I first read the Craigslist ad six years ago. I had graduated from college about a month before, moved to New York with few practical connections and was desperately looking for work. The ad asked, “Are you cheerful? Outgoing? Comfortable talking to members of the opposite sex? Apply to New York Dating Coach!”
I was all of those things! But I was also fairly sure that this sort of come-on was how 22-year-old liberal arts graduates were lured into prostitution rings. So I — cleverly — responded to the ad stating that while I definitely met the criteria I was not interested in sex work, which was not to say that I did not have a lot of respect for people who embraced different lifestyles.
I received a call back from the head of New York Dating Coach, Art Malov, who laughed and explained that the dating coaching service was definitely not a prostitution ring. However, I would be expected to go on “mock dates.” The clients — mostly male, although some are female — are adults of all ages and professions looking to become better daters. Art and other coaches help show them what to wear, how to set up appealing online dating profiles, accompany them out to nightclubs and bars and help them rehearse a coffee date with a girl.
That’s where I came in.
So in exchange for $40 per session — mock dates run about half an hour — I agreed to sit and have coffee with a client who is told to behave as though he’s on a first date with me. Art sits at the next table and takes notes on what the client does right or wrong. Art and I confer about things I really liked or really didn’t like afterward — outside the coffeeshop, so the client doesn’t listen in — and then he discusses my impressions and his notes with the client afterward.
Since I’ve started this job six years ago, I’ve gone on approximately 300 mock dates. They range from inexperienced college students to widowers trying to meet new people. A significant number are from foreign countries, and are hoping to familiarize themselves with American customs. Some are pressured to enlist an expert by their parents, who pay for the dating coach. Others simply have a more practical, New York approach — why not hire an expert to teach them how to date better? Almost all are looking for long-term relationships.
My main goal is just to make sure the person has fun. I hope that my being there makes them realize that sitting across from a stranger at a table doesn’t have to be scary, even though having someone nearby taking notes on what you’re doing must be really stressful.
It’s amazing how much I’ve enjoyed most of these mock dates. I’ve learned from clients what it was like growing up in Iceland and the best places to check out if I want to try skydiving, and I’ve absorbed countless great restaurant, book and TV recommendations.
That said, it’s amazing to me that in a city where men and women interact all the time — and seem to be having the time of their lives — that some guys still get fundamental stuff wrong. Here are my worst dates over the years — and the valuable lessons NYC men can learn from them:
The guy with opinions very few people share
Two years ago, I met with a 30-something guy for coffee. There was nothing unusual about him. He was clean-cut, wore a T-shirt and jeans and had sandy brown hair. Like most mock dates, he was a little nervous and searched for a topic of conversation.
We chatted pleasantly about whether he had any trouble finding the coffee shop, and whether he was looking forward to the weekend. I mentioned that fall is always my favorite season in New York. The guy asked me if I remembered what happened to the Twin Towers on Sept. 11. I said, yes, of course I did, and that it was tragic, and that I imagined we’d probably think of that every September forever. I was already thinking, “Well, gosh, this is a really sad way to start a date, but maybe he was a first responder in which case he’s a hero and . . .” Then he leaned in and whispered, “You know the CIA did it.”
My mouth dropped. How could I possibly respond to such a statement? Thankfully, I didn’t have to, as Art called the session to a halt immediately.
The Lesson: Even if your opinions are less controversial, unless you’ve met someplace where you know that the other person will agree with you (like a CIA conspiracy chat room), keep the conversation fairly light on the first date. It might seem archaic, but not discussing religion or politics right away is still a good idea.
The “nice” guy
When I first started out six years ago, I met with a 25-year-old guy whose Axe body spray made him smell like a frat-house laundry room. He swaggered over, sat down with his legs spread and immediately slapped the table like a crazy person’s high-five.
He then stared at me intently and said, “Why won’t women date nice guys?”
I told him that women actually do want to date nice guys, but they don’t want to date guys who are pretending to be nice in exchange for sex.
I also couldn’t help but feel relieved that I have genuinely kind male friends, who aren’t just listening to women because they think it will lead to sex — and who have no trouble getting laid.
