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Movies like Maybe If You... (2005)

The best movies like Maybe If You... (2005) are The Wedding Year (2019), Shane Gillis: Beautiful Dogs (2023) and Spa Weekend (2026). If Maybe If You... hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The Wedding Year (2019)

    A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.

    Why it matches: Recommended by TMDB viewers · both comedy

  2. 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
  3. Spa Weekend (2026)

    Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break, the women escape to a luxury spa retreat for an unforgettable weekend dedicated to fun, laughter, and a lot of really bad decisions.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  4. Ali Wong: Single Lady (2024)

    After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  5. Held Up (1999)

    What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.

    Why it matches: Recommended by TMDB viewers · both comedy

  6. Much Ado About Nothing (2013)

    A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  7. Class Rank (2017)

    Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  8. 72 HOURS (2026)

    To save his career, a 40-year-old ad exec joins a crew of twentysomethings for a wild Miami bachelor party after they mistakenly add him to a group chat.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  9. Chris Rock: Kill the Messenger (2008)

    An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing presidential campaign, the possibility of a black president, George W. Bush, gas prices, low-paid jobs, ringtones and bottled water, sex, relationships and the correct use of the n-word

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  10. Fun with Dick and Jane (1977)

    When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  11. Wet Hot American Summer (2001)

    It's the last day of Camp Firewood's season, but there's still time for the big talent show, a little romance… and for everyone to be wiped out by the piece of NASA's Skylab that's hurtling toward Earth.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  12. Malibu Rescue: The Next Wave (2020)

    It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on Malibu Beach. But when Team USA falls victim to a bout of food poisoning, it’s up to Tyler, Dylan, Eric, Lizzie and Gina to represent their country in the world's most extreme lifeguard challenge!

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  13. The Cocoanuts (1929)

    During the Florida land boom, the Marx Brothers run a hotel, auction off some land and thwart a jewel robbery.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  14. Fist Fight (2017)

    When one school teacher gets the other fired, he is challenged to an after-school fight.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  15. Don't Tell Mom the Babysitter's Dead (1991)

    Sue Ellen Crandell is a teenager eagerly awaiting her mother's summer-long absence. While the babysitter looks after her rambunctious younger siblings, Sue Ellen can party and have fun. But then the babysitter abruptly dies, leaving the Crandells short on cash. Sue Ellen finds a sweet job in fashion by lying about her age and experience on her résumé. But, while her siblings run wild, she discovers the downside of adulthood

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. Dylan Moran: Like, Totally (2006)

    Dylan Moran returns with an all-new stand-up show. Unpredictable, startling, bizarre, elegiac, but above all brilliant and hilariously funny, Moran is a master of comedy.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  17. After the Ball (2015)

    After the Ball, a retail fairy tale set in the world of fashion. Kate's dream is to design for couturier houses. Although she is a bright new talent, Kate can't get a job. No one trusts the daughter of Lee Kassell, a retail guru who markets clothes "inspired" by the very designers Kate wants to work for. Who wants a spy among the sequins and stilettos? Reluctantly, Kate joins the family business where she must navigate around her duplicitous stepmother and two wicked stepsisters. But with the help of a prince of a guy in the shoe department her godmother's vintage clothes and a shocking switch of identities, Kate exposes the evil trio, saves her father's company -- and proves that everyone can wear a fabulous dress.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. Sextuplets (2019)

    Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. The After Party (2018)

    When an aspiring rapper goes viral for the wrong reasons, he thinks his career is sunk. But a wild party gives him one more chance to make it right.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  20. Thunderstruck (2012)

    After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this

Like Maybe If You... and something else?

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

Frequently asked questions

What are the best movies like Maybe If You...?

The closest matches to Maybe If You... are The Wedding Year (2019), Shane Gillis: Beautiful Dogs (2023) and Spa Weekend (2026). Below are 17 more, each with the reason it matches.

What should I watch after Maybe If You...?

Start with The Wedding Year (2019), the closest match to Maybe If You....

What is the highest-rated movie like Maybe If You...?

Much Ado About Nothing (2013), rated 6.8/10 by 299 TMDB users.

What is the newest movie like Maybe If You...?

Spa Weekend (2026) is the most recent release on this list.

Are there English movies like Maybe If You...?

Yes: The Wedding Year (2019), Shane Gillis: Beautiful Dogs (2023) and Spa Weekend (2026).

How are movies similar to Maybe If You... chosen?

First come films that Trakt’s viewers watch alongside Maybe If You..., 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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