Dating Turkeys

By Lovable Cynic,

It’s holiday season, and because we’re all about the love here at, we’re giving you a chance to tell us about your WORST date…your holiday turkey. I work here and so I’m not allowed to enter the contest, but that won’t stop me from blogging!

If you read my previous blog entry, you know that I am now happily married, but getting there was a trip. In order to maintain my sanity during my post-divorce dating days I kept a journal of my most memorable dates and life as an Internet dater. The best ones I would share with my friends and family. This is the story of my first date, five years ago:

Lately, I’ve been thinking a lot about dating. I suppose that the main reason for this is that I have found it entirely too difficult to do. Because statistically, I am now knocking on AARP’s door (isn’t everyone?), some women believe that I no longer fall into the category of prime relationship material. Ah, but age is one of those deceptive quantitative measures. Witness the grandfatherly, OK, let’s be honest and call it feeble, visage of a Hugh Hefner. Hef has had more covert operations than the C.I.A., yet he still attracts women. Why? I don’t know and I don’t care to answer it here, although it might have something to do with the raw sexuality of facial crevasses.

It all starts with Jane (yes, her name has been changed, although her innocence is in question). I was living in an incredibly cool 6th floor bachelor loft. It had 1200 square feet of crazy, hipster, artsy-looking space with a commanding view of downtown Portland, Oregon and the West Hills. I couldn’t have picked a better place to live. Portland is a great city, and it has developed suburban sprawl that has extended across the mighty Columbia River into the state of Washington. True Portlanders would never consider living in Vancouver, WA unless they wanted to avoid state income taxes or had the genetic inclination to buy a cookie-cutter “contemporary” 3bd 2.5ba home in a neighborhood filled with nouveau riche neighbors with tonally equivalent flesh. Jane lived in Vancouver.

We met via and exchanged endless amusing e-mails. Once we had exhausted our witty e-mail verbiage, we moved on to the harder stuff…cell phone calls. We scheduled to meet on a Sunday afternoon in late October around 5 p.m., walk around the city a bit, and then go to dinner. Just before 4 p.m., my phone rang. It was the building’s front door intercom system. I had just gotten out of the shower and Jane was at the downstairs door.

I said, “I’m sorry, I thought we said 5 p.m.”

“It is 5!” she chirped.

“No, it’s not…it’s 4…um, didn’t you set your clock back an hour last night?”

“Set my clock back? Why?”

Through the silence, I could hear plinks of water drops falling from my body onto the flagstone floor. Not a good start. Nevertheless, I buzzed her up.

Now, I’ve been in situations like this and I realize how difficult it is to extricate oneself from appearing idiotic. Jane, however, made no attempt to upgrade her image.

I hurriedly put on a pair of black slacks and a cobalt blue dress shirt. I opened the door. In dating, first impressions mean everything, or so I am repeatedly told. Jane would have nothing of that. She arrived in sweatpants and matching sweatshirt, make-up askew, and chewing a wad of gum so forcefully that I momentarily pondered harnessing her jaws as an alternative energy source.

She apologized for her early arrival while I finished getting ready in the bathroom. I checked my sarcasm and told her not to worry. Ten minutes later, we walked out the door to wander through my neighborhood, the Pearl District, then up to an Italian restaurant on 21st Street. While we walked, she told me about her friends, and how they were generally screwed up in some way or another…alcohol, drugs, parenthood at 18 and divorce at 21. I was willing to suspend my belief that their various maladies had also visited Jane. After fifteen minutes of chatting, I knew we had nothing in common, but I thought that I should make the best of this. As my friends later said, “Treat it as a learning situation.”

At the restaurant, I asked her if she would like wine with her meal. She said no and then detailed the previous night. She was with her friend, Bobbie (fake name here, too, kids!), who has a kid by her former husband. Bobbie was depressed, drinking, snorting cocaine—generally self-destructive. I empathized with an occasional “how sad” or swiveled my head back and forth. As it turned out, Jane didn’t want any wine because last night, she had had too much to drink with her friend. Yes, Jane took her best friend, the alcoholic, suicidal, drug abuser to a bar for her birthday. I asked her, “Why did you take Bobbie to a bar?” Jane said, “Well, it was Saturday night, wasn’t it?” My jaw dropped into my gnocchi. I ordered another glass of wine—for me.

Does it end there? Not a chance. It was at that uniquely surreal moment that a fully adorned, robed monk walked in and sat down at the table across from me, a stunningly beautiful young woman at his side. They had the most wonderful conversation, filled with laughter and thoughtful conversation. I couldn’t help but wonder to myself if vows of chastity might be the most effective means to attract eligible women, or perhaps my sex life had become so vacant that even a monk can get some, but not me.

As with all of my dates during this period, this one ended with a whimper, not a bang (ahem). We walked back to her car. After a couple of awkward moments, we quickly kissed, and she was on her way.

This was a milestone in my post-divorce life, and I would treat it as the hump I needed to get over. Surely better times lay ahead