Many couples have to go through the harrowing journey of finding a movie that both of them will enjoy, and still fits the feeling of a date night. 

Fortunately, there are such films.

The first example is, A League of Their Own (1992), directed by Penny Marshall, and starring Geena Davis, Lori Petty, and Tom Hanks.

The film is based around a real life story. During World War II, many young men were sent off to war, leading to shortage of baseball players. This led to the formation of a women’s baseball league.

The story follows sisters Dottie (Geena Davis) and Kit (Lori Petty) being recruited as players for one of the women’s teams. The team isn’t well respected by the public at large, because they’re women playing baseball and that’s most unorthodox. 

To make it worse, their team manager is an ex-pro player, who’s now a drunk with a bad knee and an even worse attitude, named Jimmy Dugan (Tom Hanks). 

The film tackles serious subject matter like war and sexism, but despite that it’s still pretty funny. It’s humor is rapid fire – if one joke doesn’t land, chances are another joke shortly coming up will.

A good example of this in action is Ernie Capadino (Jon Lovits), the talent scout. He’s always giving off some rude but entertaining remarks that get a laugh out of the audience.

Another example is Mae and Doris (played by Madonna and Rosie O’Donnell respectively). The two actresses have great chemistry and work well off each other. 

The two are the “Odd Couple” routine, Mae is more free spirited of the two, going on dates with random guys in almost every town the team visits. While Doris is more in your face and confrontational, always saying what’s on her mind.

Tom Hanks surprised me in this film. For the first half of the film he’s pretty unlikeable, and even after cleaning his act, he’s still kind of a jerk. But he has moments where it’s shown he cares for his players, and will go to bat for them (no pun intended). At the very least, it’s shown that when he’s not on the booze, he still has what it takes to be a good manager.

The main characters, Dottie and Kit, are well acted but are the least interesting characters in the cast. While the rest of the cast brings enough charisma and panache to really make them stand out as characters, Dottie and Kit have a harder time standing out due to their less outlandish personalities.

Their character arcs, while down to earth and realistic, can get kind of annoying. Their plot revolves around Dottie being the best player around and star player, and Kit is jealous and feels like she’s in her sister’s shadow. It’s good drama, and is well written and acted, but it brings the film to a halt.

Another problem the film has is that it focuses on too many characters to make them stand out, and some characters that are important at the beginning either fade into the background or just disappear.

A League of Their Own is a fun watch and can be hilarious, despite its more serious subject matter. But it’s because of that serious subject matter that I’d suggest watching it as a date film later on in a relationship.

The next film that’d make a good date movie is 10 Things I Hate About You (1999) directed by Gil Junger. The movie is a modern adaptation of the Shakespeare play The Taming of the Shrew.

New transfer student Cameron James (played by a young Joseph Gordon-Levitt) falls head over heels for a girl named Bianca Stratford (Larisa Oleynik). 

Unfortunately, she can’t date until her older sister, Kat (Juila Stiles), starts dating. And Kat is in no hurry to start dating, and is hostile and confrontational to most boys, causing most to be intimidated by her. So Cameron, along with his new friend Michael (David Krumholtz), manipulate events to have the baddest boy in their school, Patrick Verona (played by the late Heath Ledger), to date Kat, so Cameron can date Bianca. 

The film is so late ‘90s, it couldn’t be mistaken for any other period of time if it tried. Despite that, the dialogue and characters have aged remarkably well.

The high school characters, while way more successful than I or anyone else I knew in high school, still feel like high schoolers. They make stupid decisions, flip flop between emotions, don’t fully plan things out, and make rash decisions.

The adults aren’t much more mature. The principal, Ms. Perky (Allison Janney),  is not so subtly writing smut, and curses in front of students like it’s nothing. But by far my favorite character is the English teacher, Mr. Morgan (Daryl Mitchell), who takes crap from no one, has a short fuse, and has some of the best lines in the film.

Thankfully, most of the romance between the cast works in this romance-comedy. Ledger and Stiles have good romantic chemistry. Even if the film contains most of the tropes of a romance story, it’s well executed. 

That being said it stumbles a bit near the end. They use the old romance plot point where there’s a misconception and it looks like the two romantic leads won’t end up together, even though everyone in the audience knows they will.

10 Things I Hate About You is one of those films that are very dated, yet has a very timeless story that feels suitable for today, and works great as a first date flick. 

The last film I’m talking about is an absolute classic, The Princess Bride (1987) directed by Rob Reiner. The film itself is based on a 1973 novel of the same name written by William Goldman.

The film is about a grandfather (Peter Falk) reading a book to his grandson (Fred Savage) that he used to read to the grandson’s father.

The story within the story is about Princess Buttercup (Robin Wright), a peasant girl who lost her boy toy Westley (Cary Elwes) when he was killed by the Dread Pirate Roberts, and vows to never love again. 

She is later married to Prince Humperdink (Chris Sarandon) and while she’s horseback riding is kidnapped by three thugs, Vizzini (Wallace Shawn), the brains, Inigo Montoya (Mandy Patinkin), the swordsman, and Fezzik (Andre the Giant), the muscle.

After that is a story filled with as the film says,  “Fencing, fighting, torture, revenge, giants, monsters, chases, escapes, true love, and miracles.”

The film is fondly remembered for a reason, it’s just that funny. Almost throughout the entire film people having casual conversations while fighting to the death.

Even if what’s happening is completely out of this world, like R.O.U.S’s (rodents of unusual size) or people literally coming back from the dead, everyone acts like it’s just another Tuesday. Prince Humperdink plans to start a war with a neighboring country, and that’s a side plot. 

It also helps that the movie is just so quotable. Who can forget the words Inigo plans to say to his father’s killer, how Vizzini keeps on using the word “inconceivable” incorrectly, or how Miracle Max (Billy Crystal) explains how someone is only “mostly dead.” 

Speaking of Vizzini, Wallace Shawn steals whole scenes whenever he’s on screen. He’s the best part of the film.

Despite all this praise of the story featured in the film, the framing device is still pretty funny, with the grandson getting more and more invested and the grandpa getting in some good quips as the story goes. 

The Princess Bride, is a film that not only works a good date night film regardless of how far a person is in a relationship, but also is just a film everyone should watch at least once.

Patrick will soon be featured in his own rom-com, Ten Things I Write About You.