60 First Dates–Single Again in the Internet Age

By Steve Kaplan

The Internet vastly accelerates the dating process.

The Internet vastly accelerates the dating process.

“I’ve been unhappy in the marriage and I’m leaving.”

I heard my wife make this astounding proclamation — and then I blacked out from the shock. How could she be leaving? We were partners, lovers, best friends – soul mates! But on that sunny Aril afternoon of 2002, my world came crashing down around me. When I came to moments later, I told her there was no way that after 18 years of marriage she could suddenly be so unhappy that she was leaving. There had to be someone else. And I could see by her face that there was. And she then admitted to having an affair with her massage therapist with whom she was deeply in love.

Over the next several weeks as the grieving stage of denial gave way to anger and depression, the stomach-turning reality set in that I was going to have to reenter the dating scene. I had never exactly excelled in finding dates even when I was young and had a full head of hair. My quiet demeanor and limited height of 5’ 6″ (and that’s stretching it a bit) contributed to an awkwardness around the opposite sex. When trying to meet a woman at a party or in the supermarket, I inevitably had trouble coming up with anything even halfway interesting to say. The thought of suddenly being single again at 45 was worse than terrifying, it was petrifying. It was the last thing I had imagined and the last thing I wanted.

16 months later

I was on the Royal Caribbean cruise to Alaska with my two teens in mid August of 2003. During the second evening at sea the ship hosted a singles mixer at one of the bars. As I dressed for the event, I felt conflicting emotions of both fear and anticipation. Would I have the guts to actually introduce myself to someone? If I did, what would I say? Would she be able to hear me over the loud music that would undoubtedly be playing? And if I managed to find someone interesting who was interested back, what would the next step be?

As it turned out, I was spared any type of potential ordeal since I was the only single of either sex to show up. This was exactly the kind of nightmare I had imagined in the dark days following the departure of my ex-wife: the anxiety, the embarrassment and the disappointment of the singles scene. But I was not in the least discouraged. I simply left the bar, walked over to the ship’s business center, sat down at one of the .50 cents per minute Internet terminals, and logged onto my dating sites. First I checked to see if any new intriguing women had contacted me. Then I began writing emails about the cruise and even the singles mixer. I sent one of the emails to a family member and one to a friend. I also sent one to each of the four women I was seeing….

Online Dating

While dating multiple people simultaneously might seem distasteful, it is becoming increasingly accepted in the new world of online matchmaking as long as people are honest about what they are doing. Being hopelessly business minded, ‘parallel dating’ certainly seemed to me to be the most expedient manner in which to accomplish my goal of finding a new partner. Over a period of 14 months, I had 60 first dates with women from southern California to Vancouver. The majority of these meetings were one-time affairs, but several of them did lead into mini-relationships.

Without the magic of the Internet, finding scores of appealing women who would accept dates with me would have been improbable — even given a decade in which to accomplish it. Meeting compatible people offline is far too slow. First, you need a social setting conducive to encountering another available single. Next comes the prerequisite mutual physical spark — without it, you probably won’t have the opportunity to spend much time learning about someone else. But physical attraction can also distract from critically evaluating other important compatibility factors such as complimentary personalities, shared interests and similar relationship objectives. Several dates together may be required in order to fully gather and assess this information.

The Internet, on the other hand, vastly accelerates the dating process by turning it upside down. The first step is to join a dating site where you create an online profile of yourself under a clever pseudonym such as Goodcatch893. Other members can subsequently view your relationship objectives, interests, personality traits and appropriate background facts. Most sites encourage you to post one or more pictures along with an essay about yourself and about the type of person whom you would like to meet.

You can then use a simple search tool to screen for members of the opposite sex who have the interests and attributes you seek, enabling you to immediately cull a list of potential dates from thousands of members. Scanning the pictures and physical descriptions of the resulting candidates should at least provide an idea about how attractive you might find them to be in person. Reading their information details and essays helps indicate how much you are likely to have in common.

The next phase of online dating involves initiating correspondence via email. Although composing and reading emails can be time-consuming, it is still much faster than meeting for actual dates. And it is surprising just how much a person’s writing style reveals about themselves. Once you get proficient at learning the nuances, you really get a feel for the person’s personality, intellectual level and sense of humor.

When an online relationship proceeds to the next level, you are finally ready to meet in person. It is only a face-to-face encounter that reveals whether or not the elusive chemistry factor is there. But unlike the offline world, you already have established a nascent virtual relationship making an immediate physical connection less significant than it otherwise might be. And while mismatches are certainly not uncommon, experienced online participants tend to become increasingly proficient at screening out incompatible prospects prior to meeting them in person.

The simplicity and efficiency of finding dates online has led to an explosion in the growth of Internet dating; it has surpassed porn as the largest category of online content. Half of the single U.S. population is now estimated to have visited an Internet dating site. There are thousands of singles sites including specialized services catering to almost any group you can think of – from seniors to teens, from married couples to gays, from Christians to Muslims, from dog lovers to wine connoisseurs. It is hard to surf the Web without seeing an advertisement for online matchmaking. Internet dating has transitioned from a niche phenomenon bordering on the edge of respectability to the mainstream.

First Five First Dates

In hindsight, I began my Internet dating experience before I was ready. I was still getting over the shock of my marital breakup…and was in fact only 90% of my former self (…if you haven’t tried it, the heartbreak diet can work wonders. I dropped 17 pounds in the first two weeks following my wife’s departure).

I felt increasingly depressed after each of my four first dates. I either ended up not being attracted to the woman when we met in person, or she was not attracted to me. The most hurtful moment came when I met someone for dinner after having things really seem to “click” between us by email and by phone. She was slightly taller than me, and I could see the disappointment in her eyes the moment we met (the dating site I used at the time only requested a 2″ height range on member profiles so she probably assumed I was a couple of inches taller.) After that experience, I made sure to emphasize my stature prominently in my profile by proclaiming that I could offer kissing without neck strain.

I had a breakthrough on my fifth first date. I met an amazing woman: intelligent, pretty, athletic, worldly and charming. After a few weeks of seeing each other exclusively, the time was appropriate to become intimate. Unfortunately, I belatedly discovered that I still was not quite ready for this type of thing. I broke down crying when we went to bed together. Now, in case you have any doubt, I can assure you that this is NOT an effective dating technique!

But after a few more weeks passed, I decided to hit the keyboard again, and this time I was better emotionally and mentally prepared. I joined a more sophisticated Internet dating site and learned how to use its search criteria to more effectively screen out incompatible prospects. I spent more time getting to know someone through email and phone calls before arranging to meet her in person. Perhaps most importantly, I relaxed my expectations. Rather that focusing on a single-minded goal of finding a perfect mate, I decided I would instead become a seeker of knowledge. I would treat Internet dating as an adventure. I would see how much I could learn, but make sure to enjoy the whole experience!

I did end up gaining quite an education with some associated funny episodes. For instance, early in my online dating adventure I had been corresponding electronically with two ladies named Jan and Jeri. I had made first dates with both of them, but a subsequent email to Jeri inadvertently addressed her as ‘Jan’. “Who is Jan???” came back the terse reply. Since Jeri’s previous emails were long and full of deep musings, I knew that she was not at all pleased. But I was honest and told her that I was also corresponding with someone else. In anger she canceled our dinner, and I never did get the opportunity to go out on a date with her. This means that I clicked with someone, shared deep thoughts and feelings, cheated, got caught and ‘broke up’ without ever even meeting.

At another time, I was corresponding with a cute lady named Patty who told me she had an identical twin. “Really?” I exclaimed. “Is she single?” “Well no,” Patty replied. “She’s married. But why do you want to know that…I’m available?” “I realize that,” I responded. “But if we start dating and hit it off the first thing my single friends will ask me is if you have a twin. And it would be great to say yes!”

Caveat Emptor

Although Internet dating continues to grow ever more popular, it is not all roses. For one thing, people lie. They lie about their age, about their weight, about their height, about their income, about their smoking and drinking habits, about their marital status, and about their background. They put up pictures of themselves 5 years old and 25 pounds ago. Ethics aside, this kind of behavior is foolish. Every good salesperson knows that in order to build repeat business you should under-promise and over-deliver. The same holds true in online dating which, when it comes down to it, is a form of sales. This is particularly true for men since they vastly outnumber women on the Internet.

Some people believe that they tell the truth about themselves in their profiles, but their self-perceptions do not jive with the way the rest of the world sees them. They may, for example, think they are charming and witty while everyone else considers them self-centered and boring. This discrepancy in realities can lead to bitterness when their dates learn that they have been deceived, albeit inadvertently.

The Internet’s anonymity often leads to irresponsible dating behavior. In the offline world, people frequently meet their eventual dates through a social connection…whether work, friends, church, the gym, etc. They consequently tend to think twice before treating their partners rudely because of the likelihood of continued encounters with them or with others in their social group. On the Internet, people meet in isolation. The lack of social accountability makes it easy to deceive, be unresponsive or simply break off a new relationship without much cause.

Perhaps the most dangerous aspect of all, though, about online dating is the very success it enables. Experienced users frequently grow restless with their relationships because of the siren call of the Internet. There is always that nagging feeling that going back online and spending more time searching might result in finding someone new who is even more desirable.

60th First Date

Despite its drawbacks, Internet dating is a very positive societal development. Success stories abound of marriages resulting from online dating. And while the Internet might encourage increased relationship churn, it also enables people to find others more compatible with themselves. The optimist in me believes that this in turn will ultimately lead to better and longer-lasting relationships.

The dating process itself proved to be very healing for me and helped repair the self-esteem that was crushed as a result of my marital dissolution. And the experience, rather than being the torture I dreaded, actually ended up being a lot of fun. I met some really nice, high-quality women…several of whom I remain friends with even though we no longer date. I also learned a lot about women and even more about myself. And my 60th first date was my last as I am now contentedly in an exclusive relationship.

Steve Kaplan is in sales management for a national computer integration company that purchased the businesses he formerly co-founded and ran. Steve is currently writing a book about how to market yourself online and is the co-author of two technical books (Osborne/McGraw-Hill). He can be reached at roidude@hotmail.com.

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