Date #5: Much Less Painful Than A Root Canal

When I first learned that my date was a dentist, I have to admit - every negative experience I had with a dentist came flooding back. The dentist who called me a 'baby' for crying during my post root canal crown replacement. The amount of money I had to pay out of pocket for said 'root canal' for not having insurance at the time. Steve Martin maniacally drilling and singing "I am your dentist" in the movie version of 'Little Shop of Horrors'. Based on my own experiences, I fully expected 'this' dentist to be cocky, mean and certifiably nuts. I mean, what kind of person wants to be a dentist anyway?

Thankfully, none of the above traits came close to 'this' dentist.

We were matched on eHarmony and after going through the 'Five Phases of Communication' we were emailing and talking on the phone. I found him to be hysterically funny and easy to talk to. He's from Denver and complained about the fact that when people meet him, they automatically assume that he must be this hard core Aspen Extreme skier. He can't ski. I sympathized with him, saying that when people find out I grew up near Detroit, they automatically assume that I'm this hardcore rapper and that I know all sorts of things about cars - or at least how to hotwire one. I don't even own a car. His voice had that Michael J. Fox as Alex P. Keaton quality to it - young, energetic and bright. I tried to picture 'this' dentist and in my mind I saw a boy in a suit with a labcoat over it - looking very Doogie Howser, DDS .

So, after three very enjoyable phone chats, we were planning our date. We decided to meet late on Friday for dinner. I had a few errands to run after work and was not going to be available until after 9pm. He lives downtown and offered to come up to my neighborhood, where I would meet him outside the El station. Since he just recently finished his year of residence at Northwestern - where he basically lived 24 hours a day - he had never ventured out of the downtown area. As is fairly typical in Chicago, the trains were running erratically. It took him nearly an hour to make a trip that should have taken half that time. As a result I was wandering the streets of Chicago for a good half hour waiting for him. I called him several times to check in, but since he was underground, his phone went to voicemail. When I finally did reach him, I apologized for the four times I called him: "I'm sorry for calling you so much, you must think I have A.D.D." And he said, "No, don't apologize - it was a great boost to the ego."

Finally we find each other - both starved, but relieved. First impression? Cute! He is the exact same height as I am (so it was another outing for the 'flats') and he does indeed have this boyish look about him. If I had to guess his age, I would've said 18- 20. He's 29. Almost immediately I had the distinct feeling he was checking out my teeth, focusing on my smile. When I called him out on it, he laughed and became slightly embarrassed: "I don't even think about it. It's a total subconscious thing. I look at a girl's teeth before I look at her breasts."

We end up at Uncommon Ground - I know what you're thinking - are there no other restaurants in this city?! But it's the closest restaurant to where we were, and I knew it would be quiet and the food would be good and I was introducing him to my neighborhood and - wait. I don't need to justify this to anyone. I love that place, and they love me and I will eat there every damn day if I want to. So there.

After chatting up our server Nathan, and a table visit from the manager Steve, we end up splitting a bottle of wine and several dishes. The conversation is non-stop. He's asking me all sorts of questions and truly expressing interest in me and what I have to say. I find myself wanting to learn more about him. What made him want to be a dentist? What was it like to go through his parents divorce when he was only five? How does he feel about having a gay brother?

I also felt this bizarre need to inform him of my dental history - to sort of tout my superb oral hygiene. In a rush, I tell him that I've only ever had one cavity and I floss every day. I did have a root canal but only due to an error by my orthodontist. However, I should point out that I do have a bit of gum recession, as a result of some over-zealous brushing. I wondered if I had a piece of food in my teeth, would he tell me? He said he'd not only tell me, but he carries a 'scraper thingie' with him at all times for such an emergency.

I tell him he has a great personality, and I mean it. He laughs and says, "Does that mean I'm fat?" We talk movies and music (He loves Christopher Guest movies and Tori Amos), our families, our eHarmony experiences and how we're finding life in Chicago.

The night flies by and soon my friends at "UG" are closing up. He picks up the check and after he signs his name, I ask if I can see his signature. I'm commenting on it, when I happen to glance at the tip amount that he's leaving our server: $7 on a $60 bill. Immediately I start to panic. There is no way we are leaving that paltry tip for our server. Especially here. I'll never be able to show my face again! I excuse myself to run to the restroom and while I'm in there I pull out a $5 bill. Maybe I can find Nathan, slip this to him and return to the table all without my date noticing a thing. But the door to the restroom is directly in view of our table and there is no way. I'm panicked. I squeeze back into my seat, with the $5 bill wadded up in my hand, trying to think of a different plan. Just then I notice he is scribbling something onto his receipt. "I don't know what I was thinking!" he says. "Did you notice what tip I had written down? I had left him $7. $7 on a $60 bill!! I waited tables for years while in school. I should be shot. I'm so glad I caught that."

Me, too.

I nonchalantly slide my $5 bill back into my wallet and find that I can breathe once again. We leave "UG", and I smile with relief, grateful that I will be able to return to my favorite place without the scarlet stigma of 'cheapskate' attached to me.

We walk back to my place and he comes up for another drink. He's commenting on how cozy our apartment is, he's looking at my pictures and asking questions about the people in them. I'm verymuch enjoying his company and he seems to be enjoying mine - but it's always so hard to tell.

It gets to be quite late and soon I'm yawning. I walk him out and we stand on the porch talking and winding down. He hugs me and we make plans to have lunch together on Tuesday, as he will be downtown at work. Suddenly this very confident dentist turns almost adorably boyish and awkward. "Ok, this is the part of the date that I'm not very good at...I mean, well, you know - saying goodbye at the end of the night and all that. How do we...um, I mean, do I-" I lean in and give him a quick kiss, to shut him up and put him out of his adolescent misery. "Ok," he says, "Well, good. That's...that's perfect. Good. Goodnight." He sort of stumbles down the steps of my porch and walks away, whistling.

Later, as I stand in front of the bathroom mirror, brushing (and flossing) my teeth - I think of him. Who knew that a dentist could be charming, funny, sincere and adorable? And while I may have negative past experiences from those dentists forever lodged in my psyche, I have to say I'm kind of looking forward to seeing this dentist again.