Whirlygig: 88: Out on the Town

Tales of dating misery run rampant along Loveland Bike Trail

Running in Place
Long gone are the days of sleeping until noon, lifeguarding and hanging out at the city park with a gang of friends that come with being a teenager in the midst of summer. But does that mean that we still can't enjoy a little bit of innocent dating?

When car dating was in and of itself a new privilege, drive-ins were forbidden fruit for dates — mostly because it wasn't all that innocent halfway through the movie. Now it's almost impossible to find a drive-in theater at all even if there was a guy I wanted to break the rules with.

In present day, I'm beginning to think the problem isn't will Mom and Dad allow it but will any of us be able to coordinate our schedules to actually come up with a mutually compatible time? Then, of course, there's the more important issue of whether both parties will be interested in future dating and activities that eventually will involve heavy petting with or without the drive-in.

As my buddy Mike and I were struggling to survive the heat and humidity of running midday Saturday on the Loveland Bike Trail, I asked him if he'd met anyone he wanted to make babies with lately. He grunted and shook his head.

"Anyone you want to practice with?" I inquired.

He grabbed me and pretended to pull me off the trail. For the moment that made me forget the heat and the stitch in my side. It was funny but not an option.

We laughed at our mutual dating misery and entertained each other with our frustrations for the next mile or so. Mike, it seems, is having a bit of difficulty finding a girl who's as interested in him as his net worth.

"Aren't you supposed to have fun getting to know someone?" Mike queried.

Yeah, I think so. But it's been a while since someone made me want to throw caution to the wind, and so maybe I'm wasn't qualified to answer.

He continued with a tale of a girl he took out two times who he knows through his interest in running. On the second date she asked him where it all was headed. He admitted to me he'd hoped that after a nice dinner maybe there would be dessert sometime in the near future but he wasn't pressing it as he had time and plenty of patience. It seemed to me that he liked this girl well enough and that they shared common interests, but maybe it was a tad premature to be picking china patterns.

The girl cooled it, and they went on a couple more dates before she again gave it the "let's get serious" talk. Mike admitted that he bailed. The intensity was off-putting. He decided there was enough pressure at work to choke a horse that having it over the fourth date was overload. I was in agreement but offered that her biological clock must be ticking like a time bomb.

It seemed fitting to offer a lament of my own from the recent past. I told him about my conversation with Sonya, a close family friend who's living in Chicago now. She's 25 or 26 and selling television advertising. Sonya lives in Lincoln Park and is being kind enough to offer her pullout sofa to us as we'll be in town next week for a tennis tournament in nearby Evanston.

When I mentioned wanting to go over to Bucktown for dinner in an outdoor café, it came up in conversation that she's currently dating a guy who lives in a house there but hasn't seen it yet. I assured her that Bucktown is a cool artist area and that his place is sure to be worthy of a look. She offered that the guy lived there with his wife. When I asked how long he's been divorced, she said it had been a long time.

"How old is he?" I couldn't help but ask.

"Thirty-seven," Sonya replied adding that they had no children.

Mike got my point readily enough when I told him he's lucky he too can date twentysomething as well as thirtysomething women. He offered that I could pull a Demi and date well beneath my age. I assured him that while it's fun to read about Demi and Ashton in the magazines it's less entertaining in real life. Dating 50-year-olds is the alternative, of course, since the men my age are all dating my ex-babysitters.

Uninspired by that thought, Mike went back to another situation that has him perplexed. He told me about a girl his sister swore looks like Christie Brinkley. He agreed to take her out on a date. His fix-up was cute, though not exactly as cute as Christie. He did say, however, that he's called to ask her out again. He's not getting a lot of interest from her, though his sister has asked him to be patient as there's a family member who's ill and that could be the possible explanation. We agreed that the timing could be off in this case and he should keep trying.

I mentioned a girl from his past who I know vaguely. He admitted he feels lucky to have gotten out of that one alive. She wanted to look at his W-2 from last year and was overly interested in his property holdings, which he rents as a side income to his day job. It unnerved him more than a little. As he says, he works with people's assets and credit ratings all day and doesn't want to do it in his personal life. His other concern was that when the going gets tough and someone is only in it for the money there's going to be little love to get a couple over the rough spots.

The other thing about his ex is that she complained he worked too hard. Mike does put in a lot of hours, no question. He admitted he'd cut back for the sake of family. Of course, married to a girl like her, I offered that it's expensive to keep her type in clothes, cars and country clubs. He threw in how appalled he was at the cost of her weekly nail appointments and asked me how much I spend on my hair, which I assured him is less than she does.

We were left sweating after running four or so miles. It's true that misery loves company, and not only in the exercise department. I thanked him for the Gatorade he bought me at the corner United Diary Farmers, and he suggested I try the tattoo-type talking on the payphone. I passed and headed home to take the well-deserved shower. Alone.

You read Whirlygig every week, now we want to hear your stories. Send them to [email protected]

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