Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.

Worst Pop-Culture Dates

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So many dates center around pop-culture: Two people going to a film, concert, comedy show, reading, museum, or what-have-you together. What stands out as your absolute worst pop-culture date?


Tasha Robinson
I covered my absolute worst with a story in the “worst filmgoing experience” AVQA back in 2009: The story of going to a Quentin Tarantino double feature where angry drunks who’d been kept outside in the cold for an hour started shrieking creepy sexist and racist things in the theater. It was a bad night outside the venue, and a bad scene inside. But we’ve been over that. So here’s a distant runner-up: Seeing the David Cronenberg Crash in 1996 with my boyfriend. It was just after Christmas, I’d just gotten back from a holiday with my family, and this was our first night out together since my return. Yes, the movie was sexually twisted and aggressive and off-putting from moment one, and not really what I was looking for in an emotional reunion or a holiday movie. More to the point, though, 10 minutes into it, I looked down and realized my wallet was lying open on top of my purse. Apparently the second the movie started, someone had slipped into the row behind us, winkled my wallet out of my purse, and taken the money out of it—more than $100, essentially my Christmas present from my folks, and a really significant amount to me at the time. When we looked around at the guy, he got up and ran out of the theater, so we chased him, called 911, and flagged down some cops driving by on the street. They were profoundly disinterested and sure the thief had already ditched his distinctive puffy white coat and was probably off robbing someone else, so there was nothing they could do. My boyfriend wanted to go back in and finish Crash, even though we’d missed half an hour of it at that point, but I was too shaken to watch James Spader have more alienating self-destructive sex. I never did see that movie—I still associate it with confusion, frustration, and violation, and not in the way David Cronenberg intended.

Kyle Ryan
In the summer of ’99, while I was sweating out a particularly hot Chicago summer in my un-air-conditioned apartment, I took in a lot of movies to escape the heat. My girlfriend and I wanted to see Summer Of Sam, and when her mom came to town, we decided we’d all go. This not being the first Spike Lee film I’d seen, I still can’t explain my shocking lack of foresight. Lee has never shied away from sex or sex talk, and few things are more awkward than watching a sex scene with parents. Lee treated us to several of them in Summer Of Sam—a sex club, some porno movies, etc.—along with some colorful dialogue, such as Mira Sorvino shouting, “I smelled her pussy juice all over your fuckin’ face!” I think I pulled a muscle in my back from cringing for nearly all of the film’s 142 minutes. My strategy was to hide my face in my soda cup, dragging out eating the ice for as long as possible. My girlfriend’s mom—now my mother-in-law—thankfully never brought it up. My wife and I never made that mistake again.

Will Harris
Throughout my single years, I tended to develop crushes on my co-workers. This panned out nicely in the end, but the running joke is that my wife and I worked together for six years before I ever got the nerve to ask her out, thereby proving conclusively that I am not what you’d call a fast mover. This is an absolutely true assessment of my romantic methodology, but immediately before she and I started dating, I proved to be so slow at indicating my intentions with another co-worker that, even though she knew I wasn’t gay, she apparently also didn’t realize that I thought we’d started dating. In retrospect, maybe it’s because Linda didn’t perceive what we were doing as dating—admittedly, we were a far cry from getting hot and heavy—but, y’know, I took her to a movie or two, I paid for the tickets, I put my arm around her and she snuggled in, and even though we hadn’t yet kissed, it was because I figured, “No need to rush this: We’re working together, so I’d better make sure there’s something there.” But when I heard The Ocean Blue was bringing its Britpop-by-way-of-Pennsylvania sound to Virginia Beach, I thought, “Okay, if there’s ever going to be a right night, this is it.” The show started a little later than scheduled, but the band sounded great, and we were hanging out, swaying to the music, and enjoying the jangly guitar pop. And that’s when it happened: she leaned over and said, “Do you mind if we leave in just a little bit? I promised my boyfriend I’d stop by before it gets too late.” It may not surprise you to learn that, after I regained the ability to speak, I said, “You know, actually, we can go right now if you’re ready.” To this day, I can’t listen to The Ocean Blue without thinking about that last night out with Linda, but there’s a nice bit of irony in the fact that the title of the band’s first single summarizes our brief “relationship” perfectly: “Between Something And Nothing.”

Josh Modell
The year was 1990. I had been dating my first real girlfriend (who eventually became my first and only real wife) for about six months. We were in high school. I guess I didn’t know enough about her tastes at the time—it was enough that she liked weird jokes and listened to New Order—so I took her, along with my mom, I think, to see Total Recall. The Ahnuld-starring sci-fi movie was tailor-made for 16-year-old me: futuristic, pretty damn violent, ridiculous. What my now-wife didn’t tell me until much later was that she was squeamish about violence and pretty much hated anything science-fiction related. It was pure torture for her, and I felt bad in that special way only teenage boys can. But still, she married me, so it’s all good. I just keep my dumb-ass movies to myself most of the time.

