Readers may have embraced these "obvious-isms," but I wasn't through with my own bad-boy run. I loaned my newly replenished savings to a live-in lover eager to start a business managing fellow stand-up comics. That enterprise bombed; so did our relationship.

My bank account once again decimated (eight years later, I'm still waiting for repayment), I still didn't question my taste in men. After all, talk shows were calling Woman's Own to seek my input on topics such as "My Fiancé's a Flirt."

I was a natural, from the beginning. I would spend mornings distraught over a promising date that had morphed into a silent phone, yet once the TV-camera lights glowed, I'd quip, "Crying over a man who doesn't appreciate you is as wasteful as buying retail. Cut your losses and go for the true bargain." I wasn't sure what that meant, but since my host would chortle appreciatively, I came to realize it wasn't the soundness of the advice that mattered, but its entertainment value. After one Good Day New York appearance, in which I was introduced as "Sherry Amatenstein, relationship expert," a former boyfriend's mother, chancing upon the program, scoffed, "Expert? That's David's ex-girlfriend!"

I rationalized that I wasn't doing harm because the dilemmas I "solved" were relatively lightweight. How much damage could I inflict telling well-meaning mamas on a "Mom's Pushing Me to Marry" segment to "butt out or risk creating reverse Romeo-and-Juliet scenarios for their altar-shy kids"?

But I craved integrity, and resolved never to exaggerate my credentials. When Montel came calling, I warned his producers not to let the irrepressible host call me a shrink; I was a "relationship writer." (I never voluntarily wore the "expert" tag.) The day before the taping, I received a 15-page fax containing preinterviews from the troubled guests. My stomach sank; this was tough stuff. (Dominica: "I don't want a boyfriend to be faithful; he'd want me to be faithful." José: "If my woman no be faithful, I sleep with her best friend.") The producers requested that I be "fun."

Borrowing from the shrink Bob Newhart played in his first TV series, I role-played with the couple: "To be more empathetic, you need to put yourself in the other's shoes. Dominica, pretend you're José, who values fidelity. Now imagine how he'd feel to discover his woman had cheated …" I was cookin'—until Montel scolded his rambunctious studio audience to "Let the doctor speak."

In the sudden hush, I winced, then thought, "Mom wanted me to marry a doctor: I hope this will satisfy her."

"Doctor" label aside, that escapade left me feeling queasy. Helping couples cope with possible infidelity could have infinitely more toxic consequences than advising women whether or not to pay on a first date—especially since Montel's "aftercare" consisted of my delivering a five-minute post-taping consult in the dressing room.