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On Life, Love and the Pursuit of Happiness

The Guys' Guy's Guide to Online Dating (Part 2)

Robert Manni - Monday, May 16, 2016


It’s said that necessity is the mother of invention. I couldn’t agree more.

Take my experience for instance in online dating. After being with a woman for five years, one day she said that the relationship was over. I’d always thought that when a woman had issues with the relationship, her guy would be the first person to know. I assumed that the woman would want to have, you know—the talk. But in this case, she packed up her bags and was gone. I found out a few weeks later that she had already moved in with another guy. I was blindsided and devastated. Man, I was pissed off. But once I had time to really think about our relationship, my emotions shifted from pain to relief. I realized our relationship really hadn’t been working and I owned up to my share of why it went wrong. I asked myself if I wanted to be with a woman who was unhappy and didn’t want to be with me. And the answer was, of course, I didn’t. I was glad it was over.

It took some time, but I licked my wounds and self-assessed. I definitely did not want to make the same mistakes again. When I felt I was ready to meet new women, I realized, most of my friends were married and had kids, so they were not going out to meet women with me. So, initially I returned to my old habits of trolling the bars, gyms, classes, and bookstores alone. Hunting as a lone wolf soon proved to be a tough world for a guy over forty, especially after years of being in a live-in relationship. So much had changed that soon, there was no fun going out on my own. After a few lonely Friday and Saturday nights, I had to do something new. I decided to give online dating a try.

I signed up at the most popular online dating site. Like most guys, I slapped together my profile and anxiously dove into the fray. At first, I perused only the women with pretty pictures and pursued dates solely based on women’s photos. As a result, I met a lot of attractive women. I’d sit across from them thinking, they’re nice looking, but where’s the ‘spark’? Something was definitely wrong. I was not using the head perched on my shoulders to make my decisions. I was wasting a lot of time and money meeting the wrong women. I needed a reboot. The best thing I did was to take a break and hide my profile. I reviewed my personal brand (who I was, what I was looking for, and what I had to offer) and reworked my profile making sure it had the right messaging and photos to attract the type of partner I was looking for. This was the first important step in developing an online routine that finally worked for me.

After reposting my profile with a new headline, photo, and bio I went back to the work of dating. I set a few directional rules for myself. I decided not to invest too much time with online connections I met online before deciding whether or not to move forward. I’d exchange a few emails, maybe starting with a compliment or question about something in her profile. Then, if I liked her response I’d decide to talk on the phone. The call was always helpful. Nowadays, after a text or a tweet, people meet up without having a call. I wouldn’t take that chance too readily. The energy exchanged when emailing or texting is quite different than what we experience on a call. I’ve had experiences where the emails would flow with wit and élan, then come to an awkward silence when I got them on the phone. And even if that first call lasted an hour it did not guarantee success. Very often the energy dramatically changes, again, when we meet someone in person for the first time. I’ve found that we can’t control chemistry, and it’s impossible to predict. I paid attention to how the energy felt at every touch point—from first contact online to email, then to a phone call before asking a woman for a date. All this saved a lot of time and disappointment.

In time, I learned that, like my initial foray into online dating, other people also charged in without figuring out what they wanted from the experience. There were a lot of lonely people out there. And many of them were over forty and desperate for love and attention. They’d sign up on a dating website in haste and plunge into the unchartered online dating waters like new members of the Polar Bear Club on January 1st. After a few failed dates and often the icy chill of rejection, many singles withdrew from these websites as quickly as they dove in.

Here’s an example of what happened while I was developing my online dating chops. I met a woman for a date at a bar in Manhattan’s Flatiron district. She was a senior-level television executive. She was attractive, successful, and immaculately dressed in a white designer suit. We’d exchanged two short emails and a quick phone call before agreeing to meet after work. Everything felt good and I was looking forward to our date. Over small talk and a glass of wine I sensed the tension in her voice and body. I asked her about her job, thinking that she’d had a tough day. She told me she worked in television ad sales and she was having a banner year. So I asked her how long she’d been dating online. She said I was her first date. She’d signed up for the service the day after her long-term boyfriend dumped her. Initially, I thought that was a favorable omen for rebound sex, but she was so out of sync that I didn’t want to get intimate with someone in her vulnerable state of mind. I asked her if she had considered taking some time for herself before jumping back into the dating scene. Her eyes welled up with tears. Then she said, “I don’t want to be alone.” Sadly, this attractive, high-powered television executive was an emotional shambles.

This was not the first time I met someone who was obviously not ready to date. I consoled her over a Chardonnay before grabbing the check and hailing her a cab. The following day, Ms. TV Executive sent me a lovely email, thanking me for being so understanding. But our short night was another reminder that I needed to do a better job when screening dates. I was still doing something wrong. Many of the women I had met were fun online and on the phone, but uptight and anxious in person. Between learning about their lists of must-haves or surviving first dates that felt like job interviews, this online dating thing was quickly lose its appeal. I realized that I kept going out with women who reminded me of my ex—corporate stars who were not enjoying the ride. It was time for another break from the site.

To be continued…

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