Date Night: A Reel Guide to Romance

By Natalie McCarty

Every year, like clockwork, the temperatures drop, and so begins the warming trend in relationships. There’s an undeniable magic in the air during the holidays, a magnetic force that draws people closer. Maybe it’s because winter tends to amplify our sense of loneliness, with the vibrant activities of summer replaced by a cold chill that urges us indoors. The idea of hitting the club loses its appeal when you find yourself trudging across the dance floor, burdened by a giant puffer jacket.

That’s why movie date nights and cozy dinners witness a swift surge, while more activity-based outings take a backseat. Intimate conversations during candlelit dinners provide the perfect setting not only to deepen your connection with your date but also to assess whether they’re someone you want to welcome into the new year with.

I always love a movie date. Being a film enthusiast, it becomes a rapid compatibility test for me. How does this person watch a movie with me? Do they leave tasteful remarks? Draw quick parallels between the film’s events and our own current circumstances? Are they truly tuned in or just passively watching? Do they have the attention span for a full movie? Will they watch something that’s important to me, even if it’s not their usual taste? And most importantly, can we have a genuine conversation about it?

In my dating experience, I’ve found an unparalleled truth: the men who watch movies with me the best often turn out to be the best boyfriends. Their attentiveness, intelligence, wit, and humor shine through during these moments, revealing their true nature. Beyond that, the ability to find comfort in silence becomes apparent, and a shared rhythm in movie watching mirrors the sync in our relationship.

The girls at Gut Instinct have been talking, and it’s time to put our dates to the test. Stella and I have curated a list of our favorite chick flicks and true gems that have gone over well for those movie date nights.

Jerry Maguire will always hold a special place in my top four favorite films of all time, securing its spot as my ultimate favorite romantic comedy. Truly, it stands out as one of those rare movies that has a little something for everybody. I’ve yet to encounter someone who dislikes this film — it’s practically impossible.

With iconic lines like “You complete me,” “Show me the money,” and “Help me help you,” this Academy Award-winning film is equal parts hilarious and devastatingly romantic. Tom Cruise’s charismatic performance as Jerry and Renée Zellweger’s portrayal of Dorothy create a chemistry that is both entertaining and heartwarming. The mix of witty dialogue and genuine emotion ensures that you and your date will be thoroughly engaged throughout the movie.

Beneath its romantic comedy exterior, Jerry Maguire delves into the complexities of relationships, loyalty, and personal values. Watching the characters navigate these challenges can spark interesting conversations between you and your date. It’s a film that prompts reflection on what love means and how individuals grow within the context of a relationship. The character arc of Jerry Maguire, from a sports agent driven by ambition to a man seeking authentic connections, provides a compelling narrative. Witnessing this transformation can lead to discussions about personal growth, aspirations, and the importance of staying true to oneself — topics that can deepen your understanding of each other.

My high school boyfriend and I watched 10 Things I Hate About You and every time I think of this movie, it is what I think about. And honestly, it was a fantastic choice for a date night movie. The high school backdrop, the rebellious spirit of Kat, and the charismatic bad boy Patrick — each character resonated with facets of ourselves or familiar classmates. It’s a nostalgically charming watch, featuring delightful banter among characters, offering an easy viewing experience that leaves you with a warm, feel-good sensation (minus her iconic poem reading (I cried even though I had seen it before)).

Anyway, Stella and I both had 10 Things I Hate About You on our list. For beyond its entertainment value, the film subtly plants seeds of romantic gestures, both grand and subtle, serving as a gentle reminder not to settle for anything less. If a high school Heath Ledger could pull off such romantic feats, why shouldn’t a grown man with a mortgage aim for the same?

On a broader note, the movie functions admirably as a conversation starter, providing ample material for post-viewing discussions. Whether delving into shared high school experiences, matters of love, or personal growth, 10 Things I Hate About You enriches the post-movie conversation, making it an ideal catalyst for getting to know your date on a deeper level.

High Fidelity is the ultimate way to gauge whether your new relationship has successfully moved on from past romantic entanglements. Within the initial forty minutes, a keen observer can effortlessly discern the lingering echoes of an ex. In my personal experience, watching this movie on a date proved to be an interactive experience, with pauses every few seconds to delve into discussions about cherished songs and the intricacies of past heartbreaks. It seamlessly opens the door to exchanging intimate details about each other’s histories, transforming a simple movie night into a shared journey of self-discovery and mutual understanding.

Another of Stella’s picks that I absolutely adore is the hit early-2000s rom-com, 27 Dresses. Its got all of that good romantic comedy appeal–from a relatable storyline of Jane, who takes on the role of a bridesmaid 27 times, to the charismatic performance of James Marsden (plus his chemistry with Katherin Heigl’s character) — its engaging and heartwarming. Total classic for date night or even for a girls night in!

One of the finest films known to mankind is Rob Reiner & Nora Ephron’s When Harry Met Sally… It stands as the the quintessential romantic comedy, skillfully blending wit, charm, and undeniable chemistry between its leads, Meg Ryan and Billy Crystal. The film’s timeless exploration of friendship evolving into love elicits tears from me every time–though not quite The Notebook or La La Land levels, so you should be fine. This one is a true emotional journey, a hard-hitting experience best reserved for later stages in the relationship and not to be watched on the first date (unless you possess an iron heart and can make it through without sobbing).

When Harry Met Sally… is something you’d want to whip out while more settled and secure in your relationship, for sure. It underscores the importance of good communication, but also fun and friendship in your relationship. After all, how can you spend your life with someone you aren’t even truly friends with? With its relatable characters, sharp dialogue, and heartwarming moments, When Harry Met Sally… promises laughter, romance, and the perfect atmosphere for a memorable evening together.

One off of Stella’s list that I admittedly had not seen before was The Proposal, and I can’t thank her enough for the recommendation. Largely because I am a sucker for a film with the fake engagement plotline (another favorite being Adam Sandler’s I Now Pronounce You Chuck & Larry… sue me!!!), I found it wildly hilarious and not-overly romantic. Definitely could make for a good double date watch even.

I can’t overlook this film, and while it might sound like a joke, I genuinely consider the “Twilight test” a crucial criterion. My first real boyfriend set the tone for our first date with a screening of Twilight, and despite our long history, I’m convinced that moment was the catalyst for my feelings. Since then, it has become the penultimate test for compatibility in any potential relationship.

Twilight holds a special place in my heart and is my go-to movie for every occasion. I’ve shown it to everyone from dates, to my best friends, to a group of baseball boys, to colleagues… honestly the list goes on forever. I’ve even coerced my best friend Monet into watching every single one with me, and my seventeenth birthday was Twilight-themed, complete with punch served in blood bags and vampire teeth on plates.

There’s an inexplicable charm about Twilight. The first one is cinematically well-shot, delivering believable young love despite a few dramatic performances. It boasts an impeccable soundtrack and unforgettable scenes, and, although it may seem silly to some, the Twilight Saga holds sentimental value as a significant part of my upbringing.

Beyond preconceived notions, it’s genuinely a good film. If your date disagrees, at least it provides some fun banter. The film has undeniably become a major pop culture phenomenon, and I could passionately discuss its impact on pop culture forever (much to the dismay of my poor dates (just kidding, they all appreciated it & are all now fans of the series too)). With a bit of everything, it’s the one film I could watch endlessly.

If my high school boyfriend was willing to put in the effort to watch not just the first one but all of them with me, why shouldn’t every other suitor put in the same type of effort? Thanks for setting the bar there, pal.