Sunday, April 19, 2009
Friday, April 17, 2009
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.
Thursday, April 16, 2009
Wednesday, April 15, 2009
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.
Tuesday, April 14, 2009
Monday, April 13, 2009
Friday, April 10, 2009
Thursday, April 9, 2009
Wednesday, April 8, 2009
Tuesday, April 7, 2009
Monday, April 6, 2009
Friday, April 3, 2009
Thursday, April 2, 2009
Wednesday, April 1, 2009
In the mid-90s I was 19, I had just come out of the closet and was taking six weeks of summer school in Ohio and there were very few people on campus. I picked up an alternative free city paper and discovered the personals section in the back. So I brought it back to my dorm and placed one because it was free. A few days later I had a message from this guy and we had a good chat. He was in his early 30s, but I didn’t mind the age difference. Since I didn’t have a car, he offered to pick me up, so I sat outside the student union and this red Toyota Celica pulled up. “Fuck,” I thought to myself as soon as I saw him. He was wearing acid washed tapered jeans, white sneakers and an open buttoned white shirt that revealed a black t-shirt. Oh and he had thick Coke bottle glasses and buckteeth.
Since I was the only person in the area and had told him what I looked like, I couldn’t get out of it. We went into town and I picked a place where no one could see us. He ordered spinach dip, but managed to get it stuck in between his teeth. He snorted while laughing and proceeded to reveal that he was divorced and still lived with his ex-wife who was actually a post-op tranny. He said he married her because she needed a visa and he “really liked trannies.” The sad thing was that he had no clue I was having such a miserable time. He insisted on stopping for an ice cream sundae at Friendly’s before dropping me back at my dorm and I didn't argue because this guy could have easily driven us into the woods and I would have disappeared. He told me he’d love to see me again, but I told him I just didn’t feel a connection. I avoided personal ads from that day on.