My Very Worst Date Moves

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Living Just Enough for the City

When I lived in New York City, I actively dated on Match.com. My Very Worst Date happened when I met a guy at a Union Square restaurant. I walked in and saw a guy sitting at a table looking around, but he was clearly 10 years older than the photo he’d posted online. His hair was also much thinner, but I decided to give it a shot anyway and introduced myself.  The waitress came right over and asked if we would like anything to drink.

"No, we don't want any cocktails," he said rather curtly. 

I let it slide because I thought he might be an alcoholic for a second. Still I was annoyed that he spoke for me.

"Well, can I order a soda then?" I asked.

"Do you have to?"

I was turned off by his cheapskate ways but I still tried to enjoy the rest of the meal since he seemed fairly charming otherwise. After dinner, we stepped out of the restaurant into a rainy, rainy night. Since we were both headed to the Lower East Side, I suggested we share a taxi.

"Do you have your Metrocard with you?" he asked. "Because we're taking the bus."

I had one in my back pocket, but I was shocked that in the cold rain he would want to wait for a bus just to save a couple of bucks.

"And is it one of the unlimited ones because I forgot mine?" he added.

I gave him the card, which had four bucks left on it, and I hopped in a cab to meet my girlfriends.

A Couple We Can Believe In: Unmarried Bliss

After playing lovers in the 1988 baseball film Bull Durham, Susan Sarandon and Tim Robbins became a real-life couple. Susan has said that in some ways Tim, who is 12 years her junior, is "older and more traditional" than she is. A dad to two of Susan's three kids, Tim says, "Age hasn't been a factor." He directed her Oscar-winning performance in Dead Man Walking and the duo regularly makes headlines for their anti war activism. While the New Yorkers have never married, they remain more committed than ever as they go into their third decade together. 

Dynastic Cabin Fever

Sometimes a Very Worst Date happens outside the traditional 'dinner and movie' set-up. Your romantic hopes might be crushed earlier or later on. So we present our first Mid-Courtship Disaster...

For the first time in my life, I found myself thrilled when the flight attendant showed me to my seat. I was flying business class for work and expected everything to be a little classier and better looking but my neighbor exceeded all my hopes of a glamorous traveling companion.

Not only did he look like an South Asian version of John F. Kennedy Jr., he was also reading a book about surgery. I silently thanked God for the blessing he’d delivered to me. Now we had the entire New York-Los Angeles trip to get to know each other, I thought as I settled in. The promise of his looks was fully fulfilled in his personality - he was remarkably erudite and stunningly intelligent. By Las Vegas, I was ready to marry him.

Before we alighted at LAX, he gave me his number. That's when he dropped in another number: his age. I knew the guy was younger than me so I guessed late 20s. I was older (in the next decade) but not by that much so I did not think it was that disgraceful - until he revealed he was 18. His parents had been several rows ahead of us on the plane!

After I’d finished up with work in L.A., I decided to call him on the urging on my colleagues, who cheered loud and excitedly, "Why not?" We ended up going out to fancy restaurant, where the reality of his age came home fully. 

When the waiter came up to ask if we wanted cocktails, I held my breath. He ordered a soda and later, he charmingly and thoughtfully discussed how he’d spoken to his friend about me and how they’d weighed up the relationship’s possibilities of working out. 

For me, this was not My Very Worst Date in the traditional sense, but it was still something of a dating tragedy. I was crushed. I met the man of my dreams and he turned out to be a boy of 18. 

On the Prowl

Lamenting the end of Rock of Love Bus? Those matchmaking reality shows not cutting it? Well, tomorrow night TV Land PRIME's debuts The Cougar, hosted by Vivica A. Fox (genius casting there). The new show, from the creators of The Bachelor, claims it's eager to shatter dating stereotypes (cougar-iffic Stacey thinks age is a number and there's a double standard on women who date younger men). Essentially, 20 younger dudes compete for the mother-of-four's heart, and there's even a set of 25-year-old twins in the mix. Then there's SNL's recurring "Cougar Den" sketch. And later this year, Courteney Cox Arquette will star in the risque ABC sitcom Cougar Town. While the Hollywood trend feels a little late to us (we've seen cougars in the wilds of Newport Beach, Beverly Hills and Manhattan for quite some time now), at least 40-plus gals are getting TV jobs. 

Wandering to the Folks

After I ended a long relationship, my best friend from college thought it would be a good idea to fix me up with her boyfriend's childhood buddy because we were both wine connoisseurs. I agreed. 

The location of our first date was a wine cafe. It did not start well. Within five minutes of the date, he was already pointing out that I had a "terrible habit of biting my nails." I was troubled by this critique but ignored it and the other small comments that danced on my nerves.

After lunch, he suggested a walk. I'd had too many glasses of wine so I agreed even though I knew the date was going nowhere. On route, he asked if I would mind stopping at his old friend's house for a minute. I didn't mind especially since he came into town for the specific purpose of our date. 

We approached the house and rang the bell. An older couple answered the door, which totally confused me. It took me a while to realize that they were his ex-girlfriend's parents, who clearly were not over my (apparently highly eligible) date. 

We sat at their outdoor bar (drinking beer mercifully!) for two whole hours discussing how he would one day marry their daughter and how wonderful their relationship had been.

I have never felt more uncomfortable in my life. This dude still wants to know why I never called him again.

In the Waiting Line

When I was 15, I met this guy while standing in line for tamales on Christmas Eve near my house in Texas. My parents habitually bribed me to wait the three hours it took to procure the best tamales in town during the holiday season.  Although this guy had two first names, instead of a first and last name like any reasonable person (a guaranteed sign of trouble in the south), he seemed nice enough, so I gave him my number and we went out later that week. But it soon became apparent that this guy was still terribly torn up about his ex-girlfriend and I think he tried to recreate the closeness of that bond the only way a 16 year-old boy knows how: in turn painfully over-sharing embarrassing details about his life and bragging about his sports prowess. 

This led to a 45-minute discussion about the joys of pole-vaulting, as well as an admission of bulimia, all while using a tiny can of breath spray as he talked. After I turned down his kind offer to see a picture of his ex-girlfriend and go park somewhere, he decided to continue the date at Wal-Mart, where he bought a CD that reminded him of some school dance he went to with his ex. While driving me home, he put in said CD and started crying. After he dropped me home, I realized that I forgot my jacket in his car.  When he turned his car around to bring it to me, he said, "It must be fate," to which I replied, "No, it's just forgetfulness."