Are You too Picky or Not Picky Enough in Dating?

Posted by in communication skills in dating, dating after divorce, dating in midlife, first date success | 0 comments

not picky enough“You’re too picky”, says your mother. “You’re not picky enough”, says your best friend. Which one is it? A few years ago, a thirty-year-old woman came to see me. She had been on 200 dates and was wondering if she was just too picky in dating. She was about to board a bus and travel 4 hours to meet a man for a third date, someone with whom she felt very little connection and zero attraction. “Why are you getting on that bus?” I asked. “It sounds like you are not at all interested in this man. He bores you. You’re not attracted at all. Why waste precious time and money on a guy with no potential? It’s not too late to cancel.” “I’m not sure what to do,” she answered. “That’s why I’m here to see you. My family thinks I’m too picky.” “From what you’ve shared, I think you’re probably not picky enough,” I said.

Are you too picky or not picky enough in dating?

You’re not picky enough if…

  • You’re dating every man who contacts you online
  • You’re dating every man you’re fixed up with before vetting them
  • You’re dating every man who asks for your number
  • You go on second and third dates with men who turn you off and don’t have any of your “must-haves”

You’re too picky if…

  • You only date men who are 6 feet tall and above
  • You’re looking for instant chemistry and won’t date a man twice if you don’t feel immediate attraction
  • You only date men with advanced degrees
  • You only date men who earn seven figures

Notice a pattern? I want you to look beyond the externals and focus on the heart of a man. I want you to see a man for who he’s become, not who he was in his last marriage or relationship. I want you to be open to men who make you FEEL safe, cherished, heard, and seen. Not men who make you feel nervous, unsure, and ignored.

Nice men are lovely, but if you’re falling asleep on your date, nice is not enough. You want a good man with a good heart and soul. You are seeking a man with a steel core of integrity, not a Ph.D. or a million dollars salary.

The short essay below illustrates why it’s so important to see beyond the exterior of a person.

The Myth of You and Me

by Leah Stewart

A person is not a suitcase, with a finite number of items to unpack. A person is a world. Look at any photograph – of a stranger, your father, your very best friend. Sometimes the mystery is all you see. I have always been partial to the in-between, the blurred highway outside the window, that suspended time when everything you were lies behind you like a molted skin, and everything you might become shimmers at the horizon. You might choose anything and make it happen, constrained by nothing but your own imagination, sure that not even gravity can hold you.

When you meet a new person, all you usually see is the tip of the iceberg. There’s a whole world that lies beneath the surface. And men at this age have a history. So do you. You wouldn’t want someone to judge you based only on what you look like or what you do for a living, would you?

So, next time you meet a man, take a peak at what’s underneath. Find out why he chose his profession and what he loves about the work he does. Discover what he’s passionate about, what makes his heart sing; the music and art that move him, the places he’s visited that made a lasting impression. Find out the “whys”, not the “whats”. It’s much more important to know what he learned from his past relationships than who initiated the divorce.

What questions will you ask on your next date so you can discover if you’re a good match?

*photo courtesy of





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