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Confessions of a Serial Hook-Up Artist

Confessions of a Serial Hook-Up Artist

I was a master at creating false intimacy. Until I realized I was missing out on true love.

by

In my late-20s I figured out I was pretty good at dating. I spent significant time diligently learning all the "rules" and applying the gentlemanly behaviors I’d been raised with. I met hundreds of women through work, on the street, and online dating sites – all with the objective of getting them to want to go out with me.

The "rules" were: Use good eye contact; smile; pay sincere non-threatening compliments about things they choose in their appearance (shoes, a necklace, eyeglasses); ask appropriate questions and listen to the answers with interest; offhandedly suggest that we meet again; and most importantly, get a phone number.

I would take notes after the meetings to boost my powers of recall (it was a lot to keep straight) and appear even more sincere. Two days later (not one, and not three), I’d call with a plan for a date, indicating that I’d listened to everything they shared when we’d first met.

Before the first date I'd make sure the car was clean and that I was moderately fashionably dressed – especially the shoes (women seem obsessed with shoes). I’d pick her up 10 minutes late (to be sure she was ready), and head out.

I was a master hook-up artist and that made me feel good about myself.

On the first date, I would open the doors, pick up the check, listen more than speak, be careful with alcohol (one glass of wine, no more), and have a plan for the next meeting. This approach continued with little variation in strategy or results. The first date led to second, which led to third. Within a few weeks I invariably found myself in an intimate relationship with a person I didn't even know. I was a master hook-up artist. I was a master hook-up artist and that made me feel good about myself.

For a while.

I didn't create this narrative as some kind of how-to guide. I'm trying to explain how truly unromantic and devoid of honest human feeling the entire process was for myself and others. It was a time-consuming game that many young adults play – and then complain they missed the boat on marriage and children.

I almost did.

There is a better way for things to happen that changes the whole nature of dating from sport to relationship. You get to know a person as a person – their interests, their goals, their beliefs. You hear about their families, their careers and their childhood crushes. You carefully observe: Are they neat or messy? Do they get angry quickly, or have a way of soothing others? Do they live their beliefs, or simply pay lip-service?

Do you actually like this person? More importantly, do you respect them?

Then you decide to have a relationship. You connect and commit intellectually, emotionally and spiritually – before even thinking of physical intimacy. It takes time and effort and – when done properly – produces lifelong intimacy on all levels that makes every other human relationship pale in comparison. That's the way things are supposed to happen.

I blew right past the “getting to know you” stage into false intimacy.

But that's not how it was happening in my world. I blew right past the “getting to know you” stage into false intimacy. And once things get to that point, they never seem to circle back to the “getting to know you.” You're stuck with what you've got and convinced by all the dramatic, exciting things going on that it will work out.

Invariably one of us would sober up and decide to move on. It might be a few months, a few weeks, or even a few days. (One lasted two years and I almost got married!) Occasionally I'd recycle things with an old flame after a time if I wasn't finding enough new excitement on my own. But each time, as soon as one ended I was off to the next.

True Love

It might appear that I was manipulating the women I dated, but I assure you I was not. There is an entire subculture based on this type of false intimacy. Just as I was engaging in a lifestyle of serial monogamy, so were the women I dated. That's what we did during that time and place in life. These women had careers and goals, and most were probably more self-aware than I was. That's why they played along. They, as much as I, wanted this faint shadow of things that go along with marriage – without all the actual work and commitment involved. Since I observed the "rules" and followed the guidelines of gentlemanly behavior, these women considered me a “good guy,” and so it was all okay.

I did this for seven years.

I started my own business and had some money in the bank. I had a regular Saturday morning foursome on the golf course. I lived in the most beautiful city in the U.S. I was dating the current “love of my life”.

Then I started attending synagogue, exploring Jewish spirituality, and I began to think about things a little differently. I realized something was wrong. I should have been happy, but I realized how lonely I really was. How little value I was attaching to myself and what I had to truly offer others. I realized that for all the dating and romance, I hadn't been in love for many years. Later I would realize that I had never really been in love, ever.

I realized that for all the dating and romance, I had never been in love.

I stopped chasing after the then-“love of my life” and she didn't really mind. She didn't get the Jewish Friday night thing, anyway. I dropped my Saturday foursome and gravitated toward a more observant lifestyle. I started to make friends that shared my values and began to figure out who I was and what I wanted.