John Semley
Before I came to the eventual realization that I can actually find women who like me, warts and all, I used to do that really self-destructive thing where you orbit around girls you romanticized but know you’ll always only be friends with. It’s safer, you know? There’s a weird comfort in knowing that your desire runs one way and your stupid affections will always be unrequited. Then you can get off purging your soul by writing bullshit short stories and falling asleep drunk to Nick Cave’s “From Her To Eternity” playing full blast on repeat four nights a week. Anyway, the point of this is that one time I took one of these poor women on a halfway-date to a goddamn Les Claypool concert. As the former bassist frontman for ’90s experimental alt-funk outfit Primus, Les Claypool is basically an anthropomorphic bong who wears gross-out pig masks onstage and is regarded as one of rock’s premier bass players. I was clearly hoping that… well, I don’t really know. That I’d impress her with my knowledge of shroomy goofball bassists? She did the only sensible thing and excused herself, while I nodded my sweaty head to the syncopated slap ’n’ pop rhythm of Fancy Band-era Les Claypool and wondered just what the hell I was doing with my life.

Kenny Herzog
Isn’t high school pretty much one hallucinatory string of these after another? I could discuss my attendance at a double-date screening of Barbra Streisand’s The Mirror Has Two Faces, or a hardcore show at which I haplessly witnessed my then-girlfriend get booted in the gut by an unwieldy windmill-kicker. For that matter, there was my trip to the movies with a girl who was on crutches, and my failure to avoid letting the multiplex door slam behind me into her already-hobbled midsection. But my personal favorite would be the decision to venture on a blind date facilitated by mutual acquaintances and lots of AOL instant-message exchanges about our mutual interest in shitty music and feeling sorry for ourselves. We went to see Air Force One. Seriously. And had nothing in common and absolutely zero attraction to each other. Besides, nothing says “Let’s make out inadequately in my Nissan Sentra afterwards” like a middle-aged Harrison Ford growling, “Get off my plane” at Gary Oldman’s Kazakhstan terrorist. That entire night was the sound of an erection dying.

Todd VanDerWerff
In early 2000, my girlfriend’s grandmother had just died. Her grandmother had been a touchstone in her life, someone she had always been able to turn to, despite being part of a large family, where it was easy for a middle child to get overlooked. She was, understandably, distraught. I came to pick her up after the funeral, then suggested we head up to the nearest city to see a movie, to take her mind off of things. My choice was Paul Thomas Anderson’s Magnolia, which I’d been wanting to see ever since I started reading early reviews of it on (sigh) Ain’t It Cool News. Magnolia is a lot of things, but it’s also an unrelenting barrage of a three-hour film that keeps hitting you in the face with stories about dying parents who have failed their children, or about sad, depressive people, clinging to the bottom rungs of American life. I loved it—still do. The girlfriend was considerably less enchanted, offering up a few praises because she knew I wanted to hear them, then mostly staying silent as we drove back to college. It was only years later, after we were married and I couldn’t get her to watch the film with me on DVD, that I realized, hey, maybe she’d had some other stuff going on that night. She still hasn’t re-watched it, and maybe she never will. Sorry, dear. (Sadly, this is my bad-pop-culture-date story that makes me sound the least like a dick.)

Noel Murray
Right after college, I waited tables at an Applebee’s in suburban Nashville, and for a few months, I dated a fellow server: a conservative Christian who was looking to be a professional singer, preferably on the stage. (Which, if you know anything about professional musicians, means that that, to quote The Hold Steady, “She was a really cool kisser / and she wasn’t all that strict of a Christian.”) On our nights off, I used to get movies from the Blockbuster where I also worked at the time and brought them over to her apartment. One night, I brought over Roger & Me, which I thought of as a funny movie with some good points to make about how the working man gets screwed. It honestly never occurred to me that my date would find the movie offensive, both for its sarcastic tone and its point of view. (Not to mention those poor skinned rabbits.) We’d never really talked about politics or religion; we mostly just drank, watched movies, and made out. Needless to say, that night, her icy reaction to the movie precluded the other two activities. But she got even. On my birthday about a month later, I wanted to go see Steely Dan, who had just reunited for a rare tour. Instead, she took me to see a local production of Nunsense. We broke up about a week later.

