Dear Coach Ken,
My name is Josephine Goldberg. I’m a 44-year-old single woman in Laguna Niguel, California, working as an entertainment reporter for The Hollywood Times and a licensed real estate broker. My Russian-Jewish upbringing shaped my belief in traditional courtship—a man shows serious intentions through generosity, effort and commitment.
After I interviewed you about Season 1 of your Tubi show, you advised me to look beyond chemistry and focus on mental compatibility. I tried your advice.
Recently I ran into Beverly Hills plastic surgeon Dr. Michael K. Obeng at Petros on Sunset. We’d had a falling-out years ago because he didn’t want to court me formally, and I didn’t want a purely physical relationship. Instead of reopening that argument, I told him about my interview with Gugu Zuma-Ncube, executive producer of Netflix’s The Polygamist.
To my surprise, he knew her, and we found an intellectual connection talking about the show, culture and relationships.
Then things got flirtatious—he put his arm around me, hugged me and kissed my neck. The chemistry was still there. I find him handsome, brilliant, accomplished and seductive. I’d never dated a Black man before him, and this attraction surprised me.
Could he take me to dinner and then “take me to the sheets”? I can imagine it. But then what? Five years ago I wanted the passion too—what I didn’t want was intimacy without a future. Casual relationships that leave me emotionally unprotected can trigger anxiety and depression. I want intimacy to be part of something meaningful, not a dead end.
Before leaving, I told him I hadn’t turned him down for lack of attraction. I explained I want commitment—ideally a ring, marriage and a family—and genuine support for my television career, just as I’d support a partner’s ambitions. If we don’t want the same romantic future, I’d rather remain platonic friends. From our conversation, I understood he doesn’t want to marry again.
So here’s my million-dollar question: Is there a win-win here, or are we still at square one? We share friends and professional circles—I don’t want to revive old conflict or alienate people we both know, but I also don’t want to compromise my boundaries just because a powerful, attractive man makes my heart race.
Am I being unrealistic to think two people with different expectations can meet halfway? How do I distinguish a genuine second chance from a return to chemistry without commitment? And how can I remain open to romance without feeling used?
As you prepare for Season 2, I want to revisit the advice you gave me during Season 1. I tried changing my mentality. Can that change the outcome—or is walking away the wisest decision?
Because when it comes to love, sex, money and second chances, decisions are never black and white.
After speaking with Coach Ken, I understand that at today’s market value, Dr. Michael K. Obeng and I are platonic friends. But as a businesswoman from a family of entrepreneurs, with a Jewish heritage of pioneering and looking toward the future, I believe people evolve—and so do their wants, needs, and desires. Darling, today’s terms and conditions aren’t necessarily tomorrow’s! I’m a businesswoman, not a psychic, and I’m always willing to review a revised offer.
Now, Dr. O is a brilliant, charming man, and I’ve seen many sides of him. Did he flirt, make promises, and play a few games? Let’s just say he knew his way around the negotiating table! But he never went all in. I believe that if he’d truly wanted to close the romantic deal, he could have made a stronger offer. Perhaps that’s why I still value our connection: for all the twists and turns, we never ended up in a romantic transaction that left me with a broken heart. And Dr. O isn’t the only gentleman I’ve shared a special connection with. Some men become romances, some become friends, and some remain part of the story. After all, I’m a real estate broker—I know the difference between someone touring the open house and someone ready to put down earnest money!
There’s a saying often attributed to Tyler Perry: “If your phone ain’t ringing when you’re struggling, don’t answer it when you’re winning.” Well, Mr. Perry, with all due respect, I beg to differ! Tyler Perry might not answer, but Josie Goldberg will—if the gentleman on the other end has a better offer and improved terms and conditions! I’m not lowering my standards; I’m simply willing to review a revised offer. And who knows? Maybe Dr. Obeng will sponsor a booth at my Spoiled and Entitled Celebrity Gifting Suite in Honor of the 84th Golden Globes, showcasing MiKO Plastic Surgery and helping my fabulous VIP guests keep Hollywood glowing. He may not have put down the earnest money for romance, but perhaps he’ll put down a deposit for a booth! Hollywood may age, darling, but that doesn’t mean we have to look our age. I’m Spoiled and Entitled, the exception, not the rule—and Only Josie Knows!
Josephine “Josie” Goldberg
Entertainment Reporter | The Hollywood Times
Only Josie Knows
