How to Talk to a Widower by Jonathan Tropper Page A

click of the switch when she powered down her brain and tossed her career, but as far as my folks were concerned, all was forgiven when she married the horseshit heir.
    Debbie, three years younger than us, seemed to understand from an early age that all of my parents’ hopes and dreams were pinned on her, and she didn’t disappoint. She was a straight-A student, the kind who whiningly appealed every less-than-perfect test score to teachers who ultimately caved just to shut her up. She graduated Harvard Law School with honors and is already on the partnership track at a Manhattan firm whose name generates instant nods of approval among those in the know. She has a spacious office with a view of the Hudson River, her own secretary, and textured linen business cards with raised silver lettering. Somewhere along the way, though, she discarded her sense of humor, probably because there would never be a test on it, and now her laughs are rare and her smiles often rushed and vaguely pained, which is a shame because she was a beautiful girl and smiling had always suited her when she was younger. She’s still beautiful, but now it’s the kind of beauty that comes with a barbed wire fence around it.
    Not cut out for the Ivies, I just barely scraped through the State University of New York with a bachelor’s in English, leaving me perfectly qualified to do absolutely nothing that would earn me a living. As far as I knew, there were no essay portions at job interviews, and, that being the case, there hardly seemed any point in trying. So while my friends all splurged on pin-striped Brioni suits and joined investment banks and hedge funds, I bounced around a few PR agencies, writing inconsequential press releases and getting fired for a wide range of corporate delinquency. At one agency, I decided that I was going to re-create my work cubicle, item for item, in my apartment. Every day I would steal office supplies, from Post-it pads and pens to staplers, secreting them out of the office like Tim Robbins and his tunnel dirt in
The Shawshank Redemption
. I brought a gym bag to handle the larger stuff, like the telephone and fax machine. It was the actual cubicle walls that would prove to be my undoing. There was no way to sneak them out, so I waited until after hours and then acted like I was authorized to be taking a cubicle wall down in the elevator. The security guard in the lobby was unimpressed, and the next day I had to sit in a conference room with the head of HR and my flabbergasted boss, Stephanie, watching my criminal enterprise on the building’s surveillance tapes.
    â€œI can’t believe that’s you,” Stephanie said, looking away from the surveillance video.
    â€œThe camera adds ten pounds,” I pointed out.
    â€œDoug,” she said miserably, and I could see she now regretted even more having slept with me after a late client dinner a few weeks earlier. She’d worn her heels to bed and commanded me to slap her ass while she rode me like a cowgirl. In the morning she went through all five stages of grief before breakfast and then made me swear I’d never tell a soul. Then, since we were already there, we had sex again, to seal our pact.
    â€œYou know I’m going to have to fire you,” she said.
    I was actually kind of relieved, because my plan to steal the copy machine was proving to be a logistical nightmare.
    I had to return everything, but not before I photographed the cubicle I had so painstakingly re-created in my living room. Then I wrote a funny little article about it, which I sold to
M Magazine,
and that’s when I discovered magazine writing. I got myself an agent, a high-powered little blowhard named Kyle Evans, who sold my stuff and ultimately landed me a gig at
M,
where I wrote a fairly popular column called “How to Talk to a Movie Star,” a loose, comic riff on anything remotely connected to the Hollywood zeitgeist. Plastic surgeries and