5 K-Dramas where a second chance at love hurts the most: Lovestruck in the City to Uncontrollably Fond

You know it, Lovestruck fans. You won't forget Ji Chang-wook's tearful, broken speech in the restaurant. You remember how he says, "Why does it hurt that you're happy?"

Sigh. You would think the second chance at love dramas would be somewhat easy. But K-Dramas have turned that mood around. It hurts. So, here's our roundup of the series that show you the second chance...but not without some pain.

A slow-burning, emotionally charged story, Lovestruck in the City, starring Kim Ji-won and Ji Chang-wook, follows a woman who escapes a life of drudgery and betrayal for the summer of a lifetime. But it’s not what it seems at first: adopting a new identity and persona, she says yes to life and begins a romance with another man — only to vanish from his life completely. Heartbroken and lost, he searches for her, only to discover she isn’t the person he thought she was. Fate, however, gives them a second chance — not just at love, but at understanding themselves.

Who has signed up for some heartbreak? Starring Kim Woo-bin and Bae Suzy, the drama follows two former lovers who reunite years later — he’s now a top actor hiding a life-changing secret, and she’s a jaded documentary producer who wants nothing to do with him. Their second chance at love feels raw, messy, and achingly beautiful as old wounds resurface and the truth they’ve both buried comes crashing back. Bring tissues. Lots of them.

If you love a good 'we almost had something… now what?' kind of second-chance romance, this stylish Netflix drama delivers. Starring Chae Soo-bin and Choi Min-ho, the story follows best friends Ji-eun and Ji-woo, who once tried dating but broke up before things could get serious. Years later, while working in the chaotic Seoul fashion world, the two keep orbiting each other — torn between staying just friends and confronting the feelings they left unresolved. Their will-they/won’t-they tension is soft, slow, and quietly emotional, wrapped in high fashion, friendship, and a very real second chance at something deeper.

This isn’t your regular love story — and it’s definitely not the healing, cosy kind. Starring Yoo Yeon-seok and Moon Ga-young, the drama is a raw, unfiltered look at how love can twist when fear, insecurity, and unresolved wounds take the wheel. Two people who are attracted to each other, find reasons to stay apart, only to find themselves pulled back into a painful, magnetic second chance neither is truly ready for. It’s brilliant, complex, and brutally honest about how we sabotage the very relationships we crave. Watch it — but be emotionally armed.

A stunning blend of past lives and present-day fate, Chicago Typewriter stars Yoo Ah-in, Im Soo-jung, and Go Kyung-pyo in a story where a love cut short in the 1930s gets a second chance nearly a century later. A famous but tormented writer, a devoted fan with a mysterious past, and a ghostly best friend find their lives intertwined by a vintage typewriter that links them to their former selves — freedom fighters during the Japanese occupation.

As memories resurface, so does an unfinished love story filled with guilt, sacrifice, and destiny. It’s atmospheric, emotional, and deeply romantic — a second chance not just at love, but at healing a tragedy that never found closure the first time around.