Through four years of college Louise Holmes was always in my dreams and always out of my reach. So you might imagine the huge surge of adrenaline when one Friday afternoon, two years after graduation, I obeyed the DON’T WALK sign at 53nd and Broadway, looked to my left and discovered she was standing next to me, little changed. “Hi,” I said.

Which was the closest I ever got to dating her during college. That lost chance always irked me, but the greatest regret I have was the first time I met her. It was my first class of my freshman year: ‘COM 107: Communication and Society’. It was 9am and I had been up too late with friends the night before watching the Audrey Hepburn, Humphrey Bogart movie Sabrina. Drowsily, I sat sipping Dunkin Donuts coffee and waiting for the professor to turn up. When this beautiful girl, a brunette with deep mahogany eyes was standing next to me. The nauseating, thrilling spread of excitement exploding in my stomach snapped me awake.

She carried a sports bag from which a tennis racquet awkwardly stuck out of. She asked if I could help with her bag. Of course, I did. She said she was embarrassed about wearing the outfit but explained that she wouldn’t have time to change after class before playing. I looked at her again, she wore a white Tennis mini-skirt and top, shrewdly enunciating her figure and presenting her lightly tanned legs. I didn’t believe her for a minute.

But it took me too long to understand what happened in the hour that followed. There was a little glance we gave each other when we repeatedly got told off for talking through the whole lecture. There was the way she playfully hit me once or twice. But more than anything it was what she said as she was leaving: “Do you play Tennis?” “No,” I said. “It’s an easy sport to learn.”

I didn’t think anything of it at the time. Half an hour later I realised it had been an invitation. In the years after, whenever I would resolve to ask her out I’d discover she’d be dating a football player, a lacrosse player or a drunken jerk. Occasionally all three in one. We’d sometimes bump into each other through mutual friends but nothing more. We’d just say ‘Hi,’ maybe a few pleasantries and move on. I have always truly regretted how I reacted in that first moment.

And on this otherwise average Friday afternoon she was standing next to me, stopped by the DON’T WALK sign. The shiver of opportunity felt the same as my first day of class. “Hi” she glanced at me and stared straight ahead, she was willing the sign to change. She got this a lot. I said; “James Lane. You don’t recognise me do you?” She looked at me.

There was a flash of recognition. “Oh my God! James! Yes! How are you?” “Great. You?” “Fantastic. I’m living down in Soho and working on the Letterman Show. I love it. What’d you end up doing?” “Music video production. A company down on 28th. Probably not made anything you’ve seen, but itÕs fun all the same.”

We talked mainly about her time in Europe. She then said she was going away for the weekend to the Hamptons and she had to get home to get ready but it was good to see you. If you’re around I’ll probably bump into you again.” “Good to see you too,” I said.

I’d lost her in the crowd before I realised I’d done it again. I didn’t even have her number. All I knew was that she worked for Letterman, but I also knew there was no way of getting in there. The two huge security men on the door are men you don’t argue with.

The only way we were going to talk again was if I bumped into her. And what are the chances of that?

Well, that depends on where you are.

I took a half day the following Monday and worked on the assumption she’d have the same routine every day. The same exit, the same streets, the same subway. I sat down with a subway map but there was too many possibilities to tell which train she took to Soho. If I didnÕt know which subway she was heading to, I had to catch her leaving work.

On that Monday afternoon, I walked up to the Ed Sullivan theatre at about three. An hour earlier than I’d bumped into her on Friday. I took about ten minutes to look for a good place to sit where I could see the exit of the building. Eventually I found a spot to sit and watch from: the Dunkin Donuts opposite. I got an iced coffee and stared intently out of the window. Woody Allen has been quoted as saying that ‘80% of success is turning up.’ I planned to turn up each day until I saw her again. I felt like James Bond. I probably looked like a lunatic.

I stayed until 7pm. And by 7pm I didn’t feel like James Bond any more. That day gave me a new respect for police and stalkers. You need a determination and persistence I don’t have. One day of failure was quite enough.

A week later, a friend of mine told me that he had been delivering a letter to the Mayor’s Office for Film and Television and after being roughed up by security he bumped into David Letterman in the elevator, Letterman made a joke about the security guys. My friend explained: “The Film and TV office is in the Letterman building.”

The next day I took an extended lunch hour. I bought a legal size manila envelope, it looked thin on its own so I put a dozen blank pages inside. I took a printed label from my company and addressed it to “The Mayors Office for Film and Television.” I stamped it URGENT AND CONFIDENTIAL. I walked up to the guard at the Ed Sullivan theatre offices, who was talking to someone, he ignored me at first, I almost walked straight past him, but suddenly he looked at me. “Where are you going?”

“I’m just just delivering this to the Mayors Office for Film and TV.” He looked at me sceptically, I held up the manila envelope and he frowned, staring at me. Then he nodded me through. He told me the Mayor’s Office floor. But I still didn t know which floor for Letterman.

I went to the Mayors Office. There I told the secretary I had to deliver a letter to the Letterman Show and asked which floor it was. I went back into the lift and pressed the button. The doors opened revealing a large sign announcing: “The Late Show with David Letterman.” I walked over to the receptionist. “May I speak to Louise Holmes, please.”

Once again the nausea of excitement sparks to life as the secretary presses a button and speaks into the microphone on her desk. “Louise Holmes, please come to reception,” fills every office through the loudspeaker system. “She’ll just be a minute.” This is my second chance.

She appears through the glass door. “Hi,” she says, in slight surprise. The nauseating thrill spreads, tightening my chest, choking my normally coherent speech and I meander and fumble and babble until I eventually make it round to “so I was wandering if tonight you would like to have dinner, once you’ve finished?”

There is a pause as the nausea evaporates leaving pure adrenaline.

“Thanks but I’m really busy tonight. I have friends over.” “Tomorrow?” “Yeah. Then too.” “The weekend?” “Well, you see I’m going to stay in the Hamptons.” “Right. And next week you are…” “Really busy too.” She nodded and looked at me. There was another long pause, not flirtatious, we just had nothing to say to each other.

“Remember that first day of class?” she asked. I nodded, smiling slightly at the memory but more the fact that she had remembered it. She said: “A shame you didn’t play tennis.”

She looked for my reaction. She said, “See you around.” But it was clear there would be little chance of that. I left the building and threw the manila envelope stuffed with the blank pages in the trash outside the door.