Rob, a record store owner and compulsive list maker, recounts his top five breakups, including the one in progress. The film centers on Rob Gordon, a self-confessed music geek, who after getting dumped by his girlfriend, decides to look up some of his old flames to figure out what he keeps doing wrong. Rob spends his days at his record store, Championship Vinyl, where he holds court over the customers and is supported by his friends Dick and Barry. He also develops a dislike for two shoplifting skateboarder teenagers, Vince and Justin. Rob eventually tries to win back his lost girlfriend Laura while starting his own record label.
After reading an article that suggests women who have had 20 or more relationships are unlikely to ever find a husband, Ally Darling starts to panic. In order to avoid becoming number 20, she decides to track down all of her ex-boyfriends in the hopes of rekindling a romance and finding 'the one'. With the help of her neighbor Colin, she embarks on a quest to revisit her past and discover if any of her exes are worth a second chance.
Will Hayes, a political consultant, shares his love story with his daughter Maya, leaving her to guess which woman is her mother. The story follows Will's relationships with Emily, April, and Summer, revealing his journey of love and self-discovery.
A young couple navigates the ups and downs of their relationship while attending college in New York City. They face challenges such as lovesickness, a car crash, and depression, but ultimately find their way back to each other. Along the way, they encounter a group of friends, an art gallery, and a fictional reality show.
After a string of unsuccessful relationships, Lucy decides to try a new approach to dating. With the help of her friends, she embarks on a journey to find her perfect match.
A man in his thirties, who is still recovering from his recent breakup, reflects on his past relationships with his last five girlfriends. Through a series of flashbacks, he explores the ups and downs of each relationship and the lessons he learned from them. As he reminisces, he begins to see patterns and similarities in the women he has dated. With the help of his best friend, he tries to decipher the reasons behind his failed relationships and find meaning in his love life.
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