We all have those movies we circle back to. Some because they make us laugh. Some because they ruin us emotionally in the best way. And some because they remind us that love isn’t just candlelit dinners and slow-motion kisses—it’s messy, awkward, and sometimes deeply flawed. So here’s my very honest, no-fluff romantic movie reviews of 5 Rom-Coms That Wrecked Me—whether I liked it or not.
Before we begin, if you’re into emotional films that hit deep, check out my list of Movies That Will Emotionally Ruin You—in the Best Way. Or if you’re into lighter picks, you might like The Most Underrated Rom-Coms of the 2000s. And if you love when classic literature meets modern love stories, don’t miss Rom-Coms Inspired by Shakespeare and Other Classics, or maybe you’re into some Hidden Gems?
1. 27 Dresses (2008)
Let’s start with the classic “always a bridesmaid” trope that 27 Dresses tried to sell us as quirky and cute. This bridesmaid rom-com review wouldn’t be complete without mentioning Katherine Heigl, who plays Jane, a woman so pathologically selfless, she’s been a bridesmaid 27 times and still hasn’t caught on that she’s being walked over by literally everyone in her life.
Yes, the dress montage is iconic. Yes, James Marsden has the charm of a golden retriever in a tux. But girl. The sister betrayal? The self-sabotage? The emotional constipation?
It’s fun, fluffy, and sometimes frustrating. I like it for the sheer chaos Jane represents, but I wouldn’t recommend using this as a model for emotional maturity. Still, the wedding scenes slap.
Rating: 6.5/10—for the dresses and Marsden’s smirk.
2. First Daughter (2004)
This romantic teen movie review dives into a presidential coming-of-age fantasy wrapped in early 2000s fashion and angst. Katie Holmes plays Samantha, the president’s daughter who wants a normal college life and ends up falling for a guy who’s definitely not who he says he is.
This movie has all the ingredients of a teen rom-com but ends up somewhere between cute and mildly disappointing. It tries to give us girlhood and growth, but the execution feels like it couldn’t decide whether it wanted to be Disney Channel sweet or angsty rom-dramatic.
I rewatch it for the aesthetic. The storytelling? Mid. Katie Holmes? Adorable. Chemistry? Eh.
Rating: 5.5/10—for vibes and vibes only.
3. Bride Wars (2009)
This wedding movie review wouldn’t be fair without including the delightful mess that is Bride Wars. This friendship rom-com takes two best friends, double-books their dream wedding venue, and watches them go full bridezilla on each other. Anne Hathaway and Kate Hudson give us drama, sabotage, and enough passive aggression to fuel a suburban PTA meeting.
Here’s the thing: the premise is ridiculous. Like, can y’all just not share a weekend? But the movie leans into the absurdity and delivers a war that’s more emotional than anything else. I weirdly love it, even when I hate how immature both characters are being.
Bonus points for the “you’re not the you I remember” line that somehow hits harder than it should.
Rating: 7/10—for the chaos and catfights in Vera Wang.
If you enjoy chaotic female friendships on screen, check out my post on Top 10 Romantic Movies to Watch When You’re Sad—some are surprisingly healing.
4. Eternal Sunshine of the Spotless Mind (2004)
Whew. Let’s take a turn.
This emotional romantic movie review could be a blog of its own. This isn’t your typical rom-com. This is a film that crawls into your brain, pokes around your heartbreak, and then asks you: if you could erase your pain, would you?
Jim Carrey and Kate Winslet play Joel and Clementine—two people who fall in love, fall apart, and literally get each other erased from their memories. The storytelling is nonlinear, the visuals are haunting, and the emotions? Raw. Ugly. Real.
I don’t watch this often because it genuinely hurts to. But in the best, most meaningful way. This is love stripped of polish. It’s not about happy endings; it’s about human connection in all its broken, hopeful mess.
Rating: 9/10—only because 10/10 would erase me.
5. Jerry Maguire (1996)
This classic romantic drama review brings us to Jerry Maguire—part sports drama, part midlife crisis, and part soft romance. Tom Cruise plays Jerry, a sports agent who has a moral awakening, tanks his career, and clings to the one person who believes in him: Renée Zellweger’s sweet, single-mom character, Dorothy.
It’s hard to say if this is a love story or a story about self-discovery that happens to have love in it. The “you complete me” line is iconic, yes, but what really gets me is the “you had me at hello.” That quiet vulnerability? Chef’s kiss.
The pacing can be slow, and sometimes you want to shake Jerry out of his existential slump. But it hits different when you’re older and realize that love sometimes shows up in the mess of trying to find yourself.
Rating: 8/10—for the emotional payoff and Zellweger’s big, soft eyes.
Final Thoughts on Rom-Coms That Wrecked Me
These romantic movie reviews aren’t about perfection. Some are outdated. Some problematic. But each one gave me something—whether it was laughter, tears, or a soft ache that stayed behind like a love letter never sent.
If you’re a hopeless romantic, a curious cynic, or someone who just likes their rom-coms with a side of chaos, give these films a rewatch. Or don’t. But remember: love on-screen is never just love. It’s a mirror. And well these were the 5 5 Rom-Coms That Wrecked Me.
And sometimes? It reflects exactly what we needed to see.