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Movies like Waiting For Cupid (2025)

The best movies like Waiting For Cupid (2025) are Driver's Ed (2026), Held Up (1999) and Sextuplets (2019). If Waiting For Cupid hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Driver's Ed (2026)

    A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  2. 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

  3. 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
  4. Anuvahood (2011)

    Kenneth (who likes to call himself Kay) begins to realise he's just another wannabe bad boy... even less than a loser in fact. After quitting his job at Laimsbury's, Kay vows to become a respected gangster... or cry trying. A pulls-no-punches, coming-of-age story, centering on one directionless hopeless "shotter", who finds his true worth in the face of urban adversity.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  5. 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
  6. Jackass Presents: Bad Grandpa (2013)

    86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  7. The F**k-It List (2020)

    After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  8. 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
  9. Taking Care of Business (1990)

    An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  10. Seriously Single (2020)

    While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  11. Adventures in Public School (2018)

    A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  12. Mr. Bones (2001)

    A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  13. No Time for Sergeants (1958)

    Georgia farm boy Will Stockdale is about to bust with pride. He’s been drafted. Will’s ready. But is Uncle Sam ready for Will?

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  14. The Roast of Tom Brady (2024)

    Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  15. Babes (2024)

    After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. 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
  17. Yellow Mirror (2026)

    A defective lamp reveals a heartbreaking truth about what Homer believes is reality, and an AI-powered tablet befriends and controls Maggie. The Simpsons struggle to find the light through two dark tales of the curious and bizarre.

    Why it matches: Recommended by TMDB viewers · both comedy

    Absolute CinemaMovies like this
  18. Mr. Roosevelt (2017)

    A young woman returns home and must confront her ex-boyfriend when an unexpected tragedy occurs.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. 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
  20. The Climb (2020)

    Kyle and Mike are best friends who share a close bond — until Mike sleeps with Kyle’s fiancée. A stormy but enduring relationship ensues between Kyle, with limitless patience, and Mike, who only lives his life by sowing discord in that of others, across many years of laughter, heartbreak, and rage.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this

Like Waiting For Cupid and something else?

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

Frequently asked questions

What are the best movies like Waiting For Cupid?

The closest matches to Waiting For Cupid are Driver's Ed (2026), Held Up (1999) and Sextuplets (2019). Below are 17 more, each with the reason it matches.

What should I watch after Waiting For Cupid?

Start with Driver's Ed (2026), the closest match to Waiting For Cupid.

What is the highest-rated movie like Waiting For Cupid?

Sextuplets (2019), rated 6.2/10 by 886 TMDB users.

What is the newest movie like Waiting For Cupid?

Yellow Mirror (2026) is the most recent release on this list.

How are movies similar to Waiting For Cupid chosen?

First come films that Trakt’s viewers watch alongside Waiting For Cupid, 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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