When I was 24, staring down the barrel at 25, I didn’t have a date for Valentine’s Day for the first time in my adult life. I had just broken up with random boyfriend number 14, and I was panicking. Not because I was afraid to be alone on Valentine’s Day but because I had been dating the same type of guy all my life.
He was a white guy who played baseball, lacrosse or a guitar — all equally mediocre. He had an older brother who gave him his first joint and a family who really loved sailing — I mean, like, a lot. He had a blue-collar job despite being from a middle-class household, and he quoted Caddyshack way too much. It was the same guy, over and over — no variety. I could take any one of them home to meet my family, who would have been ecstatic to welcome “the son they never had” into our lives, readily.
I had convinced myself I would be married by the age of 30 to a man I’d been dating for two years and two months (since that is the allotted time study after study has shown is linked to a happy marriage). This meant I only had three years to find him, leaving me very little time to sample the dating goods. There were so many other types of men — and women — in the world that I wondered if there was someone else out there for me. Perhaps some unconventional type of relationship I hadn’t yet considered was waiting.
I vowed that I would take the year to date completely out of my comfort zone, and by the next Valentine’s Day, be having dinner with someone who would be more exciting and maybe even a bit dangerous.
The 46-year-old father of two
In a large corner office at one of the many freelance jobs I worked in my twenties sat the 46-year-old owner of a clothing company. He was messaging his daughter on AOL, like we did back then. She was a year younger than I was, which crossed my mind when I decided to go in and flirt with him. I knew he had just separated from his wife, since he had been looking for apartments in Tribeca. He asked about the neighborhood, as I was from New York and he was not.
I offered to give him a tour and suggested we start at a small romantic restaurant in the vicinity of his potential new home. At dinner, I made it clear I was interested in him by doing something incredibly immature, like eating a strawberry seductively or touting one of those embarrassingly corny moves that at 24 you do not yet think are cheesy. It worked. We dated for about two months, but I cut it off when he started buying me things you’d buy your kid and not your lover — gross. Too creepy. He was not going to be in the picture by June, let alone February.
The famous actor
There was a bar on my block where celebrities hung out. Whenever you picked up a copy of Us Weekly and there were photos of “disaster starlet A” seen canoodeling with “bad boy actor B,” it was at this bar. I was taking a friend there for dinner, and I was seated in the eye line of a very well known actor I will call Mr. S.” At the time, Mr. S was starring in the highest-rated TV show of the ’90s. I met his gaze twice but looked away quickly so he didn’t think I cared that he was there.
When my friend went to the bathroom, Mr. S slid into her chair and arrogantly asked, “Were you staring at me?” I said no and acted appalled that he would invade my privacy. He said, “You’re hot. I’d love to take you out, but I’m going to L.A. for two months. Can I call you when I get back?” I gave him my number and chalked it up to a drunken celebrity encounter — but he actually called two days later.
Our first date was a hip-hop show we watched from backstage and a party that lasted into the morning. We dated off and on throughout the summer, but I found him terribly insecure and dumped him in August. I would have ended things sooner, but he was famous. What can I say — I was young.
Jeffy the Giant
When you’re a petite thing like me (5’2), you are painfully aware of what you look like dating anyone taller than six feet, which is why I decided to aggressively pursue the guy on the treadmill next to me. His name was Jeff, he was 6’7, and he was my next target. Poor Jeff didn’t stand a chance, as I had a litany of self-help books on my side. I had read several (it was the ’90s, we all did) and Why We Love: The Nature and Chemistry of Romantic Love suggested attracting men using sexual imprinting, sorta like birds do. It worked, so I bought some six-inch heels and climbed up Jeff as often as I could, which kept things going well into December. That’s when I met Michelle.
Jeffy the Giant traveled for work, and while he was away I became close with his friend Michelle. It was the first time I heard the term gender fluid, which is how Michelle identified herself. She was with Laura for three years, Tom for two, and now she was single.
I had never been attracted to women and had always identified as straight, but if this was my year of dating dangerously, I had to try it all. Michelle invited me to her parents’ house in Sag Harbor, just the two of us. On our last night, we drank quite a bit, and I moved closer to her and asked if we should “fool around.” She laughed at me and said, “You are so straight.” “Is that a no?” “That’s a no.”
The perspective changer
I was one of those twentysomethings you would have hated. I was really into the gym, men, fashion and nothing else. I had only dated men with zero body fat and had never considered a heavier lover, but when I met Zack, his crystal blue eyes, utter charm and coolness obscured his size. I fell hard for him in January and couldn’t wait to introduce him to my self-absorbed, vain friends and to spend Valentine’s Day with him. My friends would see that personality and charm ruled out over any superficial ideas they held about men, and it would be true growth on their part. Unfortunately, I didn’t get the chance to do that. Zack dumped me February 10 for a gorgeous blond leg model who understood that lesson sooner than I did.
My gay friend John took me out to dinner for Valentine’s Day. He, too, was single. He complained that, like me, he had been terrible at choosing men. I told him to go on an adventure and start dating out of his comfort zone. While it didn’t work for me quite as I expected that year, it did have long-lasting results. The man I eventually married (after dating for two years and two months) was not a white guy, and his parents hated sailing, but he did play both baseball and a guitar. Some habits die hard.