Jessica Grose has a pretty funny article in Slate about what makes a bad date movie... and I think she more or less gets the tone right.
Guys: stay away from the overly sexual, or the overly gloomy. It just won't do you any favors. I speak from experience in these matters.
I once took a girl to see Boys Don't Cry -- which was a twofer on that count. It was the story of Brandon Teena, the girl who passed herself off as a boy (she hoped to have sexual reassignment surgery) and who, upon being discovered, was raped and murdered. I remember sitting in the theater during the rape scene slowly sinking in my seat, and being ashamed of all men everywhere. "Do you want to go?" I whispered to my date. (I sure as hell was having trouble stomaching it.) She shook her head, and we both endured the rest of this unpleasant film in silence.
One should also be wary of an upbeat ad for a movie. I remember seeing the trailer for Your Friends and Neighbors, and thought it looked cheerful and somewhat innocuous -- like a Woody Allen movie or something. I should have paid more attention to the fact that the film was directed by Neil LaBute. And I should have read a review. (This is very important, guys!) But the men in YFAN were the most nauseating, misogynistic vipers you'd ever want to cross paths with. While you don't see anything quite so revolting on screen as the rape in Boys Don't Cry, you might as well have seen something that vile when Jason Patric describes raping a boy in gym class. Ugh.
And sometimes the bad date movie doesn't have to be all that vile or disgusting to be too much of a downer to ruin a date. I once took a girl to see The Talented Mr. Ripley, which was not that bad in terms of horrible things happening on the screen. There are a couple of murders, but I think we both understood that going into the theater. But it was just so dark and gloomy -- with so many homoerotic undercurrents -- that neither my date nor I were exactly psyched to talk about it after the fact. We just sort of parted ways and never spoke again.
If you'll notice one theme to all of these movies, it's this:
They all came out in the late 1990s. I have learned my lesson and since been careful about which movies to invite girls to.
But I will say this: I sort of liked what Grose said about taking a date to see Capturing the Friedmans. No, I probably wouldn't take a date to see that movie... but if I did, I would be interested to hear what she had to say. And, yes, I agree philosophically that if you did have a spirited, fascinating, nuanced conversation, I think it would speak well of the girl, and well of your future prospects. One of those "high risk, high reward" sort of deals. But don't say I didn't warn you.