The Worst Dates Were Probably All My Fault

Writer/television producer Jeff Dugan’s been on some great dates, but he learned more from the bad ones.

Everyone has few good horror stories of dates that went awry. As I look back on mine, I have to admit the problems seemed to stem from some oafish action or oversight on my part. Here are my top 10 worst dates, in chronological order. Please, learn from them.

1) At age 17 I got my first car—an enormous 1970 Chevy Caprice with a 350 V8, four-barrel engine—and celebrated by asking a new girl out on a first date. I lived in Baltimore City. She lived way out Triadelphia Road in Howard County. The date consisted of a Beatles film screening in Towson. By the time I picked her up, drove us to the movie, then drove her home, I was out of gas. With no known gas station within miles of her house I had no option but to sleep on the couch in her living room. I met her unamused Dad for the first time the next morning when he asked me to move so he could read the newspaper.

2) The next year I was invited to another girl’s house for a formal dinner with her and her family. I managed to keep up my manners through dinner, but when her mom asked me afterwards if I’d like some coffee I blanched. I accepted her offer, even though I’d never tried coffee in my life. When the antique bone china cup and saucer were placed before me, I picked up the cup and swilled the scalding hot black coffee as if it were a can of soda. I burned my lips and mouth, dropping the cup, sending hot coffee and bits of her grandmother’s tea set across the starched white table linen.

3) Undaunted, later that summer I took yet another first date to see a little film entitled Looking for Mr. Goodbar. I hadn’t bothered to look up the movie’s description, assuming it was a comedy surrounding a candy bar. My date was horrified as we watched the tale of a young woman who seeks out abusive men for progressively violent sexual encounters before she gets brutally murdered on a first date.

4) By the time I was 22, a little older and more experienced, I asked a woman to go camping. Once again skipping the research, I selected a remote spot recommended by a friend of a friend. That night, huddled in our little tent, the only campers on the scene, my date and I discovered that the spot was popular because it was a well-visited site for partying bikers. Soon the noisy crowd in the nearby parking lot swelled into a feisty little army (much noisier). Determined to be chivalrous I took my date by the hand and we fled in the other direction, into the cold dark night. About a quarter of a mile away we came to a lone street lamp – but the light kept flickering. As our eyes adjusted we realized it wasn’t the light but thousands of bats swooping down from the sky. We ran to a lone trailer and asked to call the police, but the occupant threatened to shoot us at the count of three. By the time he got to two we were speeding off down a trail. I went back to the biker party, extricated my car, and picked up my date by the side of the road. We slept uncomfortably—and awkwardly—in a stranger’s driveway.

5) One balmy evening when I was 25, my date and I, both hungry and tired, debated about eating dinner before or after the movie we were about to see. “Let’s eat after,” I said. “That way we won’t have to race through dinner in order to make the show.” We entered the theater and watched a Japanese import called Tampopo, the two-hour tale of a truck driver who helps run a noodle shop, filled with endless scenes of savory food and happy diners. By the time it was over we were both famished and chewing on the seats.

6) I met a stunning woman during a business trip to Boston when I was 27. We connected immediately and made plans to go out that evening, despite a bad weather forecast. By this time I had learned the benefit of pre-date research and selected the finest club in town. I carefully mapped out the route and we set off…into a blinding snowstorm. After an hour of treacherous driving, we arrived at a rundown house in a derelict part of town, victims of my poor mapping skills. Back at my hotel she bolted at the first opportunity and the next day denied having ever met me.

7) By 32 my misadventures had gone international; after spending three weeks traveling through Italy, my girlfriend and I were desperate to relax, laugh, and hear a little English. In Milan, across the street from our hotel, a little cinema house was screening a lighthearted Robin Williams comedy, in English with Italian subtitles. The next night we ambled over, bought two tickets, and sat down ready to be entertained in our native tongue. Unbeknownst to us the theater had switched films that afternoon and we saw the opening sequence of a dark Robert DiNiro psychodrama, overdubbed in Italian. The highlight of our date was the ticket refund.

8) Ah, but by the seasoned age of 44 I’d become a spontaneous romantic. Stuck in Baltimore one Sunday afternoon emailing with a beautiful love interest in New York, I asked how she planned to spend the evening. “I’m ordering sushi from this great place then watching An Affair to Remember on TV,” she wrote. Flushed with a yearning desire I phoned her and asked if she’d like some company. She just laughed. I told her I was on my way and hung up. Within minutes I’d hopped into my car and sped north for the three-and-a-half-hour trek to Manhattan. By the time I reached New Jersey I phoned her again to make sure she knew I was serious. Again she laughed. The next time I phoned I was describing the color of the mat in front of her apartment door. I heard a mad scramble inside, as if her place were on fire. It turned out she hadn’t believed I would really come. I arrived at just about the same time as the dramatic results of her chemical face peel.

9) The next year in Chicago, yet another date and I were strolling happily along a promenade when I suggested we pop into a trendy bar to use the restroom. What was weird was that I saw a large red sign warning of two-way mirrors when I entered the men’s room. It turns out the toilet area was in a separate room, but the sink areas of both the men’s and women’s room had two-way mirrors in them. Sure enough, if I stood at just the right angle I could see into the women’s sink room as ladies powdered their noses and washed their hands. The big red signs were everywhere, but apparently my date was too preoccupied to notice. I watched her emerge from the toilet area, briskly wash her hands, fish into her handbag then proceed to pull out a tongue scraper and rake her tongue like a mad squirrel going after a buried nut.

10) By 51, over half a century of observing and learning failed me once again during the December holidays. Trying to be edgy I took a date to see raunchy underground Christmas review where the outlandish hostess poked holes into everything sacred, not noting that my date was a devout Catholic woman. Sorry about that one. Oh well, there’s always next year.

Jeff Dugan is a documentary television producer and the author of The Final Days of Jimi, Janis and Brian. Read more here.