So heartbreaking. Dennis Shields, who has been romantically linked to Real Housewives of New York star Bethenny Frankel, was reportedly found dead in his Trump Tower apartment on Aug. 10. The on-again, off-again couple met nearly 30 years ago, but didn’t start dating until 2016, and we’re taking a look back at their relationship over the years. 

Bethenny and Dennis first crossed paths when he dated one of her high school friends, Jill, who he later married. The reality star ended up not really staying in touch with her classmate, but she did have the same group of friends as Dennis. Several months after he separated from his wife, sparks began flying between Bethenny and Dennis in 2016 and they started dating. The Skinnygirl Cocktails founder later explained their connection while appearing on Steve Harvey‘s talk show in May 2018.

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(Credit: Getty Images)

“I’ve been with someone on and off for years,” Bethenny explained about their complicated relationship. “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. We’re trying to really kind of be good partners and be good teammates and I think relationships oddly are — and this sounds cold — but a little bit like business. If both people aren’t happy about it, but slightly uncomfortable and giving up something or giving in [to] something, it doesn’t work.”

Bethenny and Dennis began dating three years after she finalized her divorce with Jason Hoppy, and her relationship with Dennis was showcased on RHONY. Even though they’ve broken up several times, Bethenny and her loved ones hold a special place in their hearts for Dennis. “Bethenny and her daughter Bryn love Dennis and his family and they have been a support system during her negative divorce and a positive influence in Bryn’s life,” a source previously told People. It’s unclear where Bethenny’s relationship stood with Dennis before his passing.

Jill has since broken her silence on Dennis’ untimely death. “We are all heartbroken. Dennis was, and will always be, the love of my life,” Jill said in a statement to People. “His spirit lives on in our children. Please respect our family’s privacy at this time.” Dennis reportedly requested his assistant administer Narcan for a prescription pill overdose before his passing, but it was too late, according to The New York Post. He was pronounced dead around 9 a.m. EST at the age of 51. Our thoughts go out to his loved ones during this tough time.