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In 1985, Robbie Hart (Adam Sandler) is an engaging and entertaining wedding singer from Ridgefield, New Jersey. He is engaged to his long-time girlfriend, Linda (Angela Featherstone), who was attracted to him at a time when he dreamed of becoming a rock star. Robbie meets and befriends a waitress, Julia Sullivan (Drew Barrymore), at the reception hall where he regularly performs. Julia is also engaged, to businessman Glenn Gulia (Matthew Glave) and he promises to sing at their wedding.
On their wedding day, Robbie's sister, Kate, informs him about Linda changing her mind about the wedding, leaving Robbie emotionally devastated and humiliated. Later that day, Linda visits Robbie and he confronts her for leaving him at the altar, rather than tell him the truth so they can cancel the wedding. She reveals that she stopped loving him when she found out that he lost his ambitions of being a rock star and instead became a wedding singer. Linda tells Robbie that after talking to her friends, she realizes she can't continue lying to herself and ends their relationship. He tries to move forward with his life, but despair hinders his performances. Julia tries to cheer him up and later asks him to help her plan her own wedding. Robbie eventually agrees and their friendship blossoms. Meanwhile, as he spends more time with Julia, Robbie begins to realize how shallow Linda is. During a double date between Julia and Glenn, and Julia's cousin, Holly (Christine Taylor), Robbie learns that Glenn frequently cheats on Julia and doesn't plan to stop after being married.
Julia and Robbie are increasingly confused by their deepening feelings for each other. Robbie tells Julia he has plans to retire from singing and pursue a more conventional career, thinking that will impress Julia. She becomes angry with him for assuming that she is marrying Glenn for his money (although she is under pressure from her worried parents to do just that so she will not tread water as they have). Dismayed, Robbie goes to a bar where his friend Sammy (Allen Covert) says that guys who refuse to settle down get forgotten, using the example of once-popular TV shows featuring single swinging guys that got cancelled due to the same old schtick, which inspires Robbie to proceed to the Sullivan house to tell Julia how he feels. When he arrives, he sees her through her bedroom window. She is wearing her wedding dress, to which Robbie mistakenly concludes that she is looking forward to marrying Glenn. In actuality, she is expressing doubts about Glenn, particularly her new name of "Julia Gulia", and thinks herself as Robbie's bride would be nice, hence her imagined glee.
Heartbroken, Robbie leaves to get drunk and finds Glenn in the midst of his "pre-bachelor party party". After a heated exchange, Glenn punches Robbie and proceeds to mock him. An intoxicated Robbie goes home and finds Linda waiting for him and wanting to reconcile. Robbie passes out, but the following morning, Linda answers the door and introduces herself as Robbie's fiancée to a crestfallen Julia. Julia runs to Glenn, wanting to be married immediately. Glenn happily offers to take her to Las Vegas. Before getting on the plane and during the flight, Julia begins to show regret for planning to marry Glenn.
Robbie awakens and, after shaking off his hangover from the previous night, tells Linda that it's over and kicks her out. Then Robbie attends the 50th wedding anniversary party of his friend Rosie (to whom he has been giving singing lessons). Inspired by this and with Rosie's encouragement, he decides to pursue Julia. Just then, Holly arrives and asks Robbie if he is still with Linda. He reveals he ended it with Linda and learns of Julia's plans to marry Glenn. Robbie, Sammy and Holly rush to the airport, where Robbie books a flight to Las Vegas. He gets a first class ticket because all coach seats are sold out. After telling his story to an empathetic audience in first class, which includes Billy Idol (playing himself, sporting his '80s trademark spiked hairdo and biker attire), Robbie learns that Glenn and Julia are on the same flight as he peeps through the curtain separating first class and coach. Over the loudspeaker and with the help of Idol and the flight crew, Robbie sings a song he has written called "Grow Old With You," which he has dedicated to Julia. When he enters the coach area, Glenn tries to attack him, only for his path to be blocked by a male flight attendant and Idol both pushing refreshment carts. When Glenn threatens Idol, a burly Idol fan also wearing biker attire forces Glenn down the aisle and a female flight attendant he tried seducing earlier pushes him into the cabin bathroom. Robbie and Julia admit their love for each other and after Idol briefly interrupts them to offer Robbie support in fulfilling his dream of being a songwriter, they share a kiss. The film ends as the scene fades to a similar kiss, this time at their wedding.