The Best Romantic Movies Set In Boston, Ranked

Ranker Film
Updated May 2, 2024 13 items
Voting Rules
The romantic movie must be primarily set in Boston.

When you think of Boston, you probably think of Boston Commons, the Paul Revere House, or maybe the John Hancock Tower. Romantic movies based in Boston show that you should also think about love when you think of the city. It has been the location for some very romantic films. The city's photogenic nature makes it a natural for a love story, which filmmakers have obviously realized.

What are the best romantic movies set in Boston? You get to choose. Vote up the ones that touched your heart the most. Did we miss any films showing Boston's romantic side? If so, add it to the list so others can weigh in. 

  • Good Will Hunting
    1

    Good Will Hunting

    Matt Damon, Robin Williams, Ben Affleck
    14 votes

    For Fans Of: Dead Poets Society, A Beautiful Mind, Ordinary People, Finding Forrester, The Perks of Being a Wallflower
    Why Should I Watch Good Will Hunting: This Oscar-winning drama showcases the passionate love story between a janitor at MIT and a Harvard student, set against the backdrop of beautiful Boston. The film expertly weaves together themes of self-discovery, emotional vulnerability, and intellectual challenges that captivate viewers from start to finish. With outstanding performances by Matt Damon, Robin Williams, and Minnie Driver, it's an essential watch for fans of romance with depth.

    In the heart of Boston, a self-taught genius janitor, Will Hunting (Matt Damon), solves complex mathematical problems at MIT unnoticed. His talents are discovered by Professor Gerald Lambeau (Stellan Skarsgård). The professor seeks therapy for Will's emotional issues from Sean Maguire (Robin Williams), an empathetic psychologist. As Will grapples with his past and future, he finds solace in his relationship with Skylar (Minnie Driver), a Harvard student. Good Will Hunting, a compelling drama directed by Gus Van Sant, won two Academy Awards including Best Original Screenplay.
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  • Fever Pitch
    2

    Fever Pitch

    Drew Barrymore, Jimmy Fallon, James B. Sikking
    19 votes

    For Fans Of: Moneyball, Bull Durham, Field of Dreams, The Natural, Major League
    Why Should I Watch Fever Pitch: This charming romantic comedy features Jimmy Fallon as a die-hard Red Sox fan who falls in love with Drew Barrymore's character amidst the excitement of the 2004 baseball season in Boston. The movie explores the delicate balance between dedication to one's passions and commitment to a relationship while celebrating Beantown's historic sporting culture. It's perfect for those seeking laughter and heart in equal measure.

    In Fever Pitch, an unconventional romantic comedy, Ben Wrightman (Jimmy Fallon), a die-hard Boston Red Sox fan, falls head over heels for the successful workaholic Lindsay Meeks (Drew Barrymore). Their romance blossoms amidst the backdrop of a thrilling baseball season. However, when his beloved team makes it to the playoffs, Ben's fanaticism puts their relationship to the test. Directed by Peter Farrelly and Bobby Farrelly, this film is a delightful blend of sports fervor and heartwarming romance, showcasing the hilarious yet poignant struggle between love and loyalty.
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  • What's Your Number?
    3

    What's Your Number?

    Anna Faris, Chris Evans, Ari Graynor
    13 votes

    For Fans Of: 27 Dresses, Friends with Benefits, He's Just Not That Into You, The Proposal, How to Lose a Guy in 10 Days
    Why Should I Watch What’s Your Number?: Anna Faris and Chris Evans light up this quirky rom-com set in Boston where Faris' character revisits her past relationships to find true love. Along with its lush cityscapes that showcase iconic neighborhoods like Beacon Hill, this film examines themes of vulnerability, acceptance, and finding happiness within oneself before embarking on love with someone else. It's witty, entertaining, and offers valuable life lessons for anyone navigating modern dating.

    Ally Darling (Anna Faris) is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.
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  • Next Stop Wonderland
    4

    Next Stop Wonderland

    Hope Davis, Alan Gelfant, Victor Argo
    6 votes

    For Fans Of: Sliding Doors, Serendipity, Amelie, Eternal Sunshine of the Spotless Mind, Garden State
    Why Should I Watch Next Stop Wonderland: This understated indie gem tells the tale of two strangers searching for meaning in their lives as they unknowingly cross paths throughout Boston streets and subway stations. With its poetic narrative style intertwined with elements of fate, chance encounters, and missed connections, it celebrates the mysterious beauty of unexpected romance in a bustling city environment. For admirers of artfully crafted stories infused with tenderness and longing; don't miss this enchanting journey.

