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Surviving Rejection (The Pickup Artist Experiment)

I told my friend Jay Freshwater this story over twenty years ago and just learned that he’s been sharing it with his sales teams ever since. It’s my sincere hope that you’ll find the embarrassment and misery of my constant rejection as helpful as Jay’s sales teams. Enjoy!


I was devastated after a bad breakup in college. My ex-girlfriend broke my little heart. With my confidence shattered, I walked around sulking for months. I couldn’t bear another rejection, so I simply stopped dating. Poor, poor pitiful me.

On a trip home, my father noticed my pathetic state and sat me down for a little talk. He was understanding and empathetic, but he also knew the importance of moving on. So, he gave me a little advice (note: Dad’s advice was often a little nutty).

Dad asked me, “How many people go to your school?” It was over thirty thousand students.

“How many of those kids are female?” At least half.

He said, “I know it hurts right now, but there are over fifteen thousand ladies walking around that campus and you’re going to let one get you down? Think about it, son… you’ll never be around so many cute, eligible girls your age for the rest of your life.” Ok, that had some merit.

“In fact, you could date a different girl everyday for the rest of your college career and not take the same girl out twice.” That was a weird way to put it, but he had me thinking.

Still despondent, I responded, “I know there are plenty of women out there… that’s not the point. My problem is I’m afraid to ask them out.”

“You have to get over this fear of rejection,” Dad replied. “The only way to do that is to get rejected. A lot.” I didn’t like where this was going.

“Dad, that’s exactly what I’m trying to avoid,” I said.

“Exactly,” he said. “Here’s what you should do: ask out a different girl every day.” He could tell I wasn’t buying it, so he followed that up with, “I dare you.” Dammit! Don’t you dare me, old man.

“Okay, I’ll do it.” Dammit, again. Did I just commit to this? “For how long?” I asked. “Do it for the rest of the school year.” We were still in the fall semester, so that was about a six-month commitment.

Here were the parameters of this little experiment:

  1. I couldn’t afford to go on a dinner date every night (not that I thought I would), so I defined a date as anytime an offer was accepted. That could be dinner, a movie, or a concert, but it could also be coffee, lunch, or ice cream. It had to be a one-on-one experience. Group gatherings didn’t count.

  2. No set-ups. I had to approach and ask her out on my own.

  3. No one in my social circle. In fact, I didn’t want my friends to know what I was up to, so I didn’t tell them. This challenge was both crazy and embarrassing. Only a few of my closest guy-friends knew at the time.

  4. I had to ask at least one lady out a day with no exceptions. But, I could ask more than one lady out if I wanted to.

  5. I wasn’t looking for my next girlfriend; I was only looking for a date. This greatly opened the field of potential date candidates.

There was no “swiping right” back then; I actually had to meet a stranger face-to-face and start a conversation. In order to meet new women, I took myself out of my daily routine. I walked different ways to class, ate at different cafeterias and restaurants, studied at different libraries and stopped at campus bookstores at different times of the day.

In the beginning, the experiment went as expected. I crashed and burned early and often. I was soundly, thoroughly and often embarrassingly publicly rejected with each fumbling attempt in the first week. I was laughed at, ignored and insulted. Salt in the wound. Apparently, no one wants to go on a date with an awkward, slightly depressed guy with no confidence. People can sense desperation and it’s a turn-off. But, I kept going and I kept getting rejected.

After the first few weeks I realized the rejection didn’t hurt as much. In fact, it actually became slightly entertaining. In a short amount of time, I had stockpiled a collection of funny rejection stories. I was slowly becoming desensitized to rejection. Then I had an epiphany: The point of this exercise wasn’t to get rejected; the point was to get over the fear of rejection. Getting a “no” without the hope of ever getting “yes” is torture. So, I decided to change my strategy.

I would still ask a girl out every day and I wanted to get to a “yes.” Now, rather than worrying about the outcome, I would just focus on two things: 1) get her to laugh and 2) learn one thing about her that I would remember if I ever saw her again. If I could do those two things, it was a win for me even if she rejected my initial date proposal.

It worked! My first yes came as a direct result of getting a pretty classmate named Laura to laugh at a silly comment I made in Spanish class. This broke the ice and I took her to breakfast after class.

This gave me the confidence I needed to move forward. At my very best, my success rate of getting a “yes” or a phone number was somewhere around 30%, which is pretty good for a cold call. As my confidence grew and my technique improved I began asking two to three women out per day. Once I got on a roll I’d ask out anyone regardless of body-type, empirical attractiveness, or personality type. The greater the challenge, the more I wanted the date. Needless to say, this led to some interesting dates and priceless stories.

As you would guess, after getting to know so many women, I eventually found someone special. We began dating exclusively and the experiment ended.

Here are a few things I learned from this process:

The answer is always “no” if you don’t ask: We were at a school function one day when a tall, thin brunette with a radiant smile walked into the room. She was striking. Every guy in the room stopped what they were doing and stared at her. The three guys in my little conversation group all expressed their desire to meet her, but none of them actually approached her. So, I waited until the dust settled, walked up to her and started a conversation. I got her to laugh, learned that she loved to play tennis and wound up taking her on a few dates.

She was way out of my league, but I enjoyed my time with her. My buddy Paul asked, “How in the world did you get her to go out with you?” I asked her.

Life is a numbers game: Whether you are looking for a job, a client, or a date… life is a numbers game. As I mentioned above, once I figured out a sales strategy that worked for me, my success rate was about 30%. So, if I wanted a date I knew that I would need to ask about three ladies, on average, in order to get one “yes.” A “no” doesn’t sting as bad when you know there is a “yes” right around the corner.

Know your barriers to success and have a plan to remove them: To me, “no” meant not right now. There were typically three main objections… she just wasn’t into to me, she didn’t have time, and/or she had a boyfriend. Sometimes I heard all three reasons in one rejection. This will be difficult for my mom to read, but some girls just were not that into me. And, that’s ok. In these situations, my strategy was to be persistent without being a stalker. I was amazed at how many women would wear down and agree to a date after only three or four tries. If she didn’t have time, I’d get her number or a rain check. I knew it was her way of gently turning me down, but that’s when I would employ my strategy of persistence. If she had a boyfriend… see “situations change” below.

Situations change: About half of the women I met said they had boyfriends. I would still try to make them laugh and learn something about them. Why? Because situations change. I dated a number of women who had boyfriends when we first met. I still tried to build some rapport and then made it a point to keep in touch. When her relationship ended (as they usually do in college), the door of opportunity opened for me.

You never know. Eventually I learned which sales techniques worked on various personality types. I also learned that I had a “type.” I had a much higher success rate with a certain personality-type than others. However, that finding neither guaranteed success, nor failure. I was unmercifully shot down by women in my type and surprisingly accepted by women who were way out of my league. The lesson here is there is no such thing as a sure thing.

Rejection sucks. While it did get easier to get over rejection, I still didn’t like it. I learned that success was the best medicine. Identifying the “numbers game” was a revelation for me because the pain of a “no” evaporated with the next “yes.”

Finally, I was no pickup artist. In fact, I’m a pretty average guy and would be classified as introverted. I certainly wasn’t a Vince Vaughn-like life-of-the-party-type and I’m still a little awkward in social situations. Yet, I met and dated a lot of wonderful women (and a few crazies). Rejection is a part of life, but unless you can develop your own strategies to get over it, you will miss out on that big sale, job, girl or guy. If I can do it, you can do it.

“Only those who dare to fail greatly can ever achieve greatly.” Robert F. Kennedy


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