Why a crappy date with a man with a comb-over is the best thing that could happen to my love life

Over the past year I’ve been totally single. Aside from a few short romances, I’ve been in solid dating mode — I’ve probably gone out with 20 or more men, and I was very proud to say that not a single one was a bad date.

My secret? Expectations. All I wanted to do was go out, have fun, meet interesting people and feel attractive. Guess what? Totally easy! One guy after the next was cute, smart, sweet and charming. Some of them were also hot and I enjoyed their company in special ways. Anyone who would listen had to hear me go on about all the good times I was having — a favorite subject of this site where I wrote ad nauseum about why single moms should jump into dating and lavish in its riches.

But I know how life is and I know myself — and I knew that was a phase that would run its course. A couple months ago I started to feel a shift — a call for something more. I realized that all that fun dating was important — after all, I learned so much about myself, what I’m looking for in a man, and dating satisfied my needs as an adult woman: to feel attractive, for companionship and the company of men. But all this gallivanting has its time and place. Sitting accross from a one hospital administrator — malbec and skirt stakes between us — stunned by his tales of fighting an ex for the right to medicate their 7-year-old for ADHD even though she scored 98% on all academic tests “because I want her to achieve at her highest level” — I knew it was for a time for change. Suddenly I felt in my gut, my bones (and other places, too): Now I want to find someone to love. Someone who loves me and loves my kids and wants to create a family with me.

Right around the time, I connected with dating coach Kavita J. Patel. Our reason for meeting was professional — she is a wildly successful relationship and dating coach, and she generously allowed me to pick her business brain. She also offered me a coaching session.

Now, I know a few dating coaches, and I know people who are really smart about relationships. I’ve been to my share of therapy over the years. Lots of people have helped me figure out my crap. But Kavita blew me away, right from the get-go. “I want you to know that I read your answers to the questionnaire you filled out,” she said when we started our call. “But I might ask you the same questions again. I get an intuitive hit when I hear things said out loud.”

I liked where this was going already!

I gave her a quick rundown of my recent history, including my pat, enthusiastic reports of my year of power dating. “Wow, that is so great to hear!” Kavita said. “I very rarely hear women say they enjoy dating.” My chest puffed up with pride as I chatted on my iPhone from my home office.

I explained that I could feel myself growing restless with all my fun, casual dates, and felt the need for a serious, long-term partner. Where do I start?

Kavita’s specialty is helping you get to root of your dating issues by examining your own family history. She stunned me by the accuracy of her assessment as she immediately dug into mine — straight to issues that are so old and painful I won’t write about them here. But I will share this: She asked about my mom, and her relationship with men. I explained that my parents divorced when I was very young, and aside from some dating, my mother never had a serious relationship. Her messages to me about men have been mostly negative.

“You’re attracting a lot of fun people, but as soon as it seems like it could get serious, you get scared,” Kavita intuited. “I want you to ackmnowedge how afraid you are of meeting someone who would fall for you and your kids, because you are afraid that if they do, and they become part of your family, they may leave and you’d all get hurt.”

Um, ouch. So true.

“I also see you rebelling against your mom — it’s as if you want to prove her wrong about men by being so positive about them.”

Um, ouch times 10!

When Kavita works with clients she always gives them “love work” — homework assignments to help you sort out your inner self so you can move forward with finding what you want in love. Her assignment to me was to ask my mom to describe her own experience with men that created her attitudes. “But my mom and I have a contentious relationship,” I protested. “My mom isn’t well now — I can’t do this. Don’t make me!”

Kavita was firm: “You have to go to her as a child asking for help from her mother. Tell her you need her help so you can move on to the relationship you want. If you ask from a place of vulnerability, I guarantee that she will help you.”

I stalled for a few weeks. Every time I talked to my mom on the phone, I thought about asking her all those questions, but I got scared. Scared of an arguement. Scared of what I might hear. Scared that I might actual experience some healing within myself which could lead me to the very scary place of being involved with a man in a real way.

And then one Tuesday morning after checking my OKCupid account for the millionth time and once again feeling disappointed that a perfect man had not messaged me, I called my mommy. I explained my mission and I asked questions. She talked. I listened. I heard stories I had not heard. I heard stories I’ve heard a million times — but I heard them through new ears. I thought of Kavita’s words: “When you learn about your mom’s attitudes about men, you will have compassion for her, and that will break the cycle you’re in.”

Indeed, my cycle has been broken.

My past few dates have been less about laughs and sexual innuendo over tapas, but rather me searching for words upon hearing: “You know what? I’m not really into kids — I want a dog!” or, “I’ve never lived anywhere more than 3 years — I’m a total nomad,”  or “I’m so glad my kids are now off on their own — been there, done that!” There have been other deal-breakers too — like the comb-over, for example.

I welcome all these not-so-great experiences, as painful as they may be (seriously — just clip your hair short, OK? A confident bald man is sexy!). After all, anyone can party through life, but that eventually results in hangovers and trips to Betty Ford. Instead, I find myself calming down, digging into what I really want and what would work for me and my kids in the long-term. It’s hard and it’s lonely — but it is important.

After my session with Kavita, my mind was kind of blown. “Thank you,” I emailed her. “You just busted through 36 years of my BS in 45 minutes. You have a gift.”




Check out Kavita’s FREE 3-part “Love Training” videos. Today’s subject: When should you sleep with him? (Answer: First date might be OK! Don’t you love her?!)



Emma Johnson

Emma Johnson is a veteran money journalist, noted blogger, bestselling author and an host of the award-winning podcast, Like a Mother with Emma Johnson. A former Associated Press Financial Wire reporter and MSN Money columnist, Emma has written for the New York Times, Wall Street Journal, Forbes, Glamour, Oprah.com, U.S. News, Parenting, USA Today and others. Her #1 bestseller, The Kickass Single Mom (Penguin), was named to the New York Post’s ‘Must Read” list.

Emma regularly comments on issues of modern families, gender equality, divorce, sex and motherhood for outlets like CNN, Headline News, New York Times, Wall Street Journal, Fox & Friends, CNBC, NPR, TIME, MONEY, O, The Oprah Magazine and The Doctors. She was named Parents magazine’s “Best of the Web,” “Top 15 Personal Finance Podcasts” by U.S. News, and a “Most Eligible New Yorker” by New York Observer.

A popular speaker, Emma presented at the United Nations Summit for Gender Equality. Read more about Emma here.

9 thoughts on “Why a crappy date with a man with a comb-over is the best thing that could happen to my love life

  1. Yes, all stages eventually come to an end and then it’s time to open up and ask for what we really want.

    It will be great to see you break free of your limiting beliefs and become “Wealthy Remarried Mommy!” :)

  2. Hi Emma, I feel what you are going through, thank you! It’s great to hear what women feel and think and it makes me more aware. Thanks again, Richard.

    1. The guy that you responded to is a psychopath. He is trolling your sight to get into what women feel and think so he can manipulate them. He can’t empathize and has to learn it from others not to mention finding a single wealthy mommy. I would be careful.

      He didn’t ‘go through’ anything.

    1. @Jennifer – coaching sessions are not for the faint of heart, that is sure. But I recommend her totally – Kavita is one part intuit / one part therapist.

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