    Boston residents nurse Erin Castleton (Hope Davis) and marine biology student Alan Monteiro (Alan Gelfant) don't know each another, but they share a frustration: their romantic lives. Having split with boyfriend Sean, Erin is unwillingly back on the market thanks to her mother, who places a singles ad in Erin's name. Scrambling for cash to repay a debt, Alan has little time for love. They almost meet on a train and at an aquarium. When they finally do meet, will they hit it off?
  • Love, Rosie
    5

    Love, Rosie

    Lily Collins, Sam Claflin, Christian Cooke
    7 votes

    For Fans Of: One Day, About Time, Me Before You, The Time Traveler's Wife, When Harry Met Sally
    Why Should I Watch Love, Rosie: This touching coming-of-age story follows two close friends navigating the complexities of life, love, and missed opportunities over 12 years in both Boston and England. As they traverse continents, viewers are treated to a poignant examination of timing and the power of true connection that withstands distance and time. With its stunning cinematography and brilliant performances by Lily Collins and Sam Claflin, this bittersweet romance will linger long after the credits roll.

    Rosie and Alex are best friends until Alex's family moves to America. They gamble everything to keep their love and friendship alive over the years and miles.
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  • Here Comes the Groom
    6

    Here Comes the Groom

    Bing Crosby, Jane Wyman, Franchot Tone
    5 votes

    For Fans Of: Going My Way, The Bells of St. Mary's, It Happened One Night, An Affair to Remember, Father of the Bride
    Why Should I Watch Here Comes the Groom: This classic Hollywood musical boasts a star-studded cast led by Bing Crosby and Jane Wyman as former lovers reuniting in post-WWII Boston amidst preparation for Wyman's wedding to another man. The film features timeless tunes that capture the essence of romance while exploring themes of loyalty, second chances, and following one's heart. It's an essential watch for those seeking a nostalgic glimpse into old-school charm.

    Reporter Pete Garvey (Bing Crosby), who has been running a French orphanage, is hoping to adopt two kids and marry his longtime girlfriend, Emmadel (Jane Wyman). But Pete, who has been dragging his feet on proposing, is unpleasantly surprised when he arrives in Boston ready to pop the question, only to find that Emmadel is engaged to another man (Franchot Tone). Desperate to win her back, Pete teams up with her cousin, Winifred, to convince Emmadel to finally marry him.
  • The Bostonians
    7

    The Bostonians

    Christopher Reeve, Vanessa Redgrave, Madeleine Potter
    4 votes

    For Fans Of: A Room with a View, Howards End, The Portrait of a Lady, Sense and Sensibility, Age of Innocence
    Why Should I Watch The Bostonians: Set in 19th-century Boston, this Merchant Ivory adaptation of Henry James' novel features a love triangle amongst the city's elite, marked by the struggle between traditionalism and progressive ideals. With its picturesque period setting, exquisite costume design, and enthralling exploration of gender roles and societal expectations within the context of romance, this film offers both a compelling story and rich historical insight into an era.

    Based on Henry James' novel, Merchant-Ivory's The Bostonians tells the story of Olive Chancellor, a 19th-century Boston woman dedicated to the suffrage movement who takes Verena Tarrant, a radical young woman, under her wing. But her cousin, is a male chauvinist who wants to marry and domesticate the young woman and a battle of wills ensues over her future.
  • Starting Over
    8

    Starting Over

    Burt Reynolds, Jill Clayburgh, Candice Bergen
    4 votes

    For Fans Of: An Unmarried Woman, Kramer vs. Kramer, Hannah and Her Sisters, Modern Romance, Broadcast News
    Why Should I Watch Starting Over: A fresh start is at the core of this dramedy featuring Burt Reynolds as a newly divorced man embarking on new relationships in his adopted city of Boston. The film delves into themes like self-discovery and reinvention with humor while showcasing prominent local landmarks like Quincy Market and Fenway Park. Fans of romantic comedies with depth will appreciate this tale about finding love amid life's many detours.

    When his wife, Jessica (Candice Bergen), leaves him for a chance at a music career, Phil Potter (Burt Reynolds) is devastated. He moves from New York City to Boston, joins a club for divorced men and cautiously begins an affair with a free-spirited schoolteacher named Marilyn (Jill Clayburgh), who genuinely seems to care about him. But when Jessica decides she wants Phil back, he jumps at the chance, only to wonder if perhaps he's made the wrong choice.
  • My Best Friend's Girl
    9

    My Best Friend's Girl

    Dane Cook, Kate Hudson, Jason Biggs
    8 votes

    For Fans Of: Something Borrowed, Failure to Launch, Wedding Crashers, Hitch, Just Friends
    Why Should I Watch My Best Friend’s Girl: Kate Hudson stars alongside Dane Cook in this irreverent rom-com where a jilted lover enlists his cynical friend to sabotage his ex-girlfriend's dates in hopes she'll realize her mistake – all set against the vibrant backdrop of contemporary Boston nightlife. The movie showcases an unorthodox approach to romance through witty banter, wild antics, and a surprising twist that keeps viewers entertained throughout. It's ideal for those seeking humor and an unconventional take on modern love.