The Lesson: The nicest people I know don’t usually feel a strong need to self-identify as such, and it’s a huge turn-off when anyone has decided that they’re owed dates for any reason. Women are going to date people they have personality traits in common with, and who engage them, and who make them feel like the coolest version of themselves.
Do whatever fits your personal definition of what a “nice” person does. Mentor a kid. Find a charity. Maybe it won’t make women jump into bed with you immediately, but I bet it will make you more attractive to the opposite sex overall, because you’ll feel better about yourself, be proud of the good things you do, acquire a wider social circle and have interesting stories to tell.
The guy who wants his ex back
About three years ago, I met with a man in his 50s. He had a stocky build, salt-and-pepper hair and a receding hairline. As soon as he sat down, he informed me that he was in the process of a separation.
I thought perhaps he was telling me this as part of some moral obligation. But it turned out he just really wanted to talk about his estranged wife, whom he clearly still loved very much.
“So, let’s say you run marathons,” he speculated.
“I do not run marathons,” I replied, a bit confused. “But I do pilates and yoga, and I play some tennis.”
“My wife runs marathons,” he insisted. “So if I were to ask you how your marathon was going . . .”
It was then that I understood what was going on. He wanted me to pretend I was his ex so that he could figure out how to act in order to get her back.
“The marathon is going great,” I responded. “I think I’m going to win!”
The Lesson: If you are seriously hung up on your ex and can’t think about dating anybody else, or dating in general, you need to be with a therapist talking through your feelings. Or, I really hope, because I think he’ll really, really pay attention to her marathons going forward, a couples counselor.
The sad guy
“So, what do you do?” I asked.
A sad look streaked across his face.
“Oh, I do tech stuff,” he replied. “It’s boring.”
It was my first mock date. He was in his late 20s, and we were sitting on a bench in Central Park on a lovely summer day.
Despite the glorious weather, his head hung down and his shoulders slumped.
“Oh, it can’t be that boring,” I replied, desperately hoping that he was secretly passionate about his work, and just thought I’d be bored by it. “How did you get into it?”
“No, really, I hate my job. Let’s talk about anything else.”
So I told him about all the exciting things I was hoping to do now that I was living in New York.
That was when he told me “not to get my hopes up.”
I felt incredibly sorry for him — he was resigned to unhappiness, and that’s not something people find attractive.
The Lesson: If you do hate your job, well, first of all, it would be great if you were trying to change your job. Talk about what that transition is like — people respect people who refuse to be unhappy. Or make sure you talk about things that do make you happy. If you’re miserable 40 hours a week, it’s nice to know that you’re getting great pleasure cooking or being in a band or going to ballgames in your spare time.
The oversharers
Back in 2009, I went out on a mock date with a tall, good-looking finance dude. He was preppy, blond and Kennedy-esque. He came off as arrogant, but in a sexy way.
My first thought was, “What is he doing here?”
Then he spoke.
“So, me and the bros from my fund — do you know what a fund is? No? It’s complicated, don’t worry about it.”
I did know what a hedge fund was, but he clearly wasn’t interested in my witty banter about Warren Buffett.
Instead, he launched into a “hilarious” story about a recent trip to Thailand, in which he and his pals engaged in the sex trade on the company dime.
The punch line?
“I bought a hooker — and she turned out to be a transvestite!”
Maybe I would find that a hilarious joke under different circumstances, but I do not live in hell.
Then there was the date, about a year ago, with a very sweet man in his early 40s. He had really put effort into his appearance in a way that I admired — he wore cool glasses, and had chosen a very classic cashmere sweater.
Things were going really well until about halfway through the date, when he offhandedly mentioned his struggle with constipation.
“Sometimes we all have troubles with constipation,” I helpfully responded.
That launched a conversation about the miracle of prune juice.
For the rest of the date, I kept wondering if he should maybe just go to the bathroom and hang out there with a magazine.
The Lesson: First dates should be a time to get to know each other, but they should also be light, and breezy, and hopefully funny in a nice way. Do not mention anything you’ve done that could be considered illegal or immoral until you have a better understanding of how another person would feel about that, and that can be kind of sussed out after a few dates. And don’t mention bodily functions of any kind. Especially in the first 15 minutes.