Jesse Lally’s failed marriage to estranged wife Michelle Lally was his storyline during The Valley season 1, and now fans are stunned over his former fling with late Hollywood star Anna Nicole Smith.

The Bravo newcomer was featured in a few advertisements for the defunct weight loss drug Trimspa with Anna, who was the face of the brand at the time. Housewives Tamra Judge and Teddi Mellencamp ​Arroyave brought up Jesse’s past gig during the Wednesday, June 5, episode of their “Two Ts in a Pod” podcast, asking if Anna had a sexual relationship with Jesse.

“For a year or two,” Jesse, 43, responded. “I would come to L.A. and she’d be in New York every once in a while.”

“We were shooting in Miami [in] 2002. And the first time I met her, the first layout was an old James Dean and Marilyn Monroe photo where Marilyn’s naked on a mattress and James Dean has no jeans and no shirt on in front of her,” the real estate agent continued. “I literally walked over with no shirt on, sat down and she’s like, ‘Hi, I’m Anna Nicole.’ And I’m like, ‘Nice to meet you.’”

Jesse continued to reflect on the photo shoot where he pulled the Playmate into the ocean and pushed her underwater with him. Although the crew was allegedly “pissed” because her glam was ruined, the pictures – shot by photographer ​​Antoine Verglas – were the ones chosen for the campaign.

“I was literally in my room that night. She called me. I was having a bottle of wine in the room, and I was like, ‘Yeah, I can come up to the room.’ And it was funny. We did a couple’s massage,” Jesse continued. “We were just kind of like two little kids messing with each other.”

The Valley’s Jesse Lally Recalls Fling With Anna Nicole Smith
Jesse Lally/ Instagram

Tamra, 56, and Teddy’s spicy question was a follow-up inquiry from Jesse’s May appearance on Watch What Happens Live, when he first opened up about previously working with Anna. Back in 2013, Jesse shared a throwback photo with the late actress.

Anna became the spokesperson for TrimSpa in 2003. While being the face of the brand, the To the Limit actress featured in print and video advertisements. TrimSpa heavily declined after Anna’s death in 2007 at 39 years old after an accidental drug overdose. Anna was found unresponsive in her hotel room at the Hard Rock Hotel & Casino in Florida during a trip with partner