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On Life, Love and the Pursuit of Happiness

The Guys' Guy's Guide to Online Dating (Part 3)

Robert Manni - Monday, May 23, 2016


I was still determined to master the art of online dating by using my skills as a long-term marketer and advertiser. I reminded myself that my profile was not for me. I was not the customer. My profile was for the person I wanted to date.

So I reviewed my profile and once again asked myself what I wanted, what made me different, and what I had to offer a woman. It’s easy to be self-critical, but we’re all special in some ways. I identified the qualities that I thought separated me from the herd and asked a few women I knew if they agreed. I asked them what they looked for in a man. Most of them wanted to date a guy with a job, a dream, confidence, and a sense of humor, kindness, and relatively good looks.  I used this feedback in my profile and made sure there were no typos or grammatical errors. I also changed my specs for the type of women I was interested in meeting. I realized I wanted to date women who knew what they wanted, shared my values, and were emotionally available. Finally, I expanded my geographic search parameters beyond the world of Manhattan and the ‘lists’. You may have read about women’s lengthy lists of must-have qualities men need to have to be even considered datable. My advice? Shake it off. Be yourself because nothing beats authenticity. Ultimately, everyone wants to be with someone who’s interested in the real person, not the “best front” we sometimes present during our initial weeks of a courtship.

Then I went back online. I decided to keep my contact rules in place before meeting anyone in person. If things did not feel right when we met, I wouldn’t waste our time. I’d share a drink and move on. However, even if there was no spark or the possibility of a romantic connection, it was important to treat the women I met respectfully. In today’s digital dating scene, it’s easy to disappear like a ghost or simply delete someone with a keystroke, but we’re dealing with people who are just like us. People who have feelings and who are also searching for a connection. So if there was no real chemistry with my date, I did my best to keep the conversation going until she finished her cocktail. It was the least I could do. As a result, some of the women that I met became friends. In fact, a few of them even set me up on dates with their cute friends. It pays to be nice.

With my newly updated profile, I was getting better responses from women than when I first signed up. When I saw someone I was attracted to, I read her profile a few times to get a sense of whom she really was. I made sure her bio wasn’t laced with, “Me, me, me…” or  “I don’t like…” I’d send a brief note— never a wink or a poke. I’d also mention something she had included in her profile—maybe that Korean dish she made or her recent trip to a yoga retreat. I might also add something about me that wasn’t in my profile. If she replied, I’d respond with another short note and my phone number, full name and personal email address. This way she could Google me to make sure I wasn’t an axe-murderer. If everything checked out, I’d suggest that all important phone call. Most women sent back their phone number so I could initiate the first call.

If the call went well, I’d suggest meeting for a glass of wine or coffee depending on her preference. A word of caution—no matter how great things might feel during the email and phone call, don’t invite someone to dinner without first meeting them in person. As mentioned, the vibe could change dramatically when meeting for the first time, and first dates can take bad turns. If you have dinner with someone you’ve never met and there’s no chemistry, it can make for a long, uncomfortable, and often awkward evening.

As I continued to date, I also continued to fine-tune my set of rules. I found that when meeting someone new, it was best to make it a short night. If things were clicking, I’d suggest a second glass of wine. If things were really going well, I’d offer to take her someplace else for a quick bite. Then I’d call it a night and hail her a cab. I found that a show of restraint added a sprinkle of mystery and stoked the anticipation of a second date. Soon I was dating more and more interesting women—clothing designers, entrepreneurs, fitness models, photojournalists, and teachers, along with selected professionals and corporate types. Most importantly, I was connecting with almost every woman. After a few months of non-stop dating, I got into a relationship with an attractive woman, took a break from the site, and dated for a year. After the relationship ran its course, I logged back on the site, reviewed my profile yet again, made a few more tweaks and in no time began dating like crazy for another year. My online dating system was working like a well-oiled machine.  Having a clear set of rules helped, but I soon found out that, as in life, when it comes to online dating there are no unbreakable rules.

Like other indulgences, online dating has a shelf life. I reached a point where I was content. My system was doing a lion’s share of the work. Dating had become easy. And as soulless as it sounds to me now, at the time, I thought I’d be happy dating for the rest of my life. Everything changed though late one night when I logged onto the site. A new woman had winked at me. She was pretty, even if her photo was a random late night selfie without makeup. I was intrigued by her photo and by the carefree flow of her profile. So I began the usual process. I emailed her and she replied the following day. We exchanged another email. The vibe felt right so I sent her my number and suggested a phone call. However, this woman did not think that a phone call was necessary. She suggested that we meet in person. I wrote back, trying my best to arrange a phone call, but she again declined. What about my rules?  I needed to make a decision.

I was torn. My rules worked. Why should I change? I read her profile again and stared at her cute photo before my intuition kicked in. This feels right, so, what the hell? It’s just a rule that I made up. We skipped the call and met on a balmy July evening. Things went well. Real well. And I wanted to see her again. I followed up by text after our date and we got together again the following week. Out of curiosity I looked up her profile again, but it was gone. When we got together for dinner I asked why her profile was hidden. She told me that she’d only signed up on the site for a three-day trial. Since she had a good time she wanted to give us a chance. She saw no reason to stay active on the site. I wisely deleted my account shortly after and we were engaged one year later. We’ve been married for six years. I know now that online dating is an art, not a science. It’s okay to go with your gut and break your rules now and then.

The bottom line is that if you pay attention to what you are putting out and who you are, online dating can be fun and fruitful. You might stub your toe and get your heart broken a few times along the way, but you can win. Always show respect for yourself and the people you meet. And, don’t take anything too seriously. Remember; dating and meeting new people can be an adventure, not something that creates anxiety. If you take the time to build your personal brand (know yourself, what you want, and what you have to offer), communicate clearly both online and in person, and display the confidence from a well-lived life, you’ll be on your way to making the right connections.

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