20 best movies like The Sure Thing (1985)

Eddy and Stuart share two-thirds of a dormitory suite. Due to bureaucratic error, a woman named Alex is added to their room. At first, relations among the three are tense. Soon, however, Alex falls for Eddy, and Stuart lusts after Alex.

When an overachieving high school student decides to travel around the country to choose the perfect college, her overprotective cop father also decides to accompany her in order to keep her on the straight and narrow.

A budding romance between noble underachiever Lloyd Dobler and high school valedictorian Diane Court is threatened when Diane's overly possessive, disapproving father interferes with their relationship. With a prized scholarship to study abroad hanging in the balance, Diane must find a way to make both men happy.

Matt falls for Casey, the new girl in school. She's fun-loving and eccentric, but there's a darkness to her whimsy that Matt can't begin to comprehend. When Casey attempts to commit suicide, her parents place her in a mental institution. Matt springs her out, and together the young lovers head on a road trip. They believe their love can "cure" Casey's problems. Matt starts to wonder, though, if are they inspired or misguided.

Teenager Jones has opted not to go to college and is instead renting a room in a boarding house to work on his writing skills. Soon, Jones finds himself dividing his time between two women: a young actress named Lisa and a photographer named Jane. After Jane's ex-boyfriend arrives to help her recover from a car accident, Jones begins to understand just how much he cares for her.

Two students at neighboring colleges get swept up in first love. Pookie Adams, a kooky misfit with no family or friends, clings to the quiet and studious Jerry, who has the ability to make a choice of living in Pookie's private world or be accepted by the society that Pookie rejects. Unwittingly, it is through their awkward relationship that Pookie prepares Jerry for the world of "weirdos" that she doesn't fit into.

In this coming-of-age comedy, Tim Dunphy is leading a go-nowhere existence, spending his days smoking pot and hanging out with his best friend, Drugs Delaney. But Tim's lazy days of getting high are jettisoned after a brush with the law convinces his blue-collar dad to send him to a Connecticut prep school. The one saving grace of the new school is Jane, a fellow student Tim falls for immediately.

Three teenage girls come of age while working at a pizza parlor in Mystic Connecticut.

An American girl on vacation in Italy finds an unanswered "letter to Juliet" -- one of thousands of missives left at the fictional lover's Verona courtyard, which are typically answered by a the "secretaries of Juliet" -- and she goes on a quest to find the lovers referenced in the letter.

A young man goes on a road trip with an old lady he saves from a hospital.

Set on an island off the coast of New England in the summer of 1965, Moonrise Kingdom tells the story of two twelve-year-olds who fall in love, make a secret pact, and run away together into the wilderness. As various authorities try to hunt them down, a violent storm is brewing off-shore – and the peaceful island community is turned upside down in more ways than anyone can handle.

A clinically depressed teenager gets a new start after he checks himself into an adult psychiatric ward.

David Portnoy, a 15-year-old birding fanatic, thinks that he's made the discovery of a lifetime. So, on the eve of his father's remarriage, he escapes on an epic road trip with his best friends to solidify their place in birding history.

A hard-partying high school senior's philosophy on life changes when he meets the not-so-typical "nice girl."

While on Christmas break, college student Michael journeys to Quebec City to spend time with his attractive girlfriend, Gabriella. Not long after he arrives, Gabriella breaks up with him, but her two equally gorgeous sisters waste no time showing romantic interest. In the meantime, Michael is left to deal with Gabriella's eccentric grandmother and offbeat father, an academic who spends most of his time naked.

A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.

Stillman, a heartbroken physics student, builds a time machine when his girlfriend breaks up with him. Going back in time, he attempts to save their relationship by fixing every mistake he made—while dragging his best friend along in the process.

The film follows Grace, a young woman whose irresponsible mother blows her college fund on her younger sister's beauty pageant campaign.

Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.

Harry Sanborn is an aged music industry exec with a fondness for younger women like Marin, his latest trophy girlfriend. Things get a little awkward when Harry suffers a heart attack at the home of Marin's mother, Erica. Left in the care of Erica and his doctor, a love triangle starts to take shape.

Dorian realizes he is gay in his final year of high school. He meets another gay youth locally, but remains confused. He starts therapy, then resorts to confession in the Church, and finally comes out to his brother. Dorian then decides to come out to his father; he gets kicked out of the house.

Maggie is an uptight, single mother and college writing teacher from New York City. In an effort to reconnect with her troubled teen daughter Summer, she decides to embark on a journey to a Tuscan village where she frequented in her younger days. Upon arrival, Maggie runs into Luca a handsome former lover who is still a bachelor and lives with his eighty-year-old mother Carmen. Summer (missing her “bad boy” boyfriend in NYC) and Carmen (secretly planning a wedding against Luca’s wishes to MARCELINO, her one true love in Rome) impulsively steal Luca’s car and race off to Rome. Maggie and Luca quickly pursue allowing the two mismatched couples to spend some time together and develop a new understanding of each other.

A chain reaction of confrontations and romantic encounters occurs when college friends reunite for one's wedding.

After a distastrous first date for caterer Holly and network sports director Messer, all they have is common is a dislike for each other and their love for their goddaughter Sophie. But when they suddenly become all Sophie has in this world, Holly and Messer must set their differences aside. Juggling careers and social calendars, they'll have to find common ground while living under the same roof.

When new kid in town Ed Wallis is given an assignment to interview an older person, he turns to his mysterious neighbor, Ashby Holt for help. That new connection leads to unexpected journeys for both of them, as Ashby – who turns out to be a retired CIA assassin – deals with a terminal prognosis, and Ed deals with adjusting to life with his newly single mom and developing relationship with a brainy classmate, Eloise.

