Connecticut College Magazine · Fall 2005


Mach Arom ´89: Rebuilding hope for Thai tsunami victims

Kathryn Bard ´68: Somewhere in Egypt

Who cares about Haiti?

Venturing into Iran: Beyond the warning

Gloria Hollister Anable ’24: Into the deep

Gaida Ozols Fuller ´74: Six months in Uganda

Sarah Trapido ´08: Going 13,000 miles on veggie oil

Yoko Shimada ´99: Fighting the war on AIDS in East Africa

The extra mile: Journeys that make a difference

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Ask him anything

Ask him anything
Rapper Snoop Dogg with Jonathan Small ´89 and Don "Magic" Juan. Yes, those are real diamonds on the cups!

Improving male-female relationships, one answer at a time

by Mary Howard

“Admit it: As great as men are, we can also be pretty damn frustrating at times — and nearly impossible to decode,” writes Jonathan Small ’89, in his “Ask Him Anything” advice column in Cosmopolitan magazine. Each month, Small, a Los Angeles-based freelance writer, answers questions from Cosmo’s readers, giving his “guy perspective” on their dating dilemmas. Small has heard everything, from the woman whose man drops his trousers in public after a few cocktails to the more typical complaints from women with commitment-phobic boyfriends.

While most of the questions and answers are humorous, Small takes his job seriously. “I have a responsibility to these women, some of whom don’t get advice from anyone else — which kind of scares me,” he says. If questions deal with serious matters — like alcohol, drug or physical abuse — Small will call a licensed therapist or M.D. to get a professional opinion.

How did this 38-year-old (who is happily married with a new baby) become Cosmo’s guy guru? “I seem to have a knack for giving good advice — but following my own advice? Not so much,” he says.

A history and theater major at CC, Small began to consider a career in writing after taking a fiction-writing class with Writer-in-Residence and Professor of English Blanche Boyd. “She was an inspiration. Her creative journalism class changed my life.”

After graduation, Small moved back to his native New York City and took a job as an editorial assistant at Child magazine. A stint as senior editor of Fitness magazine followed, and, as the only man in the office, Small edited a column on sex and relationships.

When Small was asked to pen a freelance story, “The XOXO Files,” for YM magazine, “All hell broke loose,” he says. Soon offers began to pour in from other women’s magazines. “I found a bizarre niche writing about relationships from a guy’s perspective,” he says. Small, who says he adores women, went on to become senior features editor at Glamour, where he served as the magazine’s “Jake,” writing “the holy grail of advice columns.” He later jumped to the other side of the aisle as executive editor of men’s magazine Stuff, where, among other duties, he doled out dating advice for men.

For the past five years, Small has been the anonymous (shhh! don’t tell anyone) author of Redbook’s “Diary of He,” a fictional column about Zach, a single magazine editor, who lives in New York City. “Zach is a dog. The column is sort of a ‘Sex in the City’ from a male point of view,” says Small. He admits to enjoying taking on the voices of Jake, Zach and Cosmo’s guy guru.

“These guys are never me, but more of an amalgam of single men I know,” he says. “It makes people laugh when they meet me. I really am sensitive to a fault — I swear! I cried during ‘March of the Penguins.’”

This is not the first time Small has had an alter ego. Alums from the mid- to late-1980s may remember him as “Kid Finesse,” deejay of the popular hip-hop show, Finesse Radio, on WCNI. At the time, there was no other station playing urban music in the area, and Small had a large following among the young people in New London. “They would stop by the station to meet me, and they were always shocked to find out that ‘Kid Finesse’ was really a skinny, white, Jewish guy from Westchester,” he says.

A resident of Los Angeles for the past three years, Small, who still considers himself a New Yorker, has created “quite a nice life” for himself. He has co-written a book, The Best Places to Kiss in Southern California, and has another book deal in the works that is based on his columns. And, in addition to gigs with Cosmo, Redbook, Marie Claire, Maxim, Blender, Teen People and Stuff, he does a fair amount of celebrity profiles, including stories on California governor Arnold Schwarzenegger, Pamela Anderson and Jennifer Lopez (who kept Small waiting in Miami for four days before the interview.). One of his favorite celebrity interviews was with rapper Snoop Dogg. “The guy just oozes coolness from every pore of his being. I got a contact high being around him.”

But profiles on average folks in unusual circumstances are what really interest Small, like the story he wrote on a West Palm Beach man who became a woman then became a man again, or the entrepreneur in Northern California, who started a crime-scene cleaning business. “He gave me tips on how to get those pesky blood stains off the carpet,” Small says. “I really appreciate good advice.”

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