IT HAPPENED TO ME: I Hired A Dating Coach

In a moment of frustration and loneliness, I Googled dating help.

Apr 3, 2014 at 11:00am | Leave a comment

A year ago, I was a single 30-year-old woman who felt lost in my generation’s world of courtship. None of the men I knew were asking women out in person. The online dating world felt foreign and manufactured, where time spent in the game of messaging and telephone robbed us of the opportunity to meet-cute at the grocery store.
 
In a moment of frustration and loneliness, I Googled dating help. I found the website of a dating coach. Her headlines targeted my insecurities: “Do you have a dateless calendar?” and “Are you having difficulty meeting men?” Yes, I thought, aren’t we all?  
 
Her clients spoke warmly about her ability to match them up with compatible partners. Perhaps she had a gift for helping people through this, I thought.
 
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Me on the precipice of understanding men.

 
I made an introductory phone consultation with the coach to talk about her services.  She called me on my cell phone and quizzed me to assess my commitment to love (How long since my last relationship? What’s my type? Why did I think I was single?). I told her that I didn’t prioritize meeting men given my work schedule and that it had been over a year since my last boyfriend. I asked her if there was anything she sensed that was holding me back. She said no, I sounded quite open to love and she would be happy to work with me. She asked me to read a few select dating books before our next talk. 
 
I tackled my pre­-meeting homework on a work trip to Michigan. Her books suggested behaviors that kept women from meeting the right men: impossible standards, asking men out, getting too physical too quickly and still harboring feelings for an ex. I noticed that many of my friends who had displayed those “man repelling” behaviors while dating were now married. What was different about the women who were just able to live their life and bump into "the one?"
 
The next week I met the dating coach in person. She was soft and feminine like a designer hand cream. She reminded me of the girls from my sorority days, who mastered the art of making a man feel desired. They always seemed to get the guy but were unhappy once they got him, finding that he lacked long-term boyfriend skills.
 
The coach started our session by asking me to talk to her as if we were on a date. My friends and co-workers adore me for my witty repartee but sitting on this woman’s couch, I froze. What followed was a highlight reel of my worst conversation foibles. I gesticulated wildly, stammered about uninteresting topics and kept losing my train of thought. She nodded her head and said, “Well, now it's time for you to give me a compliment.” It was unclear if she was still in character or if the coach herself wanted me to tell her something nice.
 
I fumbled for something to say that was genuine and noted that her earrings were beautiful. She looked at me sternly and declared that men really appreciate compliments on a first date. I confessed that giving someone a compliment didn’t come easily to me. She wrote down “compliments” on a yellow sticky note she gave to me and told me to come back next time with a completed online dating profile. 
 
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Holding a dog instead of looking sexy.

 
I met with the coach the next week to show her my profile. She looked through my profile photos and assessed, “You’ve got that girl next door thing going on but you don’t have any sexy pictures; guys need to know you will enjoy sex.” I told her I didn’t really have any come hither photos and she said I needed to find one.
 
She showed me an example from one of her other clients who was holding her hair seductively over her eyes, “Guys see this and know that she’ll be good in the bedroom.”
 
Then she read my profile and said, “You’re funny, you’re really funny.” I told her I was a part time writer. She said that was good because men want a woman who can have fun but that I also needed to appear vulnerable. She told me to add to my profile that, “Even though I appear to have it all figured out, I’m secretly hoping to find someone who can help me navigate life.” I laughed and said that made me sound like I was looking for a captain.
 
She went into my online dating inbox and started drafting messages on my behalf to men she found attractive. They were men with pretty faces whose profiles were short on humor and quirkiness. Her messages were bolder and more flirtatious than I would have put together and were full of grammatical errors. She told me that she’d check in on me during the week to see if they’d call.
 
All the men she messaged were eager in their replies back to me. One of them asked for my phone number and said, “Your message made me want to stop everything and call.” I couldn’t deny that her coquettish approach worked but I felt like a liar, wooing men with her identity. One of the men called me on my cell phone and his voice reminded me of men from my grandfather’s generation. He fired off a list of questions about my personal habits and told me we’d be great together because I loved to grill seafood and go to the gym. I cringed when he told me he’d call me soon to set up a date.
 
I wondered if I was getting schooled in the art of first impressions, to the detriment of listening to my own intuition about men. I hadn’t heard from my dating coach, so I set up a follow­-up appointment to talk to her.
 
The next week when I arrived at her house she was pacing her hallway and talking on the phone. I sat in her lobby reading women’s magazines while I overheard words like “television” and “producer” on the other end of the line. When our session began later, she told me she was sorry she was late but there was good news, she was asked to be a guest host on a TV show about dating. She seemed too excited about the opportunity to focus on our agenda.
 
I told her that all the men had gotten back to me but in truth I was hesitant to meet them. She said I needed to give them a try and confessed she had been on over 100 first dates with men she’d met online before she met her husband. I told her that sounded exhausting and asked what she learned from her experience.
 
She said, in a tone that suggested she was handing me a secret “Men don’t like it when a woman talks about something but doesn’t follow through with action.” It struck me as fortune cookie wisdom and it reminded me how she had frequently told me that she would check in on me but failed to follow through.
 
The coach canceled and rescheduled our appointments over the next few weeks and I grew resentful of having to chase after her. If she were a suitor, she would have instructed me to move on by now. The man who grilled me about my personal habits finally called to set up a date. He sounded aggressive and controlling on the phone. Talking to him felt like I was a dead body getting dragged through mud. I accepted his date but canceled the next day.  
 
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I still haven't found what I'm looking for.

 
In the coming weeks, the dating coach still hadn’t followed up with me, even though we had two sessions left. I briefly considered making another appointment, but stopped. I had to admit to myself that this wasn't working for me. There was a wide gulf between the league of women who had a full dance card and me, for whom endless dates felt like a chore. I learned that I had sought her out on a fool's errand and that she didn’t hold the secret formula to love. In truth, no one does. Despite all evidence to the contrary, I began to trust that I could meet the right man all on my own.