Henry and Nicky are small town pals from blue collar families with only a short time before they ship off to World War II. Henry begins romancing new-to-town Caddie Winger, believing her to be wealthy. Mischievious and irresponsible, Nicky gets into trouble which forces the other two to become involved, testing their relationship, as well as the friendship between the boys.

A sex therapist goes through puberty after the successful removal of a benign tumor resting against his pituitary gland. He experiences all the changes and effects of puberty over a three-week period.

When Elliot, a brash 23-year-old living carefree in New York City, meets the sensible Mia and receives a damning diagnosis all in the same week, his world is turned completely upside down. But as their love blossoms amidst the chaos of his treatment, they discover that Elliot's illness is not the real test of their relationship – it's everything else.

Danny Stein, a high school senior at the bottom of the social food chain, needs a prom date. As a cause of anxiety for Danny, Bart Beeber, the nerdiest guy in school, has already found a date. At the same time, Danny's divorced parents are both looking for relationships again.

An acclaimed writer, his ex-wife, and their teenaged children come to terms with the complexities of love in all its forms over the course of one tumultuous year.

This is the story of a dysfunctional New York family, and their attempts to reconcile

Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate paths for their first year of college and the summer beyond, but remain in touch by sharing their experiences with each other.

Leelee Sobieski is brash, abrasive and vulnerable as a teenage child of divorce who hides her pain behind a mask of hard-edged gothic rebellion. Albert Brooks plays a man who is her total opposite, a precise and well-ordered menswear store owner of forty-nine who manages limited expectations and protects lonely secrets with pleasant ritual and quiet, ironic reserve. These two total opposites collide in conflict then come together in a surprising alliance, changing each other's lives forever.

Two Navy men are ordered to bring a young offender to prison, but decide to show him one last good time along the way.

When her husband abruptly ends their marriage, empty nester Kate embarks on a solo second honeymoon in Africa, finding purpose and potential romance.

Ex-football star Mike Gambril meets Terry McKay on a flight to Sydney, which is forced to land on a small atoll. They become romantic on board a ship sent to take them to a larger island. They agree to meet in New York three months later to see if the attraction is real. One shows up but the other doesn't. However, a chance meeting brings them together again.

Music From Another Room is a romantic comedy that follows the exploits of Danny, a young man who grew up believing he was destined to marry the girl he helped deliver as a five year old boy when his neighbor went into emergency labor. Twenty-five years later, Danny returns to his hometown and finds the irresistible Anna Swann but she finds it easy to resist him since she is already engaged to dreamboat Eric, a very practical match. In pursuit of Anna, Danny finds himself entangled with each of the eccentric Swanns including blind, sheltered Nina, cynical sister Karen, big brother Bill and dramatic mother Grace as he fights to prove that fate should never be messed with and passion should never be practical.

When Juli meets Bryce in the second grade, she knows it's true love. After spending six years trying to convince Bryce the same, she's ready to give up - until he starts to reconsider.

Jake and Kristy Briggs are newlyweds. Being young, they are perhaps a bit unprepared for the full reality of marriage and all that it (and their parents) expect from them. Do they want babies? Their parents certainly want them to. Is married life all that there is? Things certainly aren't helped by Jake's friend Davis, who always seems to turn up just in time to put a spanner in the works.

Peggy Sue faints at a high school reunion. When she wakes up she finds herself in her own past, just before she finished school.

30 years after the first film, Oscar and Felix embark on a road trip together, to attend the wedding of Oscar's son to Felix's daughter.

During a snowy winter in the small fictional town of Knight's Ridge, Massachusetts, a group of lifelong buddies hang out, drink and struggle to connect with the women who affect their decisions, dreams and desires.

A mother takes her two sons on an unusual road trip from New York. Pittsburgh, St. Louis and eventually Hollywood in her quest to find a man to take care of them all.

Rose Morgan, who still lives with her mother, is a professor of Romantic Literature who desperately longs for passion in her life. Gregory Larkin, a mathematics professor, has been burned by passionate relationships and longs for a sexless union based on friendship and respect.

Based on a true story, the film is set in the summer of 1984 – when Margaret Thatcher is in power and the National Union of Mineworkers (NUM) is on strike. At the Gay Pride March in London, a group of gay and lesbian activists decides to raise money to support the families of the striking miners. But there is a problem - the union seems embarrassed to receive their support. However the activists are not deterred. They decide to ignore the union and go direct to the miners. They identify a mining village of Onllwyn, in the Dulais Valley in Wales, and later set off in a mini bus to make their donation in person. And so begins the extraordinary story of two seemingly alien communities who form a surprising and ultimately triumphant partnership.

Elizabeth is a charming anchorwoman who seeks advice from her dog's therapist. Tara is a spunky barista who dreams of a life beyond the coffee shop. Daisy is a dog walker who's enamored with a client. Garrett pines for a woman while trying to keep his adopt-a-dog business afloat. The beloved canines in their lives soon start to influence their careers, friendships and romantic relationships in funny and unexpected ways.

Mona Gray is a 20-year-old loner who, as a child, turned to math for salvation after her father became ill. As an adult, Mona now teaches the subject and must help her students through their own crises.

After spending two decades in England, Bill Bryson returns to the U.S., where he decides the best way to connect with his homeland is to hike the Appalachian Trail with one of his oldest friends.

Alex Whitman (Matthew Perry) is a designer from New York City who is sent to Las Vegas to supervise the construction of a nightclub that his firm has been hired to build. Alex is a straight-laced WASP-ish type who, while enjoying a night on the town, meets Isabel Fuentes (Salma Hayek), a free-spirited Mexican-American photographer. Alex and Isabel are overtaken by lust at first sight and end up sp

On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to ... lovers?