THE PRINCESS BRIDE (1987)

Let’s kick things off right…The Princess Bride is director Rob Reiner’s adaptation of William Goldman’s book of the same name. Don’t be fooled by its name, though, because this dangerous fairy tale is more in the vein of The NeverEnding Story than The Notebook. It’s filled with fantastical adventure and surprises, only as it can deliver, by way of its unique narrative structure. This cult classic (with quotable lines galore) will allow you to experience piracy, murder, revenge, beast-fighting, torture, poison, humor, games of wit, and true love. The star-studded cast helps things along, with the likes of Cary Elwes, Robin Wright, Billy Crystal, and Andre the Giant to name a few. If your loved one should ever ask to watch this film, the proper response is, “as you wish”.

SAY ANYTHING (1989)

Written and directed by Cameron Crowe, Say Anything is more than just an angsty, teen love story. It is also about being authentically oneself and following your heart, no matter what society’s expectations are. John Cusack plays his part perfectly, and we love him for it. John Mahoney plays the hypocritical father that just wants the best for his daughter, played by Ione Skye. Plus, there are important life lessons to be found, like if you ever have a fight with your significant other, standing outside of his or her window with your arms lifted high and playing beautiful music (boombox not required) is a guaranteed way to get out of whatever trouble you are in.

GROUNDHOG DAY (1993)

Groundhog Day finds Bill Murray doing what he does best, playing an over-the-top, cocky narcissist, and delivering on his special comedic formula for success. He is caught in a never-ending time loop, forced to live the same day repeatedly. He tries to use this “curse” as a hack to win over the lovely Andie MacDowell’s character, but it isn’t until he stops “trying” that he is able to finally succeed. His journey reflects our own in so many ways, providing a useful framework for being a good person simply because it’s the right thing to do. If we can attack life from that perspective more often than not, you are probably going to win the girl anyways.

JERRY MAGUIRE (1996)

Well, well…Cameron Crowe, we meet again. It is really amazing to see how he is able to consistently bring out the raw emotion, charm, and character of his actors. Truthfully, Jerry Maguire, written and directed by Crowe, would be toward the top of the “Dude’s Rom-Com” list if this was a ranking. In the real world, romance doesn’t happen in a void, and Jerry Maguire intertwines the love story with the backdrop of striving for success in one’s career and the difficulties of single parenting. It also reflects our own shortcomings in trying, and often failing, to do things perfectly. The chemistry, subtlety, and passion expressed by Tom Cruise, Renée Zellweger, and Cuba Gooding Jr. is pure magic! Another quotable gem that will go down as not just one of the best romantic comedies of all time, but one of the best films ever.

WHAT WOMEN WANT (2000)

I have often wished that the one egotistical D-bag that we all seemingly must suffer in our lives might get the same power that Nick Marshall (Mel Gibson) is “blessed” with in What Women Want. Although, it may be a power all men have wished for at some point in time, we learn (as life often proves) it’s not that simple. Much to his chagrin, Gibson’s character finds out that he isn’t “all that and a bag of chips” (man, I feel old). There may be some dangerous generalizations made during this film, but there are also some important insights into the female psyche that, I’d hope, most men can appreciate. Add in the lovely Helen Hunt and Marisa Tomei, along with some “manly” wine-drinking while listening to Frank Sinatra, and I can’t think of any other selling point you need to make this a must watch.

HITCH (2005)

Hitch might not spring to the forefront of your mind when you think about romantic comedies that guys might like. When I first saw it, I thought I wanted to be the super cool and debonair Alex “Hitch” Hitchens (Will Smith), a man who knows exactly how to make women swoon with seemingly zero effort. By the end of the movie, though, I found I wanted to be much more like the sincere Albert Brennaman (Kevin James), the guy who gets the girl exactly because of his faults. By showing vulnerability, his special someone feels seen, believing that she too can be herself while with him. What truly makes this such a great date-night movie is its focus on both men’s and women’s struggle to impress, highlighting that what really matters is just being true to oneself and not taking yourself so damn seriously.

WEDDING CRASHERS (2005)

Vince Vaughn, Owen Wilson, Rachel McAdams, Isla Fisher, Bradley Cooper, Will Ferrell, Christopher Walken…do I really need to keep going?! If this all-star cast isn’t enough to lure you, the awesome premise of crashing weddings to seduce women through outrageous lies should be. Wedding Crashers explores finding love through the tinted backdrop of a fiercely enforced Bro Code and the navigation of extremely tough family dynamics. For our purposes here, this is a guy’s dream as both a hilarious, sex-oriented comedy and as a traditional “chick flick.” In a world where rom-coms have become extremely formulaic, it is so refreshing to get one that is novel, laugh-out-loud funny, and will have you quoting from it for years to come.

CRAZY, STUPID, LOVE (2011)

Let’s see, I’m at the end, and I haven’t named a Ryan Gosling or Emma Stone movie. How can I fit one in? Hmm…I know La La Land doesn’t quite fit in this category…. ooh, ooh, Crazy, Stupid, Love!! Another crazy ensemble cast carries this complicated love story with a web of intertwined relationships that results in hilarious confrontation. The actors’ timing, comedic or otherwise, is one to behold, and the cast chemistry allows everyone a chance to shine. What’s more, you won’t walk away thinking you were pacified by the usual romantic comedy clichés, instead getting real, meaningful, and beautifully messy human connection that is a welcome reminder of what really matters.