My Dear Desperado

When a young woman named Se-jin moves to Seoul for a fresh start, she finds herself living next door to a middle-aged gangster named Dong-chul. Despite their vastly different lifestyles, they form a tentative friendship after Dong-chul helps Se-jin out a couple of times. One night, Se-jin, feeling defeated by her job search, ends up drinking with Dong-chul and having a one-night stand with him. To save face with her father, Se-jin asks Dong-chul to pose as her wealthy boyfriend during a visit home, but things don't go as planned. Meanwhile, Dong-chul is caught up in a gang war and must navigate a dangerous apology to a group of hapkido athletes. Will Se-jin and Dong-chul's unlikely friendship survive the challenges they face?

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Some movies that have similar genres and were produced around the same time as My Dear Desperado include The Sisterhood of the Traveling Pants, The Oranges, Love & Other Drugs, Daddy's Little Girls, He's Just Not That Into You, The Switch.