Breaking up after many years together is often a tumultuous ride. It’s a roller coaster of painful realizations, uncertain vacillations, and a lot of crazy behavior.

The craziest break-up I ever had was all that — and more. In fact, it almost derailed my career.

Only, it wasn’t my breakup.

(Put on your seatbelt, friends…because you’re about to go on another O’Brien expedition of wacky-but-true tales from the past.)

One day, I was sitting in my office cubicle at a highfalutin investment bank in Century City, minding my own business, when the phone rang. I picked it up and to my surprise it was my good friend Hannah on the line, sobbing uncontrollably.

The cube life. Don’t knock it ‘till you try it.

“Chr…Chri….Christen”, she said between sobs, “can you..taaaalk?”

Normally I didn’t take personal calls at work, but Hannah was a mess.

“Umm, sure”, I said hesitantly. “What’s going on?”

Hannah had been going through some rocky times with her boyfriend, Darren, after 5 years together. It was clear to me they were not a good fit, but of course that’s an easier conclusion from the outside.

“This morning, I went over to Darren’s apartment just to say hi”, she said. “He didn’t answer the door and since I have the key, I just went in. So I walked into the kitchen, and I saw the table set for 2. There were 2 dirty plates, 2 napkins, and 2 empty wine glasses. And there was lipstick on one of the wine glasses. Darren wasn’t there, but it was clear that…that…”

She sniffled. “It was clear that he had a date last night”.

“Oh jeez”, I said. “I’m so sorry. What are you going to do?”

“I think I’m going to call him and tell him that I saw everything, and its so screwed up, and how hurt I am. I mean, how could he do this to me after all these years? I still want to be together.”

Hannah started sobbing again. Hysterically.

She was almost wailing.

Right then, the other line started ringing. I had one of those old Nortel office phones that had more buttons than an F18 cockpit. Every time another call came in, one of the buttons lit up bright red…and that damn phone made me so nervous I would forget if I had to push “hold” before picking up the second line, or after. And if it was a call for someone else, it was even worse because I often hung up on people instead of transferring them.

“Oh, Hannah…hey, Hannah? Hold on just a sec, someone is calling”, I said in a panic.

I pushed the blinking red light. “Hello, Houlihan Lokey”, I answered, in my perfect investment bank voice.

“Hi, yes, I’d like to speak with Scott Adelson”, a woman said.

“Sure”, I replied. “Let me transfer you.”

I hit “hold”, I hit “transfer”, and then I typed in Scott’s extension. The light disappeared — meaning, it worked. I didn’t hang up on her…which was good because Scott was the Head Managing Director.

I hit the yellow “hold” light and went back to Hannah.

“Hi, sorry about that. So — I don’t think you should call him”, I said.

“You don’t?”, she asked. “Why not?”.

“Because — here is the thing about guys”, I told her. “They are the hunters, we are the gatherers. You shouldn’t chase him. Let him chase you! Calling him will send the wrong sign — you aren’t desperate! You need to be the strong one. Let him call you.

The line went silent. And then she replied:

“Why can’t I speak with Scott Adelson?”

My heart dropped into my stomach, as my hand involuntarily moved upwards to cover my mouth in sheer disbelief.

I’d just transferred my sobbing, wailing friend Hannah to Scott Adelson, the Head Managing Partner at one of the most powerful investment banks in Los Angeles.

And I’d just told a woman who most likely was a Fortune 500 CEO that she shouldn’t call a male business associate because… he should chase her.

Need to IPO? Or need to have a good break-up cry? Call Scott!

I quickly grabbed my co-worker, had her successfully transfer the call to Scott Adelson, and I excused myself for the day in fear Scott could somehow trace the call to my cube.

By far and away, Hannah & Darren’s breakup was the craziest one I ever had.

And needless to say, I never took a personal call at work again.