Movies Like Pining for Douglas

If you liked Pining for Douglas (2026), a movie, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
The Best Man Holiday (2013)
★ 6.5/10
When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.
2
You've Got Mail (1998)
★ 6.7/10
Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet—both blissfully unaware that he's trying to put her out of business.
3
Champagne Problems (2025)
★ 6/10
A driven American exec heads to Paris determined to acquire a champagne brand by Christmas — and accidentally falls for the heir to the bubbly empire.
4
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
5
One Day (2011)
★ 7.4/10
After spending the night together on the eve of their college graduation, Dexter and Emma are shown each year on the same date to see where they are in their lives. They are sometimes together, and sometimes not.
6
Tyler Perry's Finding Joy (2025)
★ 6/10
Joy, a successful designer, seeks a proposal at Christmas. In Wyoming's mountains, she finds what she truly needs when the man she loves sees her as just a friend.
7
The Hating Game (2021)
★ 7.3/10
Resolving to achieve professional success without compromising her ethics, Lucy embarks on a ruthless game of one-upmanship against cold and efficient nemesis Joshua, a rivalry that is complicated by her growing…
8
Love Is in the Air (2023)
★ 6.2/10
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
9
The Family Man (2000)
★ 6.8/10
Jack's lavish, fast-paced lifestyle changes one Christmas night when he stumbles into a grocery store holdup and disarms the gunman. The next morning he wakes up in bed lying next to Kate, his college sweetheart he…
10
Voicemails for Isabelle (2026)
★ 8.3/10
A young woman's hilariously confessional voicemails to her late sister are unknowingly redirected to a stranger, who begins to fall in love from afar.
11
Just Friends (2005)
★ 6.2/10
While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into a ferocious womanizer.
12
EXmas (2023)
★ 6.4/10
When Graham decides to surprise his family by traveling home for Christmas, he is shocked to discover them already celebrating with an unexpected guest of honor, his ex-fiancée, Ali. The two exes battle it out to see…
13
The Kissing Booth 2 (2020)
★ 7.6/10
With college decisions looming, Elle juggles her long-distance romance with Noah, changing relationship with bestie Lee and feelings for a new classmate.
14
Merry Matrimony (2015)
★ 5.8/10
Brie Traverston is up for partner at her firm if she can successfully coordinate a Christmas wedding reshoot and ignore all the feelings that come with working with the one-that-got-away Eddie Chapman and his possibly…
15
Seriously Single (2020)
★ 6.8/10
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.
16
The Map That Leads to You (2025)
★ 6.7/10
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life…
17
A Hollywood Christmas (2022)
★ 6.1/10
Jessica, a young, up-and-coming filmmaker in Hollywood has made a name for herself directing Christmas movies. But when handsome network executive Christopher shows up threatening to halt production on her latest…
18
Love Hard (2021)
★ 6.9/10
An LA girl, unlucky in love, falls for an East Coast guy on a dating app and decides to surprise him for Christmas, only to discover that she's been catfished. But the object of her affection actually lives in the same…
19
Looking for Eric (2009)
★ 6.5/10
Middle-aged postman and football fan Eric Bishop struggles with his increasingly chaotic existence, but receives some life coaching from the famously philosophical Éric Cantona.
20
Your Place or Mine (2023)
★ 6.3/10
When best friends and total opposites Debbie and Peter swap homes for a week, they get a peek into each other's lives that could open the door to love.