Dating Coach Diary: My First Experience as a Dating Coach

I was broke, single, and on the verge of dropping out of Columbia University when a friend suggested that I become a dating coach. The idea seemed insane, “Why would anyone pay me to do this?” My first kiss was with the girl I took to prom, and I didn’t lose my virginity until age 22.

Yet after years of intensive study of human behavior and a lot of trial and error, I had evolved into a ladies man, at least in the eyes of my friends, and the go-to person for dating advice. I decided to take my friend’s recommendation and give a career as a dating coach a try.

I posted an ad in the “women seeking men” section of Craigslist, “Learn the art of meeting and attracting women, guaranteed or money back.” I figured that at least some of the guys in that section were looking for prostitutes, and if they would pay them, then they would pay for my help with meeting women. What I didn’t expect was how the ad would almost turn me into a prostitute… I’ll soon explain.

The first person to respond was Jason. After a phone conversation, we agreed to meet at Starbucks, a block from a cluster of bars in Manhattan’s Lower East Side. Jason was a 24 year-old Asian-American accountant. He was good looking, with dark hair, skin, and eyes. He wore thin framed glasses that gave an impression of confident intelligence, yet he was shy. He told me that he wanted a girlfriend and had tried speed dating, singles websites, and books by dating gurus. He was frustrated and open to trying something different.

In our first meeting, I covered everything I knew about women, dating and relationships. I talked for so long that the Starbucks manager kicked us out to close the store for the night.

I recommended that we go practice approaching women at one of the bars on Ludlow Street. Jason, like many men, had an innate fear of approaching women. He was scared of rejection, enough so that the suggestion made his body tense and his voice shiver. Only through my persistence did he agree to give it a shot.

I led Jason into a dark street corner about a block from our destination. I made him imagine that I was a woman, and had him practice approaching me. He clearly felt awkward, as women in tight skirts and heels glanced at us as they passed on the nearby sidewalk headed toward the bars.

In that lesson, I taught him how to look women directly in the eyes, stand upright, use his voice to command attention, and use touch to put people at ease. When I thought he was ready, we walked over to Pianos, a small bar and hot spot for attractive young professional women. Based upon our initial conversation, that was the type of women that Jason wanted to meet.

As we entered the bar, fear strangled Jason’s body. His breathing shortened, his shoulders knotted, and his voice rose in pitch. I understood what Jason was feeling; he was terrified of female rejection. It was once terrifying to me, but by putting myself into situations in which I was forced to approach and meet women, I overcame it, and so would he. “They’re just girls,” I assured him. “Breathe deep, relax, and talk to them. They’re here to meet someone too. See those two tall leggy blonds? I want you to approach them.”

Terrified, Jason froze up and refused to approach the girls. My experiment was failing. I searched the room for solutions. I recalled a memory of being six, and afraid of the dark. I would lay in bed, scared of every sound and shadow, unable to sleep. Sometimes I’d get so frightened that I would break a toy scrambling toward the light switch, only to discover that nothing was there. I considered the memory, “How could I show Jason that there was nothing to be afraid of?”

“Here’s what we’re going to do,” I told him. “I’ll talk to the first few groups or girls so that you can see how it’s done. You’ll see it’s not so bad. Then I’ll have you go.”

I started with a gorgeous blue-eyed brunette, standing with her friend near the bar. After a few minutes and a phone number, I moved on to a pair of blonds. I brought Jason into both of the conversations so that he could see how to use the tools I was giving him.

“You have to introduce new topics into the conversation.” I told him. “You’re a stranger so she’s probably nervous. If she’s attracted to you she’s even more nervous. That’s why it’s important that you lead the conversation. Use open-ended questions to get her talking. Make it easier for her.”

I demonstrated by approaching a group of women, “Hi, what do you think of traveling alone?” I then moved into the reason for the question. When the conversation started to slow, I’d ask another one. Occasionally, she’d ask me a question. The conversation developed a natural flow.

As the night progressed, Jason’s shoulders relaxed, his breathing slowed, and a smile tickled his lips.

I placed my hand on his shoulder, “I told you, they want to talk to you.”

He was excited as possibility cracked apart his mind. His limiting beliefs about the world, other people, and himself were shattering.

