The Best 20 Bucks I Ever Spent

My divorce from my second wife was finalized in May of 2003.

We'd separated in February, 2002. For a few months after my separation from her, a woman I'd been involved with when I was 18, during my first year in college, dropped into my life. She was also in the middle of divorcing her second husband. The relationship started spinning its wheels and flickered out. I made the decision that I needed to take a break from relationships for a while and figure out why there had been two divorces.

By the fall of 2004, I felt like I was ready to start dating again. I'd come to realize that I was always looking for my relationships to make me happy. The fact of the matter is that you need to get yourself into a good place and then you're ready to find love.

I was in a job I loved. My kid was doing well-- he was done with the anger and confusion he'd felt when his mother and I were dealing with custody through a cold, stupid court system. I was living in a neighborhood I loved, and was surrounded by a group of friends whom I'd been with near on 20 years.

I didn't know how to start even. Hanging around in bars was out-- I was a little long in the tooth for that. Being a teacher, there were single women around, but they were way too young, and I'd learned the hard way when I was younger about dating someone you work with.

I decided to try the singles ads in the Reader, the local "free" newspaper. It was a pretty good deal-- twenty dollars a month.

I discovered that they were now mostly online. I was intrigued. I spent a long time figuring my ad out. I wanted no more failures. I wanted whatever prospects there were to know upfront what I was about. Left politics. Books. Red wine. The New York Times. Caffeine. I have a kid. Travel. Tom Robbins. Punk rock.

I wanted to make sure whoever I met had a sense of humor, so the picture I used was the very one at the top of this blog. It was taken in 2002, in Shanghai, China.

I began getting responses to my ad. With this newfangled system, you could send messages and "flirts" and such. After a number of emails back and forth with people, I finally had a date.

We met at popular middle eastern restaurant in Chicago's Andersonville neighorhood. Things started out pleasantly, but I soon realized that she was not a very happy person. And not too sociable. I was once described as "The most sociable man in the universe." I needed someone who could stand up to me.

I realized that I was slowly becoming more interested in watching the Red Sox making their run to the World Series on the televisions in the restaurant than I was in the date. We finished dinner, and I gave a polite goodbye.

Date #2, I felt, had some promise. The woman was extremely outgoing, working as an actress, including work with Chicago Public School students. I thought we'd have lots to talk about.

We burned up the email lines and talked a couple of times on the phone. We agreed to meet at a Thai restaurant nearby for dinner.

Fifteen minutes into the date, she suddenly stopped talking. We finished dinner and never talked again.

I had one psuedo-date with another woman-- we ordered food in and watched a movie at her place. We chatted on the phone a couple of times, but I realized that she was chronically depressed, and was not over her ex-husband yet. We never went out again.

I was nearly ready to give up. I had two more dates lined up. One was with an artsy latina, and the other with a single mom from Minnesota who'd been divorced for about as long as I had. I'd already made plans to have a drink with Ms. Artsy for a Sunday night. I had been trying to arrange a date with the single mom for a week-- with schedules with our respective children and my second job, it was difficult. She wanted to go out that Sunday, but I'd made plans already. We decided to go out the next night; her daughter would be with her ex- that evening.

Ms. Artsy was a tall beauty. She was educated-- intelligent, easy to talk to. We had to change our plans-- the wine bar we had planned to was closed on Sunday. We went to Quenchers and ordered a bottle of wine.

Things at first went well. Then she launched into a long talk about her life of dysfunction-- cocaine and heroin use. Cheating on her husband. Sleeping with college professors. Sleeping recently with her equally dysfunctional neighbor. Wow. All on the first date. What was waiting for date #2? I regretted not going out with the other woman.

Fortunately, I had another chance the next evening. It was still a scheduling nightmare. We'd picked out a restaurant-- the Tango Sur, an Argentinian restaurant on Southport avenue. It was "BYO," so both of us planned to bring a bottle of wine. She ended up getting out of work late; I was a little annoyed. I hate being late, and hate when others are late. I understood, though.

We met up in front of the restaurant. When she walked up, I could tell I was in trouble. She was tall and pretty. And her eyes were full of mischief. And I'm a sucker for tall, pretty and full of mischief.

Dinner was wonderful. We headed out for a drink afterward. We talked for maybe 5 or 6 hours that night.

About half an hour into the date, I had stopped her and said "We're going to have a second date, aren't we?"

We had a second. And a third, fourth and fifth.

After we'd been dating for a time, we went to a party some friends of ours, who own a record store have every summer. We brought our kids with-- each of us had one child. We met a friend of theirs, a guy who owns a local gourmet coffee company, and his wife. He and his wife had met through a dating service-- a pricey one. He related his tale of being sent on bad date after bad date. He smoked, and wanted to meet someone who smoked. They kept sending him women who didn't smoke-- and were depressed as well. Part of his service was counselors who consulted him personally. They asked how they could improve their service. He testily told them that it would help if they would stop sending depressed women who didn't smoke!

They apparently obliged-- his wife was smoking away, very cheerfully.

He told us that he'd spent $5,000 in his search, and asked us how much we'd spent. Kim and I looked at one another, chuckled, and told him "Twenty dollars. Each."

On December 30, 2005, Patti Smith's birthday, we got married at our friends Greg and Christina's apartment, overlooking Lake Shore Drive. Our kids were there with us.

We celebrated our first anniversary recently-- apart, as it turned out; we were bringing our kids to see their families in other states for the holidays. But that's part of it all, one of the things that we share-- always putting our children first.

Happy Valentine's Day, doll. I still feel like it was the best twenty bucks I ever spent.