Bethenny Frankel and Dennis Shields: Look Back at Their On-Off Relationship

Bethenny Frankel and Dennis Shields knew each other for nearly three decades and dated for about two years before his death at age 51 on Friday, August 10.

The businessman opened up about his history with the Real Housewives of New York City star, 47, during his final interview. “I’ve known Bethenny a very, very long time. I met her when we were both still in college, and my ex-wife [Jill] and her were friends in high school,” he explained said on the Listen Up Show With Mitchell Chadrow on Sunday, August 5.

Bethenny Frankel and Dennis Shields
Bethenny Frankel and Dennis Shields www.INSTARimages.com

“We remained friends the whole time that I was married — nothing but friends. And then right after Jill and I got separated, Bethenny and I started dating,” he continued. “But we do break up a lot.”

Frankel, on the other hand, was a bit more shy about the status of her relationship with Shields, though he did make several appearances on her Bravo reality series.

“Dennis and I have a very independent relationship,” she said on the April 25 episode. “Everyone wants us to define what it is. It’s not definable. We love each other, but the two of us have schedules that are off the charts insane. I’m OK with it being totally gray.”

The Skinnygirl founder echoed similar sentiments on Steve Harvey’s talk show on May 9. “I’ve been with someone on and off for years,” she said. “It’s like a partnership where if we’re not being teammates and it’s not working and one man is down, then the other man is down.”

The couple’s romance was a hot topic on the RHONY season 9 reunion in August 2017, too. Frankel spoke about how she began dating the banker after she finalized her divorce from Jason Hoppy (with whom she shares 8-year-old daughter Bryn) and after Shields separated from his wife, Jill.

“A person that’s been married that many years needs to go through a certain cycle,” she told host Andy Cohen, referencing one of her brief splits from the entrepreneur. “I think that I needed him to make changes that I really didn’t think he would make, and I think that … the possibility of losing me really scared him straight.”

Shields was found dead in his apartment at Trump Tower on Friday morning. The cause of death is being investigated. The New York Post reported that Shields allegedly overdosed on prescription medication.

Sign up now for the Us Weekly newsletter to get breaking celebrity news, hot pics and more delivered straight to your inbox!

Want stories like these delivered straight to your phone? Download the Us Weekly iPhone app now!