If You Like Regretting You, Watch These 5 Movies

When “based on a true story” isn’t just a gimmick
Okay, so I went into Regretting You thinking I was ready for the emotional rollercoaster, but that betrayal and the sheer level of family drama between Morgan and Clara wrecked me. You know that feeling when a story just grips you and you can’t put it down? That’s the vibe I’m chasing.
If you’re like me and need more movies with messy, deeply flawed characters, huge life-altering tragedies, and that sweet, messy struggle for a second chance, then this list is for you. Grab your favorite comfort blanket and your emergency tissues. Let’s dive into the drama!
Looking for even more picks? Don’t miss TV critic Randy Harward’s weekly What To Watch guide for the freshest streaming recs.
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1. The Notebook (2004)
I mean, we have to start here, right? This is the granddaddy of all Nicholas Sparks tearjerkers. If you loved the themes of regret, missed opportunities, and a love that is so strong it basically defies logic, The Notebook is your essential rewatch. Plus, the chemistry between Ryan Gosling and Rachel McAdams still makes my jaw drop. It’s messy, dramatic, and totally worth the crying jag.
Where to stream The Notebook
2. The Last Letter from Your Lover (2021)
I absolutely loved the interwoven timelines in this one! It’s all about a journalist who finds a trove of secret love letters from the 1960s, which reveal a passionate, forbidden affair. Much like Regretting You, this movie is built on a massive betrayal and the tragic secret that kept two people apart. It’s swoon-worthy and makes me wonder if those star-crossed lovers ever finally got their second chance.
Where to stream The Last Letter from Your Lover
3. The Best of Me (2014)
This is another deep-cut Sparks pick, perfect for fans who love it when a tragedy forces two people back together. These high school sweethearts reunite decades later for a funeral and immediately regret their past choices. It’s the ultimate “what if” story about being given an unexpected second chance to rekindle a love that never truly died. Get ready for some classic small-town intense feels.
Where to stream The Best of Me
4. Where the Crawdads Sing (2022)
Okay, this one hits the family drama and trauma button hard. It’s about a young girl named Kya, who is abandoned by everyone and must survive alone in the marsh. If you found the dynamic of Clara navigating her pain in Regretting You compelling, you’ll love Kya’s heartbreaking journey. It’s beautiful, mysterious, and all about a woman finding strength after unbelievable childhood betrayal.
Where to stream Where the Crawdads Sing
5. Blue Valentine (2010)
Warning: This one is for when you want the rawest, most realistic kind of relationship tragedy. It uses parallel timelines to show the magical start of a passionate love affair and the heartbreaking end of a marriage. There are no easy answers, just brutal honesty about regret and failure. It’s perfect if you appreciated how Regretting You didn’t shy away from how dark betrayal and marital issues can be.