I stopped dating for a while to give myself the needed space to introspect and explore. After about a year I asked out one of the women I had become friendly with at the synagogue. After dating for a few months, we decided that we weren't suited for marriage and we moved on. We remained friends – probably because we were friends before we dated and we stopped dating before any feelings got hurt.

Then I met my wife. She walked into the room took my breath away. We went out for a cup of coffee and talked for hours. She, like me, was clear on the fact that she was dating for marriage. That's definitely against the "rules."

The next day I couldn't help myself, I called and left her a voice mail saying how I had a great time and wanted to see her again. I broke the "rules" again.

Two Sundays later we went to a kosher winery, had a picnic, and talked from morning to night about the things that we wanted. Who we were. What we believed. How we wanted to live. We talked about faith and careers and money and children. That is absolutely against the "rules."

We met several times a week. I met her parents. She met mine. We met each other's friends. We attended synagogue together. After two months, I proposed. She said yes before thinking and then said yes again after catching her breath.

Burning Bush

We married six months later and in the four years since we've been through financial crises, family issues, lost pregnancies, career changes, and been blessed with a beautiful daughter so late in life. We're business partners and friends. I am absolutely not lonely anymore. The excitement of finding a new woman to date is nothing compared to the adventure of discovering new things about myself and my wife every day. And it's nothing compared to raising my daughter.

But here's the thing.

For seven years my wife’s office was three blocks away from me before I met her.

For seven years my wife’s office was three blocks away from me before I met her. We discovered that we parked in the same parking lot. We lived a few blocks away from each other for two years, and vaguely remember bumping into each other at a neighborhood convenience store. We both have a sweet tooth and ended up there on late-night candy runs at the same time on several occasions. There were a number of other near-misses.

We're now in our mid-40s. While we're thankful that the Almighty finally stomped His foot hard enough for us to get the message, we really would have liked to have met each other earlier. We love our infant daughter so much that it kills us to think that had we met earlier, we might have been blessed with five of her by now.

The first time I studied the Torah portion that talks about Moses and the Burning Bush, the rabbi asked the study group how long we thought the bush had been burning before Moses noticed it and turned toward it. I think about that a lot these days. With all those near-missed meetings with my wife, that bush must have been burning for years before I saw it. I wasted seven years, blinded by "false intimacy" and the year I spent recovering from it. What if I would have seen it earlier?

It's hard to be out there in the world and be single. It's hard to see people that seem happy serial monogamists and not want to try out the lifestyle while waiting for your true mate to show up. I thank God every day that I got out of it in time to meet my wife and daughter. I shudder to think what might have been, and for so many others out there, what still could be.

Published: April 1, 2013


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Visitor Comments: 22

(19) Anonymous, December 23, 2013 4:04 AM

You should just know, that while I understand very well why you both wish you had met significantly earlier, this whole journey was G-d's plan for you. B"H you made it!!

(18) E. Deutsch, May 22, 2013 7:18 PM

Thank you for writing!

I thought this was a superb piece. The lesson is great and relevant to me as it shows that we can waste precious time in frivolous pursuits and that even though we may and hopefully will come to the truth later on in life - so much heartache can be avoided if we put in the work and do the thinking NOW. Thank you for sharing your story. Always higher.

(17) Bobby5000, May 20, 2013 9:30 PM

the right time

Good article. One wonders whether he would have had the same satisfaction in his marriage had he married earlier. Having experienced dating multiple people, he can now seek satisfaction and fulfillment in finding the right person. Outside the Orthodox community, many parents would rather their children date and find the right person in their late 20's or early 30's.

The lesson for women is that they really didn't know their dates before engaging in intimacy. They just knew he dressed reasonably well and followed societal norms. Do you help the poor, engage in Tzedakah, treat people well are more important that wearing the right clothes.

The lessons are the same for boys and men and they will find some attractive women who are not really good people.

(16) Jane, April 6, 2013 11:07 PM

It's a sad commentary on women that the approach worked so well

(15) Anonymous, April 5, 2013 12:03 PM

Amazing Heartfelt Story

Wow!! This is a truly educational piece. I must show it to my sons. And it is significant to note, that you found right on time, that beautiful light from Hashem, to guide you towards real love. May the Almighty bless you, your wife and daughtet. Thank you for the wonderful article.

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