Bethenny Frankel's relationship with on-again, off-again boyfriend Dennis Shields is complicated

“[I’ve] been on and off in my relationship for so many years that I don’t love to get too into it in public, not because I’m hiding anything, more so because I never know exactly where it is, because it’s ever-shifting,” the Real Housewives of New York City star said during an interview with PEOPLE Now.

“I have a daughter, I had a very difficult divorce — I’m not legally divorced yet,” Frankel continued, referencing both her ex-husband Jason Hoppy and the pair’s 8-year-old daughter Bryn.

Celebrity Sightings in New York City - June 14, 2016
Dennis Shields and Bethenny Frankel
| Credit: Alessio Botticelli/GC

While the reality star has long resisted putting a label on the pair’s relationship, she first met Shields almost 30 years ago when he dated (and later married) one of her high school friends. Though she didn’t stay in touch with her classmate, Frankel and Shields share other mutual pals and began dating in 2016, several months after he separated from his wife.

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Appearing on Steve Harvey‘s talk show earlier this month, the Skinnygirl founder revealed where things currently stand with Shields — though she didn’t identify him by name.

“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. 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. So both partners have to say, ‘All right, I’m in it for this.’ ”

“And I think we might be at that point, believe it or not,” she added. “I haven’t said that to anyone yet.”

Frankel went on to tell PEOPLE Now that while she likes to keep their relationship private, “if there’s anything major that anyone should know, I’ll be the first to let them know.”