    Lovestruck Dustin (Jason Biggs) is dating Alexis (Kate Hudson), his ideal girlfriend, but when she dumps him for coming on too strong, Dustin takes drastic measures to win her back. He asks his pal Tank (Dane Cook) to take her on a horrible date so that she will come running back to him, and Tank happily agrees. However, Alexis is more than a match for Tank's shock tactics, leaving him torn between loyalty to Dustin and a growing attraction toward Alexis.
  • Once Around
    10

    Once Around

    Richard Dreyfuss, Holly Hunter, Danny Aiello
    2 votes

    For Fans Of: Moonstruck; Terms of Endearment; Home for the Holidays; Steel Magnolias; Parenthood
    Why Should I Watch Once Around: Holly Hunter shines in this heartfelt dramedy about a young woman who falls for an eccentric businessman played by Richard Dreyfuss against her family's wishes as they navigate life together in suburban Boston. The film offers a poignant exploration of relationships within families and discovering happiness in unconventional places while still capturing the charm of its Massachusetts setting. For fans that appreciate stories rooted in familial bonds interwoven with themes of acceptance and personal growth, don't skip this underrated gem.

    Renata Bella (Holly Hunter) has no career prospects, her fiancé just broke up with her and she still lives with her parents although she is in her 30s. Desperate for direction in life, she attends a seminar on real estate sales. There she meets the brash, successful and arrogant salesman Sam Sharpe (Richard Dreyfuss). The two marry, but the brash quality that attracted her to Sam is off-putting her family, particularly with her strong-willed father, Joe (Danny Aiello).
  • The Promise
    11

    The Promise

    Kathleen Quinlan, Stephen Collins, Beatrice Straight
    2 votes

    For Fans Of: The Notebook; Dear John; The Lucky One; Atonement; Legends of the Fall
    Why Should I Watch The Promise: Set amidst the majesty of Boston's architecture and history, this 1979 romantic drama explores the complexities of love, loss, and personal identity as two individuals grapple with the consequences of a life-changing accident. Starring Kathleen Quinlan and Stephen Collins at their most vulnerable, this film is both heartrending and inspiring in its examination of how love can endure even the most trying circumstances. If you're seeking an emotionally charged journey into the depths of human connection, look no further.

    Two college students, Nancy McAllister (Kathleen Quinlan) and Michael Hillyard (Stephen Collins), want to marry. But Hillyard comes from a wealthy family and his mother, Marion (Beatrice Straight), disapproves of their relationship. Then the couple are in a car accident that leaves Nancy disfigured and Michael in a coma. Marion offers to pay for Nancy's reconstructive surgery if she moves away and promises never to contact Michael. Nancy painfully agrees. Will their paths ever cross again?
  • Between the Lines
    12

    Between the Lines

    John Heard, Lindsay Crouse, Jeff Goldblum
    2 votes

    For Fans Of: All the President's Men, Spotlight, The Paper, Zodiac, Shattered Glass
    Why Should I Watch Between the Lines: For fans of well-crafted ensemble pieces, this 1977 comedy-drama set around an alternative newspaper in Boston during its heyday offers a captivating mix of romance, humor, and social commentary. With a remarkable cast that includes Jeff Goldblum and John Heard, viewers are treated to a slew of unusual relationships and heartwarming stories unfolding amidst the cultural turbulence of the late '70s. It's ideal for those who appreciate authentic character-driven narratives.

    At the offices of a Boston alternative newspaper, the staff members enjoy a positive and open-minded work environment. Music critic Max (Jeff Goldblum) uses his influence to score dates, while news reporter Harry (John Heard) is dating the lovely Abbie (Lindsay Crouse), the publication's lead photographer. However, it seems as though their relatively carefree days are numbered when the owner of a major publishing company buys the paper, leading to more money, but even more changes.
  • Everybody Wants to Be Italian
    13

    Everybody Wants to Be Italian

    Jay Jablonski, Cerina Vincent, John Kapelos
    4 votes

    For Fans Of: My Big Fat Greek Wedding, Moonstruck, Chasing Liberty, Just Married, Life is Beautiful
    Why Should I Watch Everybody Wants to Be Italian: This lighthearted rom-com delivers laughs aplenty as it follows two non-Italians pretending to be part of Boston's tight-knit Italian community in order to woo each other. Delightfully quirky and boosted by hilarious misunderstandings rooted in cultural differences, this movie pays homage not only to Boston's vibrant North End but also serves as a celebration of diversity within romance. If you're looking for an offbeat comedy with plenty of amore, give this film a spin.

    Boston store owner Jake (Jay Jablonski) still loves his ex-girlfriend, Isabella (Marisa Petroro), who's now a married mom. He goes on a date with veterinarian Marisa (Cerina Vincent), during which each erroneously thinks the other is Italian. Then Isabella leaves her husband and moves in over Jake's store -- at which point he finally realizes that their relationship is over, and that he actually wants Marisa. But she's now involved with someone else... in Italy!