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Without aging myself, let’s just say I’ve seen a lot of rom-coms over the last several decades. I’ve seen some of the best rom-coms, some of the most memorable and some of the silliest. I’ve also seen some of the most mediocre and some romances that might be better than you remember. But, there are some rom-coms that are so memorably bad they deserve to be on a list of the worst of the worst, and I’ve spelled out some big stinkers here.
To be clear, I’ve seen enough rom-coms with my Amazon Prime subscription to know there are myriad examples of OK rom-coms made on a shoestring budget for alternative distribution pathways. When compiling this list I didn’t save any room for some of Hallmark’s films (though some of those are delightful) or some of the lower budget stuff that I’ve caught on streaming before.
The movies you’ll find here are all pretty notable in terms of budget, cast and distribution methods. I asked myself two questions before adding: First, was it a low budget rom-com with mediocre expectations, or was a studio stacking up solid talent? Second, what qualifies the movie as bad? Was it script, unromantic leads, or something else? There are myriad reasons a movie can suck, and these run the gamut.
Shallow Hal With Jack Black And Gwyneth Paltrow (2001)
Shallow Hal was a moderately reviewed Farrelly Brothers vehicle when it came out in 2001. The movie’s about a man who is hypnotized into believing his overweight girlfriend is, well, Gwyneth Paltrow. Roger Ebert wrote at the time the jokes are “tilted toward empathy,” but the rom-com hasn’t held up like their other popular rom-com vehicle There’s Something About Mary has. In fact, it feels pretty icky. It doesn’t help that Jack Black’s great Christmas film The Holiday is far superior, either.
Home Fries With Drew Barrymore And Luke Wilson (1998)
It’s been a minute, but if I’m remembering correctly this one starts with an affair Drew Barrymore‘s character is involved in. The man she’s affairin’ with dies and then she becomes intimately connected to another man (Wilson) who was actually implicated in his death. Forget the zany plot, though; I mostly remember Drew Barrymore, who has the most late nineties haircut on record. I’m glad that phase in fashion is over, and I’m equally glad this movie has faded in memory over the years.
Gigli With Ben Affleck And Jennifer Lopez (2003)
Gigli has kind of become the laughingstock of the entire romantic comedy genre, and it’s not without good reason. The Ben Affleck and Jennifer Lopez vehicle was panned when it came out in 2003, and I’d be willing to believe more people have the opinion it’s a bad film than have actually seen the movie, though Affleck maintains the media circus caused the poor reviews.
To be honest with you, it’s probably been 20 years since I’ve seen Gigli, and this entry is predicated on the fact that I disliked it so much the first time around I couldn’t bring myself to watch it again. It’s not that Affleck and JLo didn’t have chemistry, obviously, but the movie’s just strange and difficult to watch.
Made Of Honor With Patrick Dempsey And Michelle Monaghan (2008)
Sexiest Man Alive Patrick Dempsey has made some good rom-coms in his day, but Made of Honor is not one of them. The plot of this movie has Dempsey taking over Maid of Honor duties for the woman he is actually in love with’s wedding, and dealing with his ex girlfriend getting upset she’s no longer the maid of honor.
He spends the rest of the movie trying to woo the bride while she’s planning her wedding, and the plot’s so mean-spirited it ends –and sorry about this spoiler — with our hero getting punched in the face. Because he’s the worst and he absolutely deserves it. Skip this one and pick up Enchanted instead.
Grease 2 With Michelle Pfeiffer And Maxwell Caulfield (1982)
Listen, I know some of you may be Grease 2 apologists, but the sequel to the hit classic Grease is simply bad. Not only was the rehash of the OG film a critical failure, it also flopped at the box office when it was released in 1982, and it’s so memorably terrible that Michelle Pfeiffer still gets asked about Grease 2 on a semi-regular basis. She’ll defend the movie. I won’t.
Down To You With Freddie Prinze Jr. And Julia Styles (2000)
There was a period of time where Freddie Prinze Jr. and Julia Styles were all over the romance genre. He starred in She’s All That and Summer Catch. She starred in the iconic 10 Things I Hate About You and Save The Last Dance. But in between those movies came Down To You, a rom-com we probably all would have forgotten about had it not nabbed the distinction of being the lowest rated rom-com on Rotten Tomatoes at 3%. There’s just no chemistry and little plot, and while the movie ends on a hopeful note, it’s a slog to get there.
