NEW YORK (CBSNewYork) — “Real Housewives of New York City” star Bethenny Frankel’s on-again, off-again boyfriend was found dead in his Trump Tower pad Friday of a suspected overdose.

Dennis Shields had asked his assistant to administer Narcan around 9 a.m., believing he was overdosing on prescription pills, sources said.

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But the 51-year-old lost consciousness before the medication used to reverse an opioid overdose started working. He was pronounced dead a short time later.

Frankel and Shields began dating in 2016.

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In May, the reality TV star told Steve Harvey that their relationship was complicated, according to People.

“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.”

The one-time boyfriend of “Real Housewives of New York City” star and entrepreneur Bethenny Frankel was found dead of an apparent overdosed at Trump Tower Friday morning, law enforcement sources says.

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Dennis Shields, 51, was once linked to Frankel. It is unclear the status of their relationship.