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." 

A Couple We Can Believe In: Just The Two of Us

How smoking are these two? So much so that the rumor mill can't stop speculating that Will Smith and Jada Pinkett Smith are really a gay (or bisexual) couple married in heterosexual and career convenience. Pinkett Smith recently brushed off the titters in an NPR interview (no less!), where she basically said: you can believe us or you can lump it. 

With that out of the way, we can proceed. Smith met his pint-sized princess (and former Miss Maryland) on 'The Fresh Prince of Bel-Air' when she auditioned to be his onscreen girlfriend. She didn't get the role but got her prince. Twelve years on, the two have a couple of kids, genre-jumping careers and a marriage that's apparently as rock solid as Pinkett Smith's biceps. 

Their secret? She has said utter commitment to the union. Smith's mentioned that they've studied why Hollywood couples break up and have learnt from that. He also told a U.K. tabloid magazine that he'd tell the wife if he wanted to sleep with another woman last year. No word though if he has - or if she's done the same. 

Perhaps it's not the swinging open marriage that gossip purveyors have in mind but the two might just have the kind of crystalline communication that most of us crave. They even tell each other who they have celeb crushes on (him: Beyonce, Salma Hayek; her: The Rock). But we can only imagine that their "I like her/him.." conversations end with "...but I love you."

The Human Stain

I was on my second date with a guy I really liked. We had a wonderful dinner at a nice hotel and then moved to the nearby lounge for drinks afterward. I was sitting on a white couch and it was pretty warm outside this particular evening. After a few moments I looked down and realized that there was some sort of orange stain on the couch. Then it occurred to me that I was actually the cause of this. I had gotten a spray tan in preparation of the date, but now I was basically sweating it all off right onto the pure white couch. My date nicknamed me “Oompa Loompa” that night and I thought I was going to die of embarrassment. Luckily he didn’t mind too much because we are still together three years later. 

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Call Back Blues

You thought the first date went well. So why then are you still waiting to hear back from your potential beau? A new book called Why Didn't He Call You Back: 1,000 Guys Reveal What They Really Thought About You After Your Date by dating coach Rachel Greenwald [first tome: Find a Husband After 35 (Using What I Learnt in Harvard Business School)] out today attempts several answers: you were a bossy boots, you were too full of the blahs, drank too much etc. In short: you were a bad date. The book reminded us of a more literary take from another era altogether on the no-phone back phenomenon by famed wit Dorothy Parker. Her short story A Telephone Call is a stream of consciousness soliloquy by a woman praying (and waiting by the phone) for a dude to ring her back. It's hilarious, painful and pathetic. A cautionary tale if there ever was one.

Not a Smoothie

In a fit of internet dating in college, I agreed to meet up with a fellow. We'd talked online and over the telephone, and seemed to have enough in common that getting together for smoothies was not out of line. His request to meet me in the produce section of a local market was odd, but I tried to chalk it up to just being quirky-cute. I arrived early to scope out and five minuets later, there was a guy hanging out by the starfruit. When I squinted and turned my head to the side, I was able to see how this individual was related to the photograph online, but it was a stretch. I made my approach and introduced myself. He was much more nervous than he was on the phone, and had made me a mix CD full of really romantic stuff. Eek. 

The conversation over smoothies was nice, but I wasn't really feeling it. I'd taken the bus to meet him, and he offered me a ride. At that point, I was still down for hanging out, so I accepted. We started to drive and he mentioned that he had gone by the liquor store to "stock up for when we went to his place that night." I took that as my queue to tell him that he could just drop me off at my house. He agreed, and the rest of the drive went by in silence until we were about five blocks from my residence when he turns to me and breaks the silence, saying, "So... you're Jewish?" I blinked at him, surely with an open mouth, and finally said, "What?" I had never told him what religion I was. He stammered, "Well, you know... uh, dark hair and, your, uh... big nose.... um. Uh. I guess you're not?" I told him that the next corner was fine, hopped out of the car, and walked the remaining blocks back to my place.

Chicago with a Side of Whopper and Fries

My first mistake was allowing my parents to set me up on a blind date. The guy picked me up and informed me that we were going to a Chicago concert. I was not that keen on the band but it was a free concert and we had great seats. 

It turned out to be a total bust. My boy sat there not clapping, not singing (who doesn't know the words to Hard to Say to I'm Sorry?) and definitely not moving, never mind swaying or dancing. 

On the way home, he told me he wanted to grab food and drove up to a Burger King drive-thru. At this point, I was shocked to silence. He ordered his food and then casually asked me if I was hungry. I told him I was "fine." After getting his meal, he drove to his house, got out of the car and made his way inside. I had no choice but to follow him. 

He finally wolfed down the Whopper and fries and offered to take me home if I wanted him to. Um yeah! At my front door, he asked me if I wanted to go out again next weekend. I told him no, I didn't want to ever go out with him again. 

I heard through the grapevine that he's now married. I wonder how often he and the wife eat at Burger King...

Un-Date Action

While I was grabbing coffee before class, a cute enough, well built guy came up to me. We chatted a little and I gave him my number. He seemed normal enough. He called and we organized to meet up at the grad students' lounge and head to a party the following Wednesday. I don't like house parties but I figured I'd try to be open minded. And birthday parties are always kind of festive, right? 

When I arrived at the lounge, he was sitting by the fire. Half asleep. Lovely. He woke up and proceeded to pound three beers (to my one glass of white wine) and then insisted we do Jager Bombs. Then he began a monologue about industrial music. For the record, I am a slummy hipster. I don't like industrial.

After texting incessantly while we sat there for about an hour, he announced that we had to leave for the party NOW. We rushed into a cab and headed off. He stopped at a liquor store, and asked me to pitch in for booze because he was "broke." Perfect. Then, after some detours, we finally found the house (he'd copied the address down wrong). At that point, he realized he did not have enough money to pay for the cab. 

I paid and tried to remain optimistic. I realized that we were in an icky part of town that I did not know well but still I was ready to party. We entered the house and there were a grand total of four people there. They were trashed and wanted snacks. So my "date" and the two girls left for the store, leaving me there with the host, who regaled me with tales of his recovery from meth addiction and his former penchant for visiting prostitutes. 

When the others got back, I escaped to the restroom and texted eight different friends telling them to call me and pretend to be my roommate. My friend A graciously obliged and informed me that our pipes had burst. You see, since she was not good in a crisis, I had to go to her. I got in a cab and got the hell out.

But before I did that my companion for the evening walked me out to the cab. 

"Is this a date?" he asked.

"No, it's not," I replied affirmatively.

He proceeded to assure me that he would call again. 

My response? 

"I wouldn't."

Getting Personal

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.