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Movies like Dating 101 (2008)

The best movies like Dating 101 (2008) are Shane Gillis: Beautiful Dogs (2023), Hard to Die (1990) and Goltzius & the Pelican Company (2012). If Dating 101 hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Shane Gillis: Beautiful Dogs (2023)

    In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  2. Hard to Die (1990)

    While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series of killings six months previously, is at the bottom of the whole thing. Little do they know the real horror that they face in the end.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  3. Goltzius & the Pelican Company (2012)

    Hendrik Goltzius, a late-16th-century Dutch printer and engraver of erotic prints, seduces the Margrave of Alsace into paying for a printing press to make and publish illustrated books.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  4. Pretty Persuasion (2005)

    A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.

    Why it matches: Recommended by TMDB viewers · both comedy

  5. Bill Burr: Drop Dead Years (2025)

    In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  6. Ricky Gervais: Mortality (2025)

    Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  7. Ricky Gervais: Armageddon (2023)

    Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  8. Jeff Dunham: Arguing with Myself (2006)

    A recorded live performance of ventriloquist Jeff Dunham portrays a comedian whose revival of an old-fashioned art has made ventriloquism more relevant to modern societal concerns. Starring his six main characters, from Bubba Jay, a Nascar-obsessed hick, to Peanut, a flamboyant gay monkey, Dunham’s puppets have dirty but inoffensive senses of humor that mock the American Dream.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  9. Jimmy Carr: Natural Born Killer (2024)

    Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  10. Louis C.K.: Oh My God (2013)

    Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for writing on his acclaimed show on FX, Louie. Performed in the round in front of a live audience, he discusses such topics as the food chain, animals, divorce, strange anecdotes, broken morality, murder and mortality.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  11. Accident Man: Hitman's Holiday (2022)

    The Accident Man is back, and this time he must best the top assassins in the world to protect the ungrateful son of a mafia boss, save the life of his only friend and rekindle his relationship with his maniacal father figure.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  12. Dave Chappelle: The Unstoppable... (2025)

    Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  13. The Horse's Mouth (1958)

    Gulley Jimson is a boorish aging artist recently released from prison. A swindler in search of his next art project, he hunkers down in the penthouse of would-be patrons the Beeders while they go on an extended vacation; he paints a mural on their wall, pawns their valuables and, along with the sculptor Abel, inadvertently smashes a large hole in their floor. Jimson's next project is an even larger wall in an abandoned church.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  14. Accident Man (2018)

    Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  15. Who Is Cletis Tout? (2001)

    With a hitman’s gun aimed at him, Finch tells the story of how he broke out of jail, fell in love, and took the identity of a man wanted by the Mafia.

    Why it matches: Recommended by TMDB viewers · both comedy

  16. Jimmy Carr: Telling Jokes (2009)

    Jimmy Carr delivers more of his cynical take on life's little absurdities in his trademark deadpan style in this live stand-up release. Jimmy unleashes his rapid-fire joke-telling and razor-sharp wit on topics ranging from religion and sex, to bullying and political correctness. Those brave enough to heckle are quickly put in their place by an array of colourful if brutal put-downs.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  17. Orgazmo (1998)

    A devout Mormon living in L.A. becomes a pornographic actor after his martial arts moves impress a big-time director.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. Ricky Gervais Live: Animals (2003)

    Ricky Gervais entertains a live audience in his first stand-up routine.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  19. Novocaine (2001)

    A dentist finds himself a murder suspect after a sexy patient seduces him into prescribing her drugs.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  20. South Park (Not Suitable for Children) (2023)

    After it's discovered that a teacher at South Park Elementary has an OnlyFans page, Randy is compelled to take a closer look at the seedy underbelly of the world of online influencers.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  21. Saving Silverman (2001)

    A pair of buddies conspire to save their best friend from marrying the wrong woman, a cold-hearted beauty who snatches him from them and breaks up their Neil Diamond cover band.

    Why it matches: Similar story and style · both comedy

  22. Mystic Pizza (1988)

    Three teenage girls come of age while working at a pizza parlor in Mystic, Connecticut.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  23. Deliver Us from Eva (2003)

    Eva Dandridge has been in charge of her younger sisters ever since their parents died many years ago. She is a very uptight young woman who constantly meddles in the affairs of her sisters and their significant others. Her brothers-in-law, who are tired of Eva interfering in their lives, decide to set her up with someone so she can leave them alone. They end up paying Ray, the local "playboy," $5,000 to date her. The plan goes by smoothly, but trouble comes when Ray actually falls in love with Eva.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  24. Heavy Flow (2017)

    Her boyfriend sucks... blood. A short horror-comedy about dating the undead.

    Why it matches: Similar story and style · both comedy

  25. The Jerk Theory (2009)

    An aspiring recording artist, Adam, is burned by a bad relationship experience and decides that if women won't respond to the "nice guy" then he'll be "the jerk." This is wildly successful with meaningless relationships, but when Adam meets and falls for Molly, who doesn't fall for his jerk routine, Adam is forced to reconsider his dating philosophy.

    Why it matches: Similar story and style · both comedy

  26. She's Out of My League (2010)

    When he starts dating drop-dead gorgeous Molly, insecure airport security agent Kirk can't believe it. As his friends and family share their doubts about the relationship lasting, Kirk does everything he can to avoid losing Molly forever.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  27. Mannequin Two: On the Move (1991)

    Although Jason works as a department store clerk, he is also a reincarnated prince. Long ago, his beloved Jessie was snatched away from him by an evil wizard who used his powers to transform her into wooden statue. Now Jessie is in Jason's department store as a mannequin. When he encounters her, she awakens from her thousand-year sleep. They quickly revive their romance, but the evil wizard has been reincarnated as well, and he's up to no good.

    Why it matches: Similar story and style · both comedy

  28. False Hopes (2020)

    Ace photographer Thomas McKenzie's been seeking the perfect girl his entire life - yet when two women simultaneously capture his interest, he learns he may not have been seeking the kind of love which truly makes us whole.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  29. Eye of the Beholder (2025)

    After an oblivious young man ineptly tells his date that she looks like a Picasso painting, an eccentric art curator attempts to teach him the true meaning of art.

    Why it matches: Similar story and style · both comedy

  30. Brown Sugar (2002)

    Sidney and Dre can attribute their lifelong friendship and the launch of their careers to one single childhood instant... witnessing the birth of hip-hop on a New York street corner. Now some 15 years later, she is a revered music critic at a national magazine and he is a successful, though unfulfilled, hip-hop record company executive. Both come to realize that their true life passions will only be fulfilled by remembering what they learned that day on the corner.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this

Like Dating 101 and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Dating 101?

The closest matches to Dating 101 are Shane Gillis: Beautiful Dogs (2023), Hard to Die (1990) and Goltzius & the Pelican Company (2012). Below are 27 more, each with the reason it matches.

What should I watch after Dating 101?

Start with Shane Gillis: Beautiful Dogs (2023), the closest match to Dating 101.

What is the highest-rated movie like Dating 101?

Louis C.K.: Oh My God (2013), rated 7.6/10 by 229 TMDB users.

What is the newest movie like Dating 101?

Ricky Gervais: Mortality (2025) is the most recent release on this list.

Are there English movies like Dating 101?

Yes: Shane Gillis: Beautiful Dogs (2023), Hard to Die (1990) and Goltzius & the Pelican Company (2012).

How are movies similar to Dating 101 chosen?

First come films that Trakt’s viewers watch alongside Dating 101, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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