The shy one, the hottie, and the picky one: NYC women talk about love and dating

Recently I paid a visit to New York City and got together with some of my readers at the Hudson Hotel for a little chat. A fundraiser by mayoral candidate Bill DeBlasio had taken over the main bar, so we found a bench in the Hudson Common eating area and got down to discussing love, happiness, and guys.

I like these get-togethers because of how much I learn from hearing the stories of real, live readers. A book by its nature is a one-size-hopes-to-fit-all device. But in person you, my readers, are all different shapes, ages and races, with diverging concerns. Here’s a sampling of what I heard.

Marci, the shy one

Take Marci, for example. She said that her issue was that she always ended up being one of the guys. How could she make things take a more romantic turn when she didn’t want to be just friends with a guy?

At the same time, Clara sitting right next to her had the exact opposite problem. Guys just wanted to hook up with her, and she just couldn’t sort out the good guys from the players.

And now that I could see them and hear them, I had more information with which to diagnose what the hey was going on.

Marci’s about 30. By her own admission, she’s shy. She’s wearing an elegant and conservative outfit that covers everything up. She’s tall and big-framed, with an open and friendly smile, so you wouldn’t peg her as being shy. As she speaks, you get a sense that her preferred mode of discourse is friendly formality.

So why does Marci consistently fall into the friend zone? Because when you’re friendly and formal with people, you’re going to be formal friends with them, not a romantic interest.

So how do you get out of the friend zone and into the romance zone? Simple: get flirty.

Up to now, everything about Marci has been proper, linear, safe. The problem is that proper, linear and safe has inspired no man to declare his undying love for a woman. What you need is a little more of the flirty, curvy and dangerous. The idea is to provoke emotion and thought in the man’s body and mind. Every woman has the means to do that.

In the case of Marci, there are some potential fixes:

1) Engage in “curvy” conversation. Everyone knows where linear conversation goes: “How’s the weather? How was work? Is your pet better?” Linear = booooring. Ain’t gonna get you anywhere.

On the other hand, nobody knows where curvy conversation goes. “So, you seeing anyone? Why not, is something wrong with you?” If you deliver that with a smile, a guy will have no idea what you’re up to. Are you giving him a hard time? Are you interested in him? Do you want to set him up with someone? Are you just entertaining yourself?

Suddenly, conversation with you has become more interesting, because he’s not quite sure what you’re going to come up with next. And because he’s not sure of your intentions, now he’s thinking about you when you’re not around.

Here’s a secret: when a guy thinks about you when you’re not around, this encodes in his brain as “I must like this girl.” In one smooth move, you have taken residence in the romantic quarter of his brain – or at least romantic-adjacent. Friend zone begone.

The essence of flirting is a little bit of unpredictability and danger. Curvy conversation accomplishes that.

2) Show a little more skin. If you want to get out of the friend zone, you want to do things that evoke an emotional response in a guy. One thing that does that is to put to use what your mama gave you and show some skin.

How much skin is the right amount? Somewhere between Sexy Pirate Nurse Slut Ho Halloween outfit and a burqa, there is a balance. And I read somewhere that that balance is 40%, so we’re going to call this the 40% rule henceforth.

How do you get to 40%? Simple: use the Rule of Nines, one of the things I remember from medical school:

  • Head: 9% of body surface area
  • Front of torso: 18%
  • Back of torso: 18%
  • Each leg: 18%
  • Each arm: 9%
  • Crotch: 1%
  • Total body surface area = 9 + 18 + 18 + 36 + 18 + 1 = 100%

So if you expose half of your legs below the knees (18%) and all of your arms (18%), with your face (4%) you’re showing 40% skin. If you’re wearing a backless floor-length dress (18%) with bare arms, that’s also about 40%. To project less sexual energy, show less than 40%. To go on the warpath, go over 40%.

Clara gets too much attention from the wrong guys

So Marci needed to get out of her comfort zone and be a little more flirty. Clara, on the other hand, had no issues with the flirty part. She’s 23, short, petite, and wearing a slinky black dress which shows a distracting amount of décolletage (also known as “cleavage”). It’s easy to understand how a lot of guys would be interested in hooking up with her.

From the outside, this may seem like a high-quality problem: “Oh, boohoo, poor thing, she’s got sooo many guys who are into her.” But a high-quality problem is still a problem. And I’m guessing there’s something not entirely savory about every guy you meet trying to get into your pants. It will probably make you feel objectified and distrustful of men, perhaps shutting you down to their advances. No wonder there are so many really attractive women who remain perennially single.

Luckily, there is a solution. The way men respond to you has a lot to do with the way you present yourself (see Marci’s case above). Here are some things Clara can do.

1) Dress more conservatively. I understand that women like to look hot, so they get all decked out in 7-inch Jimmy Choo stiletto murder heels, super-slinky dress and blood-red lipstick, ready to slay all oncomers.

