How Attempted Blackmail Changed Jen Kirkman’s Life

The comedian shares an excerpt from her new book, in which a lost phone and a little wisdom from an undercover cop give her the confidence to make a drastic life decision.

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You may have seen Jen Kirkman appears on the talk show “Chelsea Lately”… or confusing Richard Dreyfuss with Frederick Douglass in the series “Drunk History.” Her new book is called “I Know What I’m Doing — and Other Lies I Tell Myself: Dispatches from a Life Under Construction.” She shares an excerpt with us, which you can read below. Or listen to her tell the tale in the audio above.

DPD-BannerJen Kirkman: Hi, this is Jen Kirkman, and this is a story about how losing my phone led to the end of my marriage.

So, I’m at Foxwoods Casino in Connecticut with my parents, and I’m gambling at the “Sex and the City” machine with my father, like most fathers and daughters do. I had been texting with someone the entire time.

Now, I was married at the time, and the person I was texting — let’s call him “Kevin” — this man and I were having what you would call, maybe, an emotional flirtation.

Kirkman - Book Cover

I had originally met Kevin months earlier when I went to New York City to do a comedy show. But Kevin and I had exchanged numbers and emails and I was telling Kevin every detail about how unhappy I was being married. And Kevin — who had been divorced himself — was telling me what the divorce process is like, and that now, he’s just a free spirit guy who lives in upstate New York.

Now, I had a trip coming up to New York City, and we were texting about it, and the texts were a little flirtatious, things like: “I’m not sleeping with you.”

“I know that, Jen. We just said we’d meet up for a drink.”

“OK, I’m just letting you know.”

And I wasn’t paying attention to the game, and then I left my phone somewhere.

So, I’m in my hotel room, and I decide, “Oh! I’ll just call the number, and I bet some nice, old lady who’s downstairs playing bingo will have it. And instead, a man answered, and I said, “Hello, who’s this?”

And he said, “This is Jose.”

And I said, “OK, well, this is Jen. I’m the owner of the phone.”

And he said, “Oh, I know who you are, Jen Kirkman. I know you from television.”

And so, I was like, “Oh, thanks for being a fan. And you know what? I’ll give you $50 for giving me my phone back.”

And he said, “$50? Well, you’re rich and famous. I want $5,000.”

Which, you know, in the grand scheme of things isn’t that much money, but when you have a joint checking account with your husband, suddenly withdrawing $5,000 doesn’t really fly. But I just agreed to meet Jose outside of Radio City Music Hall the next day and just figure it out.

So, I was having lunch with a girlfriend the next day, and I was telling her about my problem, and that I was freaking out, and I was going to have to tell my husband in the most awkward way that I wanted to end the marriage. And the reason that I had to tell him right now was because these messages were about to be exposed, but I wasn’t really having an affair, just sort of an emotional thing. And my friend said, “Wait a minute. The guy that works in my office building used to be an undercover cop. Maybe he can help us.”

He called two of his undercover cop friends, and so, we arranged to meet an hour before I was supposed to meet Jose outside of Radio City Music Hall to set up our sting. Now, when I met with these guys, I just saw them on the street, and I waved like a dork, “Are you the undercover cops?” And they walked into a bodega, and I followed them.

And talking between the food aisles, they were saying to me, “Don’t look us in the eye. Don’t walk near us. I will be standing in the lobby of Radio City looking at brochures. Undercover cop number one is going to be on the other side of the street. Now, Jen, you’ll be on this corner, and when Jose comes over to you, pretend to give him the payment. That’s when we want you to toss your hat in the air, and we’ll come out and handcuff him.”

So, it was like a bizarre, immoral “Mary Tyler Moore” opening credits scene. And so, I get there, and Jose’s not showing up, and after about 45 minutes, the undercover cops, they finally stood next to me, and they said, “The sting is over.”

So, I’m walking away with the two undercover cops. The main undercover cop — we had actually gotten to know each other a little bit that afternoon, and he said to me, “I don’t mean to pry, but there must have been something really important on that phone for you to go to all this trouble. What does your husband say about this?”

And I asked him, “How did you know I was married?”

And he said, “You’re wearing a wedding ring.”

And I was like, “Oh, right.”

And he’s like, “I mean, we are intuitive. That’s our job. You know, we have to go with our guts in certain situations.” And he said that with no sense of irony as he was adjusting his pants to make room for his actual gut.

But he said to me, “I know it’s not my business, but whatever’s going on, it seems like something that I can’t give advice about, but that you might need to follow your gut on.”

And after he gave me that advice, we kept walking with our coffees, and — I kid you not — as we rounded the corner, there was a homeless man sitting on a crate playing a saxophone. It was a perfect New York moment, and I realized that I did have to follow my gut. And when I returned home from New York City, I said, for the first time to my husband, “I don’t think this is working out.”



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