Movies that feel like Two for the Road (1967)

Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.

A deadpan young man obsessed with death meets an eccentric septuagenarian who teaches him to live life to the fullest.

New York comedian Alvy Singer falls in love with the ditsy Annie Hall.

A man and woman meet by chance at a romantic inn over dinner and, although both are happily married to others, they find themselves in the same bed the next morning questioning how this could have happened. They agree to meet on the same weekend each year—in the same hotel room—and the years pass each has some personal crisis that the other helps them through, often without both of them understanding what is going on.

Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although he often has to deal with the aftermath of their visits, one night he's left with a major problem to solve.

Brave new steps put Scott's career in jeopardy. With a new partner and determination, can he still succeed?

Overwhelmed by her suffocating schedule, touring European princess Ann takes off for a night while in Rome. When a sedative she took from her doctor kicks in, however, she falls asleep on a park bench and is found by an American reporter, Joe Bradley, who takes her back to his apartment for safety. At work the next morning, Joe finds out Ann's regal identity and bets his editor he can get exclusive interview with her, but romance soon gets in the way.

Plucky Englishwoman Joan Webster travels to the remote islands of the Scottish Hebrides in order to marry a wealthy industrialist. Trapped by inclement weather on the Isle of Mull and unable to continue to her destination, Joan finds herself charmed by the straightforward, no-nonsense islanders around her, and becomes increasingly attracted to naval officer Torquil MacNeil, who holds a secret that may change her life forever.

Average student and eternal optimist Lloyd Dobler seeks to capture the heart of Diane Court, a beautiful but unattainable valedictorian classmate. He surprises just about everyone - including himself - when she returns the sentiment. However, Diane's divorced, over-protective father soon begins to disapprove of the match, and Lloyd realises that it's going to take more than just the power of love to conquer all.

Jerry Maguire used to be a typical sports agent: willing to do just about anything he could to get the biggest possible contracts for his clients, plus a nice commission for himself. Then, one day, he suddenly has second thoughts about what he's really doing. When he voices these doubts, he ends up losing his job and all of his clients, save Rod Tidwell, an egomaniacal football player.

Raj is a rich, carefree, happy-go-lucky second generation NRI. Simran is the daughter of Chaudhary Baldev Singh, who in spite of being an NRI is very strict about adherence to Indian values. Simran has left for India to be married to her childhood fiancé. Raj leaves for India with a mission at his hands, to claim his lady love under the noses of her whole family. Thus begins a saga.

Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.