Mistake #1: Picking the Heavy-Duty Bummer
A date night is usually not the time for a soul-crushing examination of the human condition. You want to leave the theater with something to talk about, not a shared sense of existential dread. While critically acclaimed dramas are great, some are simply
too intense for a lighthearted evening. This fall, be wary of films that sound like a homework assignment in melancholy. For instance, Mahershala Ali stars as a devout hitman in Your Mother Your Mother Your Mother, which sounds like a gripping but emotionally taxing journey. Similarly, Paper Tiger, a drama about brothers entangled with the Russian mafia, promises grit and tension that might not scream “romance.” Unless you and your date have explicitly discussed a shared love for intense, dark character studies, it’s often best to save these powerful films for another time.
Mistake #2: The Extreme Genre Gamble
There’s a big difference between a fun seasonal scare and a full-blown gore-fest. Misjudging your date’s tolerance for horror or action is a classic misstep. This season’s reboot of Resident Evil promises a viral outbreak and infected monsters, a premise that could be a blast or a complete nightmare depending on your partner's sensibilities. Likewise, the survival thriller Whalefall, in which a diver gets swallowed by a sperm whale, is built on claustrophobic tension that might be too much for a casual night out. And Adam Wingard's action-thriller Onslaught features a sniper battling genetically engineered super soldiers. These movies can be an absolute thrill, but they are a gamble. If you haven't confirmed your date is a die-hard fan of the genre, you risk them spending two hours with their eyes covered.
Mistake #3: Booking the Three-Hour Marathon
A great date movie leaves you energized and ready to grab a drink to discuss it afterward. A film that pushes the three-hour mark can leave you exhausted and checking your watch. The goal is to connect, and a marathon movie can eat up the entire evening, leaving little room for actual conversation. This November, The Hunger Games: Sunrise on the Reaping is set to be a massive blockbuster event, but it will also likely be a long and dense story that commands all your attention. Similarly, Digger, a film from acclaimed director Alejandro G. Iñárritu, has the feel of an epic that demands serious investment. These are perfect for a solo trip or a deep-dive with fellow fans, but for a date, a movie that clocks in closer to the 100-minute mark is often a safer bet.
Mistake #4: The Niche or Sequel Pick
Picking a movie you're passionate about is great, but choosing one that requires prior knowledge your date doesn't have can be alienating. A sequel is a prime offender. Practical Magic 2 brings back Sandra Bullock and Nicole Kidman, which is wonderful for fans of the original, but it might leave a newcomer feeling lost. The same goes for highly specific art-house films. A quiet Korean drama like Lee Chang-dong’s Possible Love could be a beautiful experience, but only if both people are on board for a subtitled, meditative story. Before you select a sequel, a foreign film, or a documentary about an avant-garde filmmaker, have a quick chat. The goal is a shared experience, not a pop quiz.
Mistake #5: Assuming “Comedy” Is a Safe Bet
Not all humor is universal. One person’s hilarious satire is another’s awkward cringe, and a comedy that misfires can create a uniquely uncomfortable silence in a dark theater. While a good laugh is the ideal outcome for a date, you need to consider the type of comedy. For example, a film like Ali G: Who Iz I? relies on a very specific, provocative style of humor from Sacha Baron Cohen that isn't for everyone. Likewise, the success of a relationship comedy like Tyler Perry's Why Did I Get Married Again? often depends on an appreciation for the franchise's specific tone and characters. Instead of just looking for the comedy label, aim for something with a broader appeal—think a high-concept buddy comedy or a well-reviewed rom-com that doesn't rely on overly niche or divisive humor.