Well, let me tell you this: it’s not fun being slain. And if you look too hot (there is such a thing), the primary emotion that most men feel around you is FEAR. That’s right: adrenaline kicks in, and what we feel is flight-or-fight. And we become too scared to approach you.

But there is a subset of guys who are not scared off: players. They see you as a prize, as a challenge, as a contest to be won. And they will approach you. And all the nice guys will stay away.

In one move, you managed to attract all the jerks and alienate all the nice guys. Nice work. And you wonder why all the guys you meet just want to hook up with you.

So if you’re already a smoking hottie-pie, tone it down a little. Wear something less provocative, more conservative. Don’t let the floodlight of your sexiness blind the men to all the great qualities of character that you’ve worked so hard to cultivate. That way, something like your soul has a chance to come through. Which brings us to…

2) Talk to him. If you want to sort for the good guys, you must talk to him. This is how you find out how intelligent he is, how empathetic he is, and what his true intentions are. Drink alcohol only sparingly and gather in a place where you can hear him speak, because this is when you’re gathering critical information about this stranger who might become the father of your children. Liberally ask the magic question, “What’s important to you about that?”, and listen closely as he shares the innermost contents of his soul with you.

This is also a chance for you to show him that you’ve got a great mind to go with the hot legs. Conversation is the broadband communication system of the human brain, so use it to your advantage to glean and convey important information about your suitability for one another.

3) Give him a chance. Clara happened to be there with her 21-year old sister, Sara, also single. Both being so young, good-looking, smart and sweet, I wonder if there was something going on invisible to the naked eye that was keeping them from finding a good love match.

There was: Clara and Sara were both vetoing each other’s dates: “Oh, he’s just not good enough for you.” Well, guess what: if you’re her sister and have known her your whole life and will lay your life down for her, in your book there is no man alive who is good enough for her. Get over it and unless the guys are unemployed and torture baby hamsters for fun, give the poor suckers a chance. And your sister, too. You do want to be an auntie someday, right?

We are super-susceptible to the opinions of our intimate friends. If one of them says, “Oh, she’s not so pretty” about a woman I like, I can feel my interest instantly dropping a few notches. So it behooves Clara and Sara to refrain from saying mean things about their respective suitors and to stop sabotaging each other’s love lives.

There’s something slightly sinister about this, too: unconsciously, the sisters are aware that if the other one finds a guy, that means less time spent with her. So yes, it’s very likely that a friend of yours – the one you’re closest to and has the most to lose – has actively sabotaged your interest in a guy in the name of “protecting” you. And she will do it again.

So if you’re serious about having a relationship with a guy, you need to tell her to knock it off. If a unified chorus of friends tells you a guy is toxic, fine – you should listen. But if it’s one friend who’s consistently pulling you away or poisoning things early on, there just may be ulterior motives at work here.

Polish girl seeks Indian guy – but why?

Then there was Patricia, the fiercely intelligent, driven Polish transplant. Her question was about intercultural relationships. Specifically, she found herself attracted to Indian and Pakistani men. However, she wasn’t quite sure how to deal with their traditional mindsets, especially when the parents insisted on a bride within their own ethnicity.

I’m all for intercultural relationships, but the Polish-Indian axis didn’t make a lot of sense to me. I mean, her true fulfillment depended on just that particular 1% sliver of the population? So I had to ask her: “What’s in it for you, Patricia?” After a while I got a sense that Agatha thrives on challenge: moving to the US; solving difficult problems; taking up a difficult dance style (tango, in this case); and maybe choosing boyfriends with difficult families who wouldn’t let her marry him.

Remember that fulfillment is not a person, but a set of feelings. Was breaking through the challenge of swaying an Indian guy to marry her over the objections of his parents Patricia’s real fulfillment, or just another habit? Was she in it for the prize or for the joy? I wasn’t familiar with the full back story, but as far as I can tell, there are plenty of guys from all ethnicities out there who could catalyze Patricia’s growth and fulfillment. Especially in a place like New York City, where there are literally millions of interesting folks from all over the world. Perhaps it was time for her to focus on the substance of real companionship and emotional connection rather than an insistence on a particular symbol, of which ethnicity is one.

Thanks for the ladies who braved the wilds of Manhattan and managed to find me at the Hudson that night. Now that I know how much fun live events are, I’ll be having more of them here in San Francisco and also when I travel. In the comments below, let me know where you abide, and if you can put together a group of 20 or more women, I’ll see what I can do to come visit.

4 Comments on “The shy one, the hottie, and the picky one: NYC women talk about love and dating”

  1. Brenda

    This is gonna be fun! One thing I started doing was flirting with the door guy in SOHO where I hang out as soon as I got there. He gave me some information, got to be my hero and I was in the mood the flirt and socialize! I met I guy that emailed me and told me he was enamored with me as soon as we met and wanted to kiss me but held it back. Now we’re talking through email. I hope he asks me out soon!

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