“Okay. I’m ready.” He looked straight into my eyes. “I want you to do the whole thing.”

“I’m confused, what do you mean?” I asked.

“I want you to take someone home.”

“You mean have to have sex?”

“Yeah.” He was serious.

I stared at him in disbelief. When I put the ad on Craigslist, I figured I might pick up a client who was feeling lonely, and who had been on the site looking for a prostitute, someone who was paid to have sex. I was now wondering if I had just become one.

But his request was logical. I had showed him how to approach women, and how to introduce new topics to make his conversations last longer. As he imitated me, the strategies that I taught him had worked. Now he wanted to see the entire process so that he could try to replicate it for himself.

This created a moral dilemma. I wasn’t against going to a bar, meeting a woman that I liked, and ending up in a situation in which I was physically intimate with her, but if I did, it was my choice. Something felt wrong about having a stranger pay me to approach women and take them home. Some men might think this sounds awesome, but when it happened, it was weird.

I cut him off, “We’re over on time.”

As we walked toward the subway, I thought about the $150. I hadn’t collected it yet, and I needed it. I was attending a college that I really couldn’t afford. My classes were so intense that I couldn’t get a normal job. This guy was my only source of income, and I didn’t know when I would get another. As uncomfortable as his request was, I needed to sign him up for another session so that I could afford to eat and pay my bills. I looked around for a subway sign, back at Jason, and around again for direction. My morality and needs attacked each other. Only one could win.

I saw a group of women on a street corner. I interrupted them, and hoped for help. “Hey guys, do you know how to get to the subway?”

“It’s three blocks that way,” the woman pointed with her finger.

“Thank you.” She was beautiful, and so were her friends. “I love your necklace,” I said, picking it up off her chest to observe it. I grazed the skin around her collarbone with the back of my hand. I noticed that she didn’t jump.

I introduced myself with a handshake, lightly shaking with my right hand while I softly touched her shoulder with my left. I watched for tension, a sign that my presence made her uncomfortable. It never came. As I released the handshake, I slid the hand on her shoulder down her arm so that I was holding her hand.

As we talked, she smiled and I squeezed her hand. She returned the pulse back to mine. It was obvious that she felt comfortable with me. Jason stood on my left, and watched everything.

“How do you girls all know each other?” I asked. I needed to know their relationships. Whether they were friends, family, coworkers or acquaintances. Who had boyfriends, and who was married. If a girl had a boyfriend, was his sister there, and what was she like. I needed to know why were they out, and who was leading the group. These things were important because they would influence each woman’s behavior as I interacted with them.

“It’s our friend’s birthday,” she explained.

“Introduce her to me.” She led me by the hand through the group.

The birthday girl (BG) was a cute dirty haired blond in her early to mid twenties. She was well dressed, sexy, and exactly the type of girl Jason wanted to meet. Jason followed by my side.

My new friend interrupted a conversation the BG was having with a friend, “There is someone that I want you to meet.” She finally released my hand.

The BG looked up at me and smiled. She introduced herself and placed her hand on my arm. Her name was Kate and her touch disclosed that she was attracted to me.

“Happy Birthday,” I leaned in to kiss her cheek. I noticed her reaction as my lips touched her skin. I scanned for signs that she was uncomfortable. Changes in breathing, tension in her arms and neck and shoulders, her reaction as I entered her personal space. There were none. After the kiss I pulled back. We looked directly into each other eyes, and that’s when I felt it.

Placing my right hand on her cheek I leaned in. I had known her maybe ten seconds. We began kissing wildly on the sidewalk. Jason, her friends, and the entire world slowed and then disappeared for the next minute.

I pulled away first, while she panted to catch her breath. A smile filled her face as she looked me over, “I would do crazy things to you.” It was obvious what she meant.

I turned toward Jason, who still was standing at my side. For the second time that night, he couldn’t speak, but this time for a different reason. I looked directly into his eyes, “That could be your life.”

We turned from the girls and started toward the subway. On the way, Jason paid me and we scheduled his next lesson in love.

Chris Luna

Founder, CEO, and Head Dating & Life Coach @ Craft of Charisma dating and relationship coaching.


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