Date Night

Top 5 Rom-Coms For Date Night, All Starring Patrick Dempsey

Patrick Dempsey is a rom-com genre all by himself.

Bridget Jones Baby

A few special ingredients come together to make a good romantic comedy movie. Sure, they're predictable sometimes, but that comfort can add to the magic. A good rom-com perfectly blends a comedy wrapped around a feel-good story. These movies follow familiar formats, and that’s the way we like it. And one key indicator of a good rom-com is a charismatic leading actor. This is why, in some ways, Patrick Dempsey is the official rom-com actor.

Dempsey has been an actor since the early '80s, and he's had a long working career partly because he's got everything that makes a leading rom-com guy a winner. He's a great dresser, charming, and doesn't take himself too seriously. He's got that look in his eye that screams, "I love you," but it can also make you roll your eyes with a line that is just a little too cheesy.

Dempsey is perfect for the rom-com genre, whether he's Prince Charming, Dr. McDreamy, fiancé Andrew, or a super cheesy nerd named Ronald. And in his more than two-decades-long career, he's starred in many rom-com movies, but they're not all the same.

Here's our list of the best rom-com movies starring Patrick Dempsey.

5. Made of Honor (2008)


We love a movie with an exciting twist, and that's what Made of Honor gives us. The film follows the typical format of a romantic comedy where someone is about to choose a path in their romantic life, an underdog the viewer can't help but root for, and an interesting angle for how it all plays out. Dempsey is able to find the balance needed for the viewer to root for him, even when he’s kind of in the wrong.

Watch on Netflix here.

4. Bridget Jones's Baby (2016)

Universal Pictures

It's not easy to join a movie franchise when it's already been established, but Dempsey fit right into Bridget Jones's world. In the final movie in a trilogy, Dempsey went head-to-head with fellow rom-com standout Colin Firth. Dempsey could fill the void of Hugh Grant missing without leaving the viewer feeling like something was missing. Not an easy feat.

Watch on Netflix here.

3. Loverboy (1989)

TriStar Pictures

Loverboy is a typical late-80s movie with a character who's a mix of nerdy and unassuming. In this movie, Dempsey plays Randy, an unfocused college grad who doesn't know what he wants to do with his life. He's bumbling but charming, and through the movie, he finds himself in a situation with older ladies who find his charm irresistible — their own marriages be damned.

Rent or buy on Amazon Prime.

2. Sweet Home Alabama (2002)

Touchstone Pictures

The early aughts were a perfect time for rom-coms, and Dempsey was made for this time in movies. Sweet Home Alabama features other genre-heavy hitters like Reese Witherspoon and Josh Lucas, who, together with Dempsey, made this a much-loved romantic film. Dempsey was able to show some versatility with this role since he's not necessarily the character we're supposed to root for. He does just as good of a job here as in his other roles.

Watch on Disney+ here.

1. Enchanted (2007)


Enchanted is a really charming movie because it allows adults to relive some of their favorite kid stories but with an interesting, more grown-up twist. Dempsey feels like he was literally made for this role as Prince Charming in the real world. He adds the perfect mix of aloof and charming, making us want to see how this storyline plays out. And the good news is we get to see how it plays out; Dempsey reprises his role of Prince Charming in Disenchanted, out now.

Watch on Disney+ here.