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Movies like You Know the Drill (2025)

The best movies like You Know the Drill (2025) are Sierra Burgess Is a Loser (2018), Love, Guaranteed (2020) and How to Lose a Guy in 10 Days (2003). If You Know the Drill hooked you, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Sierra Burgess Is a Loser (2018)

    A case of mistaken identity results in unexpected romance when the most popular girl in high school and the biggest loser must come together to win over their crushes.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  2. Love, Guaranteed (2020)

    A lawyer takes on a new client that wants to sue a dating website because it guarantees love.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  3. How to Lose a Guy in 10 Days (2003)

    It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and running in this irresistible tale of sex, lies and outrageous romantic fireworks!

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  4. Rocky IV (1985)

    Rocky Balboa holds the world heavyweight championship, but a new challenger has stepped forward: Drago, a six-foot-four, 261-pound fighter who has the backing of the Soviet Union. This time, Rocky's training regimen takes him to Siberia, where he prepares for a globally televised match in the heart of Moscow. But nothing can truly prepare him for what he's about to face – a fight to the finish, in which he must defend not only himself, but also the honor of his country!

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  5. The Main Event (2020)

    An 11-year-old aspiring wrestler enters a competition to become the next WWE superstar by using special powers from a magical mask.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  6. Two Can Play That Game (2001)

    Corporate overachiever and all-around fly chick Shanté Smith thinks she's got the goods to keep her slickster boyfriend Keith, from straying—until he discovers a greener pasture, Shanté's archrival, Conny. Scorned, she plans to get her man back by any means necessary.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  7. Nothing (2003)

    After a terrible day, two good friends and housemates find the outside world converted into a featureless and empty white void.

    Why it matches: Recommended by TMDB viewers

  8. My Sassy Girl (2008)

    A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  9. Vicious (2025)

    When Polly receives a mysterious box, it comes with one rule: place inside something she needs, something she hates, and something she loves. If she doesn’t obey, it will consume everything—and everyone—she’s ever known.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  10. Players (2024)

    New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  11. The Wrong Paris (2025)

    Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  12. Only You (1994)

    Two childhood paranormal incidents have convinced schoolteacher Faith Corvatch that her true love is a guy named 'Damon Bradley', but she has yet to meet him. Preparing to marry podiatrist Dwayne in ten days, Faith receives a phone call from Dwayne's old classmate Damon Bradley, who is on his way to Venice. She impulsively decides to fly to Italy with the hope of finally encountering the man of her dreams. Accompanying her on the trip is her sister-in-law and best friend Kate, who has just left her husband, Faith's brother Larry.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  13. John Tucker Must Die (2006)

    After discovering they are all dating the same same guy, three popular students from different cliques band together for revenge, so they enlist the help of a new gal in town and conspire to break the jerk's heart, while destroying his reputation.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  14. Crossing Delancey (1988)

    Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is courted by a married, worldly author, Anton, yet can't seem to shake the down-to-earth appeal of Sam, a pickle vendor.

    Why it matches: Recommended by TMDB viewers

  15. The Night Before (1988)

    A popular beauty surprisingly asks a nerd to take her to the prom. He wakes up hours later in a sleazy alley. She's missing but he remembers nothing about it.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  16. School for Scoundrels (1960)

    Hapless Henry Palfrey is patronised by his self-important chief clerk at work, ignored by restaurant waiters, conned by shady second-hand car salesmen, and, worst of all, endlessly wrong-footed by unspeakably rotten cad Raymond Delauney who has set his cap at April, new love of Palfrey's life. In desperation Henry enrolls at the College of Lifemanship to learn how to best such bounders and win the girl.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  17. There's Something About Mary (1998)

    For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy detective he hired to find her.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  18. Office Romance (2026)

    Jackie, President and CEO of Air Cruz, runs a tight ship in her business, including a rigid anti-fraternization policy for all her employees. When a new sexy lawyer begins working for her, that policy becomes very tested.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  19. I Feel Pretty (2018)

    A head injury causes a woman to develop an extraordinary amount of confidence and believe she's drop dead gorgeous.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  20. One Night Only (2026)

    Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this

Like You Know the Drill and something else?

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

Frequently asked questions

What are the best movies like You Know the Drill?

The closest matches to You Know the Drill are Sierra Burgess Is a Loser (2018), Love, Guaranteed (2020) and How to Lose a Guy in 10 Days (2003). Below are 17 more, each with the reason it matches.

What should I watch after You Know the Drill?

Start with Sierra Burgess Is a Loser (2018), the closest match to You Know the Drill.

What is the highest-rated movie like You Know the Drill?

Rocky IV (1985), rated 7.1/10 by 5,052 TMDB users.

What is the newest movie like You Know the Drill?

One Night Only (2026) is the most recent release on this list.

How are movies similar to You Know the Drill chosen?

First come films that Trakt’s viewers watch alongside You Know the Drill, 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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