He’s All That With Addison Rae And Tanner Buchanan (2021)
Speaking of Freddie Prinze Jr., the actor’s cute-yet-silly She’s All That romance got a reimagining with He’s All That on Netflix in 2021. It’s not a great successor to a rom-com that’s fondly remembered, to put it lightly. It’s more cheaply made than you would expect for a heavily buzzed about sequel with some big names. Though it stars a Cobra Kai favorite in Buchanan, he’s less fun to watch in this format, and he’s working opposite a TikTok star who’s not an actress at all. This could have been great. It wasn’t.
This Means War With Tom Hardy, Chris Pine And Reese Witherspoon (2012)
McG certainly knows how to blow things up in This Means War, and I’m talking the plot, not the action sequences. While I sometimes love the director’s bent — I think the first episode of Fox’s Lethal Weapon reboot does the McG thing solidly — I’m not sure what prompted him to tackle a rom-com. I also don’t know how A-listers like Reese Witherspoon, Chris Pine and, yes, Tom Hardy, were convinced to say yes to this CIA-based romance. Maybe because it merges two genres together? It just doesn’t work.
Paternity With Burt Reynolds And Beverly D’Angelo (1981)
Burt Reynolds had a long and storied career but he still made some doozies in the rom-com genre, Paternity included. While the idea that in the eighties a movie about how a man might want to have a kid on his own without relying on a partner is sort of forward-thinking, the plot here is shenanigans. The premise of a man looking for a surrogate makes for an awkward meet-cute, and then Reynolds’ character, Buddy, isn’t even particularly nice to D’Angelo’s Maggie before the inevitable conclusion. Yet the actor would later defend the role, calling it “not a terrible film.” High praise.
Something Borrowed With Kate Hudson, John Krasinski And Ginnifer Goodwin (2011)
There’s probably no entry on this list that earns more vitriol from me personally than Something Borrowed, which might seem weird, because the movie is well-acted and actually has an OK script. Normally a movie like this would simply fade into the background of most rom-com lists, but this one is so hate-able. The characters are awful people and because it’s a big cheating fest, there’s literally no one to root for. I probably would have liked this movie if everyone got their comeuppance in the end, but they don’t. As they say on reddit, “everyone sucks here.”
In The Mix With Usher And Emmanuelle Chriqui (2005)
Remember that time the world tried to make Usher an a-list actor? You don’t? It’s probably better that way, because In The Mix is awful. First and foremost, it’s hammy plot revolves around a mobster asking a DJ to keep an eye on his daughter. Usher’s fine in small roles in She’s All That and Popstar: Never Stop Never Stopping, but there’s a reason In The Mix is one of the lowest-rated rom-coms on IMDB and I’d argue it’s because he got, he got it bad(ly) done.
Your Place Or Mine With Reese Witherspoon And Ashton Kutcher (2023)
There’s a chance that Your Place or Mine will go down in the annals of rom-com history as a solid OK, but here’s why I think it’s among the worst: Reese Witherspoon and Ashton Kutcher literally have no chemistry. None. Zero. Zilch. It’s not because either of them are bad at filming rom-coms, either. In fact, Reese is responsible for Sweet Home Alabama and a laundry list of delightful films in this genre. Ashton Kutcher ain’t half bad in No Strings Attached. Together, however, there’s no movie magic.
Wild Mountain Thyme With Jamie Dornan And Emily Blunt (2020)
Listen, a lot of weird content came out around the pandemic, but this is a rare miss for both Dornan and Blunt, and given there were way fewer releases in this period, more people heard of and watched this movie than might have otherwise. It’s hard to even describe Wild Mountain Thyme, but I guess if I had to I’d call it a strange indie rom-com, and not strange in a fun or amusing way, just odd. I don’t want to spoil you on Wild Mountain Thyme‘s wild ending, as it’s the most notable part of the movie and may be worth watching just to know. Still, I can’t in good conscience recommend this movie.
Good Luck Chuck With Dane Cook And Jessica Alba (2007)
Another rom-com with a historically low Rotten Tomatoes rating of 5%, Good Luck Chuck stars Dane Cook and Jessica Alba, who were at the time pretty huge names. This one’s about a literal hex placed on a dude that says after he hooks up with a woman, she’ll marry the next guy she’s with, which is not a problem, until he falls for a girl named Cam. Lots of yuck in this, and even the pic from this movie I added to this post makes me hate it. So unfunny.
Listen, there are a lot more crappy rom-coms that could have made this list, but these are some of the ones that really wear me (and some other members of the CinemaBlend staff) down hard. Now the rom-com genre is making a comeback from its mid-aughts lows, I can’t wait to talk about more of these down the line. No, really.
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