Dating Disaster: The Date That Never Ended

Dating Disaster: The Date That Never Ended
Love, Heartbreak

If only she had seen the first date red flags...

Sure, he was tall, dark and handsome, and I looked good in my Tahari suit, handed down to me from My Sister's Closet. We looked like the perfect couple, and got all sorts of encouragement from our colleagues. One lady even admonished Brian (not his real name) to "make sure she gets to her car okay." A gentleman, I thought. Little did I know that he really fit the old-fashioned word; he was my senior by 35 years. A combination of hair dye, good vitamins and unclear communication had hid that fact for many years.

The plan was for Brian to drive me to my car, at another parking lot. When we got there, our high from the motivational speech had turned into trading stories about our bad jobs and future plans. "What a shame to cut it off at this point," I thought, and ignored the blinking clock. Red flag number one at 12:10 AM. Dating Disaster: His Name Wasn't Scott, Evidently

My eyes started drooping at 2:45 AM. I began wondering if it was a shame (or not) that our literature and philosophy chats kept getting cut off for the tyranny of urgent meetings. We'd been lightly flirting for months, but no action until tonight. Brian's promise of coffee at Denny's "later on" turned out to be empty. He barely had enough money for gas and shoe polish.

We stayed in that car until 5 AM. Brian had a lot of history to cover. His upbringing as a minor diplomat's son, his Stoic training at an English boarding school, his unbreakable rugby bones... all of this was paraded past my innocent nose while I would much rather have been snogging. "In for a penny, in for a pound," I thought, and remained awake by talking about my exes and the latest dipstick who'd hit on me at Starbucks. "He was a dirty old man!," I said, louder than necessary, and nearly hit Brian with a flailing hand. "He told me that he wanted to be 'much more than friends,' when we'd just been talking about his grandchildren." I snorted, then noticed Brian's sudden silence; perhaps he'd gotten tired. Red flags were waving vigorously, with nobody home to see them. Dating Disaster: He Froze My Match.com Account

"Do you need to get home?," I said nervously, wondering if I'd been talking too much. That's when I discovered that Brian was behind on rent payments, living on beans and rice and the surviving off of a severance package from his last job. Red flags began poking me in the eyeballs. Then he asked my opinion of Lord of the Rings and mentioned his custom surround-sound system that he'd crafted from vintage World War II speakers. Hooked again, the dumbest fish that ever swam the dating sea, I blubbered out my affinity with Lucilla from Gladiator, "I am tired of being strong." Brian pondered this thought. "I am tired of being weak," he said finally.

Saved by the sun peeking up at 5:15 am, I dragged my weary carcass home for two hours of sleep before work. Later on, I found out that Brian had driven blissfully into the sunrise, overshot a turn and totaled his car. Without insurance, he limped home on three wheels, leaking oil. As intended, this news made me feel sorry for him. Who else would patch up this broken-winged bird? "Anyone but you," a prescient voice murmured. But of course I ignored that wise whisper and then spent the next 12 months trying to closing down the date that Brian never wanted to end.

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