A Game of Taboo, Anyone?

25 Nov

In much of the Midwest, particularly Wisconsin, online dating is still very much a taboo subject. When you mention that you have a dating profile, looks of shame and judgment, coupled with hand-over-the-mouth gasps, typically follow. It’s normal. Expect it.

Around here, people are accustomed to meeting people in traditional ways: through other people; at work; or, especially in Wisconsin, at the local watering hole with Old Milwaukee in hand and tunes of old jukebox music in the air. But go to most major U.S. cities, and you’ll find that online dating is embraced. There, young professionals seek to establish themselves in careers. There, 30 is the new 20. There, people are waiting longer to get married and start families. And only when their careers are successful are they ready to begin seeking partners. Meeting someone would seem easy in a large metropolitan area where people are everywhere, but snagging one – the one – is a constant struggle for hurried, agenda-laden people who have forgotten how to connect. So online dating is their answer.

Online dating enables a lonely heart to save time, to be an efficient dater. Why go on awkward first dates when you can search thousands of profiles to see what you’re getting yourself into? Weigh their credentials with your criteria. Evaluate photos for physical attractiveness. Get to know their stories before they can tell them. Judge them. Discover their ambitions and career goals. Then, separate the wheat from the chaff, ultimately selecting the lucky one.

Despite my conservative neighborhood’s stereotype surrounding online dating, I gave it a shot. Maybe it was the hopeless romantic in me, bravely buying into the “you never know” battle cry. I met all types of women from different backgrounds. Younger. Older. Blonde. Brunette. Athletic. Girly. Funny. Smart. Blue eyes. Brown eyes. Full figured. Slim and trim.

Here is my account of the various women I met.

Carrie was “my first.”

Sweet. Athletic. Great with kids. Tall. Blonde. Intelligent. Ran a daycare program at a local health club. She sent text messages with unceasing overabundance (but I was new to the experience, so I didn’t mind too much). On the eve of our date, I actually picked up Carrie at her place, something that surprised me because, in the book of online dating (which doesn’t exist but should), the general rule of thumb is to meet at the restaurant or risk becoming tomorrow morning’s headline (serial killers really give online dating a bad name).

Dinner went well, minus running out of things to say near the third hour (lesson learned: yes, less is more). And then the awkward, nervous “May I walk you to your door?” I tend not to kiss on the first date, yet I could sense the fear in her eyes, “What is he planning to do?” Gulp. But with a hug and a “goodnight,” I vanished into the midnight air. After that night, however, something changed. Her communication became less frequent, and she became distant. Sensing the change in her demeanor and knowing I had nothing to lose, I gave it one final attempt. So flowers were delivered to her work, affixed with a note: Will you have dinner with me again? Soon thereafter, I received a text message saying that she didn’t have the same feelings for me. Carrie and I never saw one another again.

Then there was Megan.

In school for fashion merchandising. A bit younger. Smart. Talented. Beautiful in her online photos, she showed up orange. Yes, orange. Apparently someone decided to go spray tanning before the first date. And spray tanning in Wisconsin in January makes you stick out like a sore thumb. The peach dress she wore didn’t do the orange hue of her skin any favors either.

Eventually, I got past the orange but couldn’t get past her references to things that proved our generational gap. And her never-ending use of the cell phone. My God. Constantly checking it. Over and over again. I should’ve known right then and there. Eventually, she relayed to me that some friends had asked her out clubbing, to which I responded, “Oh, you should go” (no one had clued me in that making post-date plans with other people was common, but what did a guy having been out of the game for too long know?). She seemed caught, trapped, yet she agreed to another drink. Saying goodbye was an awkward hug and never a look back. Later that week after thoughtful consideration, I decided to give her a second chance. What the hell? No one likes first dates (they’re awful), so maybe she was just as nervous as I was. She never responded to my follow-up message.

Brooke lived an hour away from me.

We hit it off. Not my type physically but humorous and unbelievably bright. A killer personality. I drove the hour to meet her for dinner (I’m a big fan of keeping it casual on first dates with pizza and beer). Two hours later, we said goodbye (she, too, had another post-date party to attend). Normally, I’d think that the post-date plans are either as an excuse to leave early or a sign of low expectations, but Brooke invited me along. I didn’t feel comfortable meeting her friends for the first time when I had just met her for the first time. We said goodbye. We may have gone out again, but our messages got crossed. As luck would have it, I never got hers, and she never received mine. In the end, each of us thought the other wasn’t interested, and, by the time we figured out what had happened, we had moved on. It was written in the stars.

