectify them in his goal to lose his virginity. Andy's hobbies are portrayed as unmanly and a sign of him being socially inept, however, many female critics have said that his hobbies and overall attitude towards women make him way more desirable than his friends as he's got a healthy lifestyle, he's in good shape, he's got hobbies he enjoys and finds fulfillment, and he's got a successful job.

* AlternateAesopInterpretation: While the theme of the movie is that losing your virginity should be done with someone you care about, one can make the argument that the movie is also about toxic relationships and peer pressure.
** Although Andy's friends are well-intentioned in trying to help Andy lose his virginity, it's clear that none of them actually respect women and they sound like they have never actually spoken to a real woman in their life (something Cal actually points out). For example, Jay plays porn in the store and makes derogatory comments about women that nearly causes Jill to leave him if Andy hadn't covered for him. Then there's the time when they try to convince him to have sex with a drunk woman.
** Andy's hobbies are portrayed as unmanly and a sign of him being socially inept, however, many female critics have said that his hobbies and overall attitude towards women make him way more desirable than his friends as he's got a healthy lifestyle, he's got hobbies he enjoys and finds fulfillment, and he's got a successful job.
** When Cal advises Andy to be more confident and let women just talk about themselves, Andy has much more success and feels more confident after talking to Beth. When Andy meets Trish, he's more confident and they both unwittingly decide to take the relationship slow and it does become much more mature and romantic. Even his friends realize in the end that Andy will be happier with Trish than with Beth and encourage him to go back to her.

* GenreTurningPoint: While comedy films in which comedians/actors made all of the creative decisions and ad libbed most of their scripts had existed before this one, they tended to be low-key indie cult films while the more popular studio comedies still used professional writers and directors (the first ''Film/AustinPowers'' film was a major exception). While the Apatow-produced ''Film/AnchormanTheLegendOfRonBurgundy'' was the first film that proved to the major studios that movies where comedians are more or less allowed to "go off" for 90 minutes could work on a larger scale, this was the one that made it the norm for the next two decades. It also displaced the trend of over-the-top gross-out films that had been the norm up to that point for a decidedly more naturalistic style.

** ''"What do I have to do for you to have sex with me? Do you want me to dress up like [[ComicBook/TheMightyThor Thor]]? I'll dress up like Thor!"'' Trish's teenage daughter is played by Creator/KatDennings, who went on to play Darcy Lewis in ''Film/{{Thor}}''. Andy also owns multiple ''[[ComicBook/The Avengers Avengers]]'' action figures--which is pretty funny now that [[Creator/PaulRudd his coworker]] is Film/AntMan1.