Movies like Winter Cherries 2 (1990)
The best movies like Winter Cherries 2 (1990) are Enemies, a Love Story (1989), Piter FM (2006) and Why Did I Get Married Again? (2026). If Winter Cherries 2 hooked you with its comedy and drama, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedIrreplaceable You (2018)7.0/10 from 736 votes
- NewestWhy Did I Get Married Again? (2026)Released 2026
Enemies, a Love Story (1989)
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisPiter FM (2006)
Masha, who works for a radio station, and Maxim, a street sweeper with an architectural degree, cross paths with each other when they are at an indecisive point in their lives.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisWhy Did I Get Married Again? (2026)
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisJack Goes Boating (2010)
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisNumb (2007)
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel, lesbian exercise classes and a dizzying variety of pills get him through the day, but don't quite solve his problem. His writing partner tries everything to get him back to normal, but it's not until Hudson meets Sara that he finds a real motivation to get better and to actually start feeling again. From the writer of Deuce Bigalow, comes NUMB, a romantic comedy following an unusual man looking for strange love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisThe Best You Can (2025)
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisCyrus (2010)
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisSitting in Bars with Cake (2023)
Extrovert Corinne convinces Jane, a shy, talented baker, to commit to a year of bringing cakes to bars, to help her meet people and build confidence. But when Corinne receives a life-altering diagnosis, the pair faces a challenge unlike anything they've experienced before.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Worth the HypeMovies like thisThe Giant Mechanical Man (2012)
An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisNothing Like the Holidays (2008)
It’s Christmastime and the far-flung members of the Rodriguez family are converging at their parents’ home in Chicago to celebrate the season and rejoice in their youngest brother’s safe return from combat overseas.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisIs This Thing On? (2025)
As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to navigate co-parenting, identity, and whether love can take a new form.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisYoung People Fucking (2007)
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisDelirious (2007)
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved with K'Harma Leeds, the hottest pop star of the moment, Les grows jealous and plots revenge.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisIrreplaceable You (2018)
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisMoscow on the Hudson (1984)
A Russian circus visits the US. A clown wants to defect, but doesn't have the nerve. His saxophone playing friend however comes to the decision to defect in the middle of Bloomingdales. He is befriended by the black security guard and falls in love with the Italian immigrant from behind the perfume counter. We follow his life as he works his way through the American dream and tries to find work as a musician.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisFather of the Bride (1950)
Proud father Stanley Banks remembers the day his daughter, Kay, got married. Starting when she announces her engagement through to the wedding itself, we learn of all the surprises and disasters along the way.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisNot Like Dad (2021)
The story of the journey of an adult hero to his Bata, a stern Russian peasant who became a father at the dawn of the nineties and raised his son the way all Soviet people did.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisHow to Please a Woman (2022)
When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Good House (2021)
When wry New England realtor Hildy Good rekindles a romance with her old high-school flame, Frank Getchell, it ignites long-buried emotions and family secrets that propel Hildy toward a reckoning with the one person she's been avoiding for decades: herself. Based on the best-selling novel by Ann Leary.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisBlind (2017)
A novelist is blinded in a car crash that killed his wife and several years later rediscovers his passion for life and writing when he embarks on an affair with the neglected wife of an indicted businessman.
Why it matches: Recommended by TMDB viewers · both drama & romance
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Frequently asked questions
What are the best movies like Winter Cherries 2?
The closest matches to Winter Cherries 2 are Enemies, a Love Story (1989), Piter FM (2006) and Why Did I Get Married Again? (2026). Below are 17 more, each with the reason it matches.
What should I watch after Winter Cherries 2?
Start with Enemies, a Love Story (1989), the closest match to Winter Cherries 2.
What is the highest-rated movie like Winter Cherries 2?
Irreplaceable You (2018), rated 7.0/10 by 736 TMDB users.
What is the newest movie like Winter Cherries 2?
Why Did I Get Married Again? (2026) is the most recent release on this list.
How are movies similar to Winter Cherries 2 chosen?
First come films that Trakt’s viewers watch alongside Winter Cherries 2, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.