Becky was someone made for me.

A bit shorter. Incredibly attractive. Funny. Very driven to succeed. Goal oriented. She had a solid career, and to this day I know she’s going places (not a doubt in my mind). Like me, she drove a MINI. And she, too, had just moved to the area and recently split from a long-term relationship. But our first date was missing something. I can’t describe it. A spark. A connection. I don’t typically read too much into first dates because, again, they’re awkward; second dates are actually more telling because we tend to be more relaxed, revealing our true personalities.

I don’t believe in love at first sight. I also think people put too much stock in instant chemistry. At the same time, chemistry shouldn’t require a complex formula to feel something. I’m at an age when I don’t want to waste my time with something that isn’t certain in my head and heart. I’ve been through enough relationships that I know what I want. While life has few guarantees, I want to make sure the next relationship is really right for me. I’m done experimenting with relationships that take years, only amounting to lessons learned. All in all, Becky left for a business trip the next week, and the timing killed any momentum we had.

Amanda was similar to Becky.

We spent an entire afternoon together. She made me laugh. Down to earth. Not the girly type, as even she confessed, “I’m lucky if I wear Chapstick, let alone lipstick.” I appreciated that, as I’m not a materialist guy; at the same, I want a woman who gets excited about and takes pride in dressing up for a night out. Like Becky, she had just ended a serious relationship and was struggling to meet people. Like me, Amanda was divorced, harboring many of the same emotions and sentiments which eventually made the way into our conversation. She also had a great career, having just relocated to the area (like me) to get a new start. An afternoon meeting at Starbucks eventually led to drinks on a patio overlooking the water. But when I returned home that night, I couldn’t help but think that we had a great time, the type of time you’d have with a roommate. While the day was fun, I again felt uncertainty about her being right for me.


The most confident women I’ve ever met. She actually initiated our online “relationship,” saying that I was adorable. While she was a bit older and at a different stage in life, I agreed to meet her because I never want to close doors of possibility. After various text messages and emails, we shared about four dates. She made me feel like the center of the universe. I liked her. On one of those dates, I visited her house. There, children’s toys filled the floor and family photos lined the walls. As hard as I tried, I couldn’t get past the fact that she had children. I wanted to. But I couldn’t.

And then I became the victim of my own pet peeve: I stopped answering her messages. I couldn’t bring myself to tell her that her beautiful children were the reason I couldn’t follow through. In a matter of a week, I went from potential date to being a potential “fatherly” figure thrown into the lives of two kids. Was I putting the cart ahead of the horse? Perhaps. But, looking ahead, the thought scared me; I wasn’t ready for it so soon. I do want children — my children. And the overriding sentiment was that it wouldn’t be fair to her kids. With that, I completely disappeared from her life. A blur. A blink of an eye.

The others.

There were countless others who never materialized into face-to-face dates. Like Courtney and Robyn. I wonder what happened to them or if they found love. I actually talked on the phone for hours with Courtney; Robyn never returned my phone calls. As online dating would have it, I received emails from countless other fish in the sea; but like a slight tug on the fishing line, enough to get your attention and falsely alarm you of a great catch, they swam away with the current.

Lessons learned.

Along the way, I learned much about dating in a social-media world. I also discovered a lot about myself, who I am, and for what I’m looking. I realized that forcing something like a relationship only fills you with regrets. And avoid regret by never settling. I discovered that everyone’s story is precious and different; that doesn’t make you a bad person, but it may make you unfit for me. I now know to never count something out unless you’ve tried it. I don’t trust a relationship that looks good on paper or on screen is guaranteed to be a match made in heaven. Therefore, I believe in the power of face-to-face connections and the value of personal communication. I learned to never give up hoping or trying. More importantly, I learned to never stop being me.

She’s looking for me somewhere, and someday our paths will cross. Until then, I’m independently happy, trying to enjoy the journey that is life. I’m still single, clinging to the idea that I’ll find it when I least expect it. Around any given corner. On any given day.

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Posted by on November 25, 2012 in Love


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