Love for Life: Meredith and Jon Sinclair

Their story could be an American fairytale.


Blonde, perky cheerleader meets tall, handsome basketball player at a small-town high school in Pennsylvania. They fall in love and live happily ever after. They have two children, Truman and Max, and have been married for 20 years.

When they first got married, Jon explains, “We moved to where we knew no one. So we were really forced to hang out with each other.” He adds, “That’s never gotten old for me.” And when you’re with them, you instantly understand what he means. They banter, they flirt—genuinely enjoying being together.

And as befits the fairytale, both are successful. Jon is an executive vice president at Harpo Productions, and he’s worked for Oprah for 16 years. Meredith is a writer and blogger for Chicago Parent and has her own website

They’re also popular on Twitter, where their flirty interaction has over 11,000 combined followers.

“Back in the day, we got two-way pagers, like beeper 2.0,” says Jon. “We had those ten minutes and it turned into, ‘Hey, baby … ’ ”

“It’s cheeky and flirty,” says Meredith of their communication evolution from beepers to Twitter. “Now it’s a really fun way to keep in contact with each other during the day.”

And when they describe their schedules, it’s clear that keeping in touch through technology is part of what makes their relationship work.

“With Jon’s schedule, we never have family dinners,” Meredith says. “I felt really bad about that, but we adjusted our reality. We have family breakfasts.” Jon adds, “You can have the same kind of conversations over pancakes as you can over pot roast.”

And even with the crazy schedule, there are some definite advantages to having a spouse working for Oprah. “I give better gifts, I listen better, I know how you all work,” says Jon, who has worked on thousands of Oprah episodes with a staff of mostly women.

“I can’t get away with anything!” Meredith says with a laugh. But Meredith didn’t use Jon’s contacts or access to launch her blog. Instead, she found her own path to success. Like her adventure last winter driving a Mercedes-Benz SUV to the Super Bowl, as part of a social media promotion. “She’ll call me and say, ‘I’ve got this crazy idea … ’ and it usually works,” Jon says.

They might not work as business partners, but as life partners, the two are definitely in tandem.

“I bring him out, and he grounds me,” says Meredith. Jon adds, “Without us getting together I don’t see how any of this would have happened.”