Love Notes

Iris Levenberg and Dennis Bailen at their home in Libertyville January 4, 2013. (Dave Shields, for the Chicago Tribune)

When Iris Levenberg found herself divorced and living in South Florida in her 50s, the executive head hunter-turned-life coach was determined to find a life partner.

"I was on a mission," recalls Iris, now 61. "I spent years as a head hunter, and that's how I look at life: You're constantly searching for talent. I knew what I was looking for. So I went online and put myself out there. You can't expect things to land in your lap."

Meanwhile, Dennis Bailen was licking his wounds in the Chicago area after two divorces and 10 years of trying to find companionship online.

"Online dating is exhausting," says Dennis, 64. "It becomes a full-time job. And there were so many disappointments. I went on and off those dating sites because I hadn't found someone who really met my expectations. But I got tired of being alone on weekends, so I went back on JDate (an online dating site for Jewish singles)."

Iris immediately spotted Dennis online and viewed his profile not once, but twice.

"You notice when people view your profile," Dennis says. "But she lived in Florida, so that wasn't realistic since I was in Chicago."

A dialogue began a couple of days after that second viewing, regardless of distance.

"We got on the phone May 13 (2005), and we had a very easy conversation," Dennis recalls. "At the end of it, Iris said, 'This didn't seem like an interview at all!' After dating for 10 years I learned not to have expectations, so I was really happy it went so well."

Iris had family in the Chicago area, and a date was set for them to meet Memorial Day weekend so Dennis could show her around the city.

"I didn't know this at the time, but she had set up multiple dates when she came to town," Dennis says.

"And a job interview," Iris admits. "I wanted the trip to be worthwhile."

Dennis went to pick Iris up at Union Station, and his timing was perfect.

"Literally, I was pulling up to the entrance of Union Station, and she comes up the steps," he says.

"And you were listening to Joe Jackson music, and I remember thinking, 'Good taste in music.'" Iris adds. "He looked like his picture; I liked the way he dressed. I was relieved."

Their stroll along Michigan Avenue was a success, which led to a second date at Arlington Park race track the following day.

"We put $2 bets on every race," Dennis says. "We don't know horse racing; we bet colors, middle names. And we collected on every single race!"

"Dennis saw this as a sign, and I got freaked out because this was happening so fast," Iris says. "I'd just met him. And I still had four dates lined up."

Two days later, they planned to meet for dinner after Iris' job interview.

"I had canceled a couple of my dates. Not all of them," Iris says, much to Dennis' amusement. "And I was sitting on a chair talking to Dennis after my interview, and just talking to him was so easy — I decided to cancel my last two dates."

Later that night at the restaurant, they shared their first kiss.