Only Lonely (2017)

Oliver Hobbs was okay with dying alone...until he actually did die alone, in 2055, at the age of 60. Instead of moving on to the next life, Oliver woke up in his 21-year-old body on the worst night of his life: the night of the party where he lost his dream girl, Alicia, to another man. Figuring this is the universe's way of telling him he screwed up, big-time, Oliver spends the night trying to win Alicia over. However, Oliver has always been an odd duck, and his ability to talk to women hasn't improved in his second life. Meanwhile, his romantic adversary, Bobby Wallis (AKA Alicia's future husband), thwarts Oliver at every turn, and a DJ who just happens to go by "Reaper" tails Oliver all night, dispensing little gems of wisdom while also maybe-possibly being an agent of death.