40 Dates and 40 Nights (Delaney, 2026)
40 Dates and 40 Nights is a film so generic in its conception and structural organization that I didn’t quite believe I was enjoying it until the final credits rolled. It even shares its title with another romantic comedy, filmed and released twenty years earlier.
Bailey Madison plays Leah, a woman old enough to have lost hope that the modern dating scene is anything other than a pointless wasteland of frustration and disappointment but young enough to not yet be reconciled to the idea of settling out of despair. When she threatens to tap out of the dating ring, her Aunt Gigi (Annie Potts) makes her a wager that if Leah goes on forty dates and doesn’t end up with a suitable partner, Gigi will pay her rent and student debt. Once the wager is underway, all that is left is to guess which of the forty will be the magical one. For the record, that will be Mason (Joel Courtney).
Roger Ebert is generally credited with the observation that the central problem of a modern romantic comedy is not how to get the lovers together but how to keep them apart. In an age and culture where most heterosexual characters have the freedom to love who they wish, it is increasingly difficult to make one or both potential matches oblivious to the chemistry and fit the audience needs to see in order to root for them to get together. Typically this is accomplished by making one or both of them idiotic, either refusing to recognize the qualities of the other or ignorant of some horrible deficiency in a current partner that makes them temporarily inaccessible for a new relationship.
It is to the credit of Sarah Howard’s screenplay that we get neither of these common tropes. Howard goes the Jane Austen route of bad first impressions (the original title of Pride and Prejudice). The key point for me, however, is that the fault lies a bit more on her side than his. She has a couple of relatively small misreads and judges him harshly even though the viewer can see that he is not the jerk she has him pegged as. Once she knows better, she is in the middle of her string of dates and just cares about quantity over quality. The sooner she can get to number forty, the sooner she can ditch the dating thing entirely and not have to waste her energy on a series of losers.
If the film breaks the genre mode a little by allowing Leah to be less than perfect, we forgive her because we certainly empathize with her feeling that the dating scene she is so anxious to ditch is a soul-crushing grind. But even in making dating systems, rather than any one date, the antagonist, the film still treads lightly. We get just enough of the other dates – guys too cheap to pay, too narcissistic to care, too eager to let her breathe, that we understand Leah’s desire for something more authentic. Too much of this would play well as satire but would risk turning into a commentary on men as opposed to one on dating. By letting Leah be a bit of a jerk to Mason, at least to start, the film suggests that some of the most annoying habits, by men or women, are not so much intrinsic to their gender as it is the eventual byproduct of putting yourself out there until there is not enough of you left to interest yourself, much less a stranger.
In most romcoms where the plot is generic or the characterization slight, it is typical to say that success rides on the “chemistry” between the potential lovers. Madison and Courtney are likable enough and capable of knowing what flirting looks like. I doubt the movie works if they aren’t young and hot, and I do get weary of the genre conceit of the most beautiful people in the world wishing they could find someone, anyone, who will love them for who they are. Imagine how hard it is for those of us who don’t look like models and Hollywood stars. Still, misery loves company, and hope springs eternal. At heart, the message of the movie is one I can endorse – dating can suck, but so does loneliness. And if you stop looking for what you want, you’ll never find it.
Oh, and the more people you are nice to, whether you think of them as potential mates or not, the more likely you are to have and recognize a connection when life does put someone compatible in front of your face.