Zack Handlen
The bit in The Dark Knight (which I never saw with a date) where the Joker talks about being like a dog chasing after cars is pretty much me with girls for my entire adolescence. I was hell-bent on catching one, but I had no idea what to do when I actually convinced someone to go out with me. On my first (and only) high-school movie date, I took my first (and only) high-school girlfriend to go see The Birdcage. It’s not the worst movie ever, but it is a weirdly sexless farce (apart from Hank Azaria’s shorts), and I think we both felt like we had to pay respectful attention the entire time because Tolerance Is Important. I remember being terrified there was some sort of proper date-movie etiquette I wasn’t handling properly, and wanting to kiss my girlfriend because I heard you did that in movie theaters and it sounded fun, but also not wanting to interrupt her if she was paying attention to the movie. I didn’t get any better at this in college. The only date I went on in the whole four-year span was during a summer break, when I took a girl I worked with to see Eyes Wide Shut. Again, not the worst movie ever, and in some ways, it’s a better choice than Birdcage, because at least there’s some hotness on screen, even if it’s all deeply ironic and conflicted and sort of makes you feel like a piece of meat. But it set a tone for the evening which made us both uncomfortable afterward, and when I told her I wasn’t sure it would work out, she seemed entirely okay with that.


Sam Adams
I’ve never been great at thinking about cultural objects in practical terms. To me, a great movie’s a great movie, and whether it not it might be appropriate for a given occasion doesn’t really enter the picture. So when I was looking for stuff to do with that girl I kind of liked, I thought, “Why not meet up at a film-festival screening of Time Out? Only afterward, as we stared at each other with shell-shocked eyes, did it occur to me that perhaps a French movie about a man who lies to his wife and sleeps in his car rather than admit he’s lost his job might not make for ideal date-type banter. In my defense, I hadn’t thought of it as a date per se, just that this woman I’d met a few times seemed interesting and I wanted to spend time with her, but something told me I didn’t want the encounter to end with both of us looking like a relative had just died. I hastily proposed a post-film dinner at a nearby diner, and then—hey!—stopping by the Clinic concert, where I’m sure I thought my ability to get us in free would seem endlessly impressive. The jury’s still out on that part, but it turned out all right eventually. Reader, I married her.

Jason Heller
I’m not sure why I thought a movie—any movie—titled The War Zone was going to make for a great first date. But before its release, I’d heard the 1999 film was a little British indie picture directed by Tim Roth, and that seemed to be enough to send me and a girl I’d had a crush on for months to the local Landmark theater to get acquainted by sitting in the dark and not talking to each other for two hours. So on opening night, we got tickets, bought popcorn, and settled into our seats for some presumably weepy, sensitive melodrama set in the picturesque English countryside. Well, it was weepy all right. In the wrong way. The story (which I would have known, had I had the foresight to read Alexander Stuart’s original novel and/or a review of the film) is about incest. Brutal incest. And lots of it. Yes, The War Zone, as we quickly came to find out, is about heaps and loads of brutal, horrific incest perpetrated by a man against his daughter, all set against an ethereal backdrop of cliffs and drizzle and wails of misery. Afterward, credits rolling, we pried our fingers from our armrests and stood up to leave. The look in my date’s eyes wasn’t exactly what you might call lovestruck. We talked over each other trying to make excuses to cut things short and go to our respective homes, and we never saw each other again. In hindsight, I’m just glad I had the good sense not to try holding her hand during the movie.


Joel Keller
She was a pharmacist who worked with my mother, and I was at a low point in my dating life. She seemed perfectly nice, though, so with a “What the hell? I can’t do any worse” attitude, I told my mother to set us up. After talking on the phone and exchanging e-mails, we went to a fairly inoffensive Italian restaurant, where we had a nice but not very interesting conversation, then a movie. That movie was Connie And Carla, Nia Vardalos’ follow-up to her mega-hit movie My Big Fat Greek Wedding. I hadn’t seen Greek—still haven’t—and had little desire to see a story about two women (Vardalos and Toni Collette) passing as drag queens in a cabaret act to hide from the mob. But on a first date, you don’t have much control over what you see, if you’re the guy. I didn’t laugh once, but my date did, and about midway through the movie, I started wondering if the reason my mother liked this woman was because they had similar tastes. I’d like to say the night ended after the movie, but I was on such a dating dry streak, and she seemed to dig me, so we went back to her place and made out like our plane was going down while Saturday Night Live played in the background. As I left her apartment and went into the snowy night, she eagerly asked me when I could go out again. “I have to check my schedule,” I said flippantly. Needless to say, we never saw each other again.

Keith Phipps
I guess buying her a Kris Kristofferson album she already owned was my first mistake, but not my last. She was political and seemed pretty openminded, so I took her to a foreign film. (I think it was Swedish. I can’t remember the name. Love something?) We arrived late and it was already showing, which I guess didn’t help. But for some reason she wouldn’t even watch five minutes before she wanted to go. The date ended early. I saw her again a little bit later, and it was pretty awkward.