Jack and I met on MySpace. He stumbled across my profile. We started talking, and I agreed to meet him for lunch on January 1, 2005. I thought it would be promising to start the year off with a date. Wasn’t that a great sign of how the year would be?

He picked me up in his truck. We went for Thai in Silverlake. Jack was a gorgeous, well-built, quiet and mellow singer-guitarist. I was a gorgeous talker (still am). We’re sitting there, two good-looking people. The sexual chemistry was there; there would have been fireworks if we’d made love. Unfortunately, all the other chemistry wasn’t. I did most of the talking on this cheap date. Neither of us was suffering through the date, we were just different types of communicators. He’d actually smoked pot before the date. When I told him I didn’t smoke, he shrugged it off. After lunch, he dropped me off at home. He went off to watch The Rose Bowl.

Two days later, he called me. I returned his call and left a message. He called me back eventually. I carried most of the conversation. We didn’t make any plans. We hung up. That was it. There was nothing to pursue. Shortly after, he changed his MySpace relationship status to “In a Relationship.” Then, he removed me from his friend’s list.

Eleven months later, in December, I got a message from him. It read simply, “Can I get a do-over?”

This had never happened to me. I wasn’t sure what to say. I was pretty damn annoyed by him, and I really had no interest in being rejected twice. Since the new year was approaching, with no real intentions of ever meeting him, I replied, “Yeah, sure. How about we get together January 1st? I’m starting this thing where I date a guy once a year on the same date every year.” He replied, “Okay.” I didn’t reply. We didn’t together. I went to Chicago instead.

(Jack and I share a love of Mr. Withers. I like to think he was missing his dose of sunshine when he asked to see me again. ;))

We exchanged a few more messages, and over the months, I lightened up a little and genuinely intended to meet with him again. However, there was that part of me that sincerely didn’t want to give him a do-over or see him again. I hadn’t changed, so would he meet me again and be reminded of why he stopped calling in the first place. Our meeting didn’t happen.

Then, in the summer of 2006, I was working out at the gym regularly during lunch. I walked in and there he was. He looked better than I remembered. I was instantly attracted to him again. The last and only time I’d seen him in person was on New Year’s Day 2005. We had a short chat. I asked him why he was working out in the valley when he lives in West Hollywood. He reminded me that he worked in the valley. I never returned to the gym at that time.

A few months later, I took a promotion as an advertising executive for the newspaper where I worked. This is when I began to realize just how small Los Angeles is. In February 2007, I had thrown a party for one of my clients (The Sex That Got Away #10) and his employees in a suite at an L.A. Kings game. I invited one of my co-workers, Barbara, who had been my client’s advertising representative at another paper. She and I took a picture together. I posted this picture on MySpace because Barbara wanted her son to see just how cool his 60-something mom was.

A few days later, Barbara entered the office and said, “Jack says hello.” “Jack who?” “Jack Wright.” I asked her how she knew Jack. She explained that Jack had seen our picture on MySpace, called her, and wanted to know how she knew me. It turned out Jack was the manager at a spa and hot tub company in our market. She was his advertising representative at another paper. He was actually currently advertising in my paper with another representative, and I had no idea. And there Jack was back in my little world.

I began to seriously think maybe I need to do this. Maybe I need to give Jack the do-over he’d asked for almost a year and a half earlier. I believe everything happens for a reason, and wasn’t this coincidence something. I am a romantic person. Maybe this was all supposed to be a part of the story Jack and I would tell our grandchildren. I just knew there had to be something there. This had been going on with this guy for two years. Two years! One date and still this. We picked up our communication again sending messages; a few were exchanged, and nothing. Again. I didn’t want it.

Then on May 5, 2007, my friends and I went to a Mexican bar to celebrate Cinco de Mayo. They all arrived a while before I did. As I walked through the bar looking for them, I saw Jack sitting with two friends drinking beer. I couldn’t believe it. Of all the bars in L.A. to celebrate Cinco de Mayo, he had to be sitting in mine. We didn’t go into extended hellos. I said hi and kept walking. We both stole a few glances while at our separate celebrations, but nothing more.

In the winter of 2007, Jack called to tell me he was moving to New York City. He had had enough of Los Angeles and wanted to give his music a shot in the City. He wanted to see me before he left. I had a feeling this was a last ditch effort to get me in the sack (they happen to me often). That’s what I wanted it to be. I had just ended a relationship, and was horny. I got his personal email. I said I’d write. I said I’d call. I never did.

Ultimately, Jack was the first person to go out on one date with me, reject me, then come back. Since Jack, I have suffered much worse rejection; painful, gut-wrenching rejection. Jack’s rejection was like eating a slice of blueberry pie on the beach compared to the rejection that was to come. I’ve also had a few requests for do-overs. I haven’t handled them all that differently than this one for many of the same reasons, but I mostly declined because I’d completely gotten over the guy.

If Jack reached out today, I’m 100 percent certain I would meet with him. He knows how to find me. I know how to find him.

K.