Ray Dudgeon Goes On A Date. . .

Excerpted from BIG CITY, BAD BLOOD by Sean Chercover

As I drove along Clark, it occurred to me that Jill might be intending for me to stay the night. Everything seemed to be heading in the right direction. We enjoyed each other’s company and there was sexual chemistry in abundance and we’d come pretty close to naked on our last date. But Jill wasn’t sure that she could be in a relationship with a guy who carries a gun and disappears for days at a time and makes enemies of violent men. I was trying to convince her that she could and I seemed to be succeeding, if slowly.

We first met in the emergency room at Rush Presbyterian. She was a nurse and I was a guy with a black eye, a broken nose and two cracked ribs. I’d been working on a case for a chain of hardware stores. Merchandise had been disappearing from their distribution warehouse, so I went undercover in the shipping department and worked there until I knew the names of all the employees involved. I testified against them and they were convicted. But their fence, Pat Delany, was upset that I’d cut off a major supplier, so he sent a couple of hard guys to make me hurt. Which they did.

When you arrive at the hospital in such a condition, they automatically call the cops. Jill listened as I told my story to the two uniforms who responded to the call. After they were gone, she said, “Seems like an awfully difficult way to make a living.” To which I replied, “Would you like to have dinner with me?”

That was three months ago. My ribs still tingled sometimes but it had been worth it, just to meet Jill. She was smart and funny and pretty and had all the right curves in all the right places. She was sexy and she knew it and she wasn’t afraid of it.

And it went deeper than that. While we were moving slowly on the physical relationship, the emotional connection had developed almost immediately. On our second date, something just clicked. Something beyond sexual chemistry and shared interests.

Jill was working the night shift at Rush, so we met for a romantic lunch at a little Italian joint called Sotto Le Stelle. True to its name, the place had hundreds of little white lights set into the ceiling, which was painted to resemble a night sky with scattered clouds. The restaurant’s windows were tinted black and there were candles on the tables and it really did feel like dining under the stars. We shared a bottle of Chianti with our lunch and, as the waiter refilled our glasses, it struck me. Normally during the early dating phase of a relationship, you project an image of your best self. It’s a sales job, really. But this was only our second date, and it felt completely authentic. I didn’t feel like I was projecting an image of my best self. I felt like I was my best self. And I had the sense that Jill was feeling the same thing.

Walking down Armitage after lunch, Jill took my hand in hers. I glanced down at the swell of her hip and felt an erection growing. She stopped and kissed me softly on the lips.

“I want you to do something for me,” she said. “I want you to show me something in this city that is special to you.”

I took her to the Shedd aquarium, where we wandered the tropical reef exhibits. Jill had never been diving and asked a lot of questions about the animals in the massive tanks and artificial habitats. I pointed out the different sharks and rays and eels and schooling fish and corals. Jill held my hand throughout. She never asked why this place was special to me. It seemed enough for her to just know that it was, and to enjoy it along with me.

Walking back to the car, I said something funny and she laughed and I watched her face in the afternoon sun – her small ears, her sharp nose, the fine lines around her mouth and next to her eyes that would only deepen with time – and I was struck by a feeling so pure and so certain. I could see her as she would someday look, a woman in her seventies, and I could see myself, still walking with her.

I could see myself growing old with this woman.

And on the dates we’d had since, that feeling had only become stronger, but Jill was still uneasy about my chosen profession. Now, driving to her apartment, I was hoping that she wanted me to spend the night and at the same time hoping that she didn’t, because I had to meet Terry later. What the hell . . . if it came down to it, Terry could wait. Professionalism be damned.

And then I noticed the green Ford in my rearview. I’d spotted it outside the liquor store when I picked up the wine. Just a car with two guys in it, idling at the curb. Two guys who just happened to pull away from the curb and into the flow of traffic two cars behind me and who just happened to be following the same route to Lakeview. But that didn’t mean they were following me. When I stopped at the El Jardin Cafe the green Ford kept going and I put it out of my mind, determined not to be paranoid.

Now it was there again.