Movies Like How, When, and with Whom
If you liked How, When, and with Whom (1969), a romance movie directed by Antonio Pietrangeli, 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 Matchmaker's Playbook (2018)
★ 7.1/10Also romanceAfter a career-ending accident, former NFL recruit Ian Hunter is back on campus, and he's putting his extensive skills with women to work as one of the masterminds behind a successful and secretive dating service. But…
- 2

It Was Always You (2021)
★ 7.3/10Also romanceElizabeth's engagement plans are thrown into disarray when her fiancée's free-spirited brother David returns home. David's unexpected influence prompts Elizabeth to question her life decisions.
- 3

Safe Haven (2013)
★ 7.2/10Also romanceA young woman with a mysterious past lands in Southport, North Carolina where her bond with a widower forces her to confront the dark secret that haunts her.
- 4

A Godwink Christmas: Meant For Love (2019)
★ 7.1/10Also romanceMultiple coincidences and a chance meeting bring together Alice and Jack, two strangers from very different family backgrounds, for an unexpected Christmastime courtship filled with personal revelations, misread…
- 5

Gabriel's Rapture: Part I (2021)
★ 7.8/10Also romanceIn the fourth instalment of the Gabriel's Inferno series, Professor Gabriel Emerson has embarked on a passionate, yet clandestine affair with his former student Julia Mitchell, but when they return from their romantic…
- 6

A Little Christmas Charm (2020)
★ 6.9/10Also romanceHolly, a jewelry designer finds a lost charm bracelet and teams up with investigative reporter Greg in hopes of finding the owner and returning it by Christmas Eve.
- 7

Paris, Wine & Romance (2019)
★ 6.9/10Also romanceIsabella is the ambitious new owner of her family’s Oregon winery whose dream of becoming world-renowned takes a big step forward when she enters a prestigious wine competition in Paris. Upon arrival, Isabella meets…
- 8

Gabriel's Rapture: Part III (2022)
★ 7.9/10Also romanceIn the sixth installment of the Gabriel's Inferno series, Julia deals with the aftermath of Gabriel's departure, while Gabriel goes on a journey of self-discovery. Will they reunite and be able to repair what is broken?
- 9

Not Cinderella's Type (2018)
★ 6.8/10Also romanceIndy lives with her aunt and uncle and believes her life is fine until an accident brings a new guy into her life. Bryant Bailey is not Indy's type - she's never been into guys like him. But then again, she's never…
- 10

A Gift to Remember (2017)
★ 6/10Also romanceAfter colliding with a pedestrian on her bicycle who loses his memory following the accident, Darcy Archer becomes determined to help the handsome guy figure out who he is. In the process, she finds out a lot more…
- 11

Sisters of the Groom (2017)
★ 6.5/10Also romanceWhen Sarah needs to impress a corporate bigwig in order to help her sister's catering business, she finds herself agreeing to be his son’s pretend date to a family wedding
- 12

Rome in Love (2019)
★ 6.3/10Also romanceAn unknown actress lands the role of a lifetime in Rome. Paired with an American journalist writing a profile, she will discover surprises about love and life in the eternal city.
- 13

A Royal Christmas (2014)
★ 6.7/10Also romanceA young working girl with a blue-collar background is surprised when her new fiancé announces he is actually a prince of a small sovereign country in Europe. After the couple quickly takes off to spend the holidays at…
- 14

Christmas Made to Order (2018)
★ 6.1/10Also romanceWhen architect and Christmas amateur Steven finds himself hosting his family for Christmas, he recruits holiday coordinator Gretchen to bring holiday joy to his home. Gretchen’s expert Christmas spirit brings Steven’s…
- 15

The Laughing Woman (1969)
★ 6.7/10Also romanceBeautiful PR woman, Maria finds herself trapped in the home of the sinister and troubled Dr. Sayer, where she is subjected to a series of increasingly bizarre, terrifying, and degrading sex games. Sayer admits that he…
- 16

Gabriel's Rapture: Part II (2022)
★ 8.1/10Also romanceIn the fifth installment of the Gabriel's Inferno series, Gabriel and Julia’s happiness is threatened by a conspiring student and academic politics. When Gabriel is confronted by the university administration, will he…
- 17

Holiday Date (2019)
★ 6.5/10Also romanceWhen Brooke’s boyfriend, Ethan, breaks up with her just before the holidays, she agrees to go home with Joel, an actor who will pose as her boyfriend.
- 18

June and John (2025)
★ 6.1/10Also romanceJohn leads an ordinary life with a monotonous routine. One day John runs into a woman on the subway who is as beautiful as she is mysterious named June. His encounter with her finally leads him to have a goal in his…
- 19

Valentine in the Vineyard (2019)
★ 6.1/10Also romanceAs partners in life and professional winemaking, Frankie Baldwin and Nate DeLuca have different personality types and styles. They’ve just gotten engaged when Frankie’s cousin Lexi and Nate’s brother Marco spring the…
- 20

Chateau Christmas (2020)
★ 6.1/10Also romanceMargot, a world-renowned pianist, returns to Chateau Newhaus to spend the holidays with her family and is reunited with an ex who helps her rediscover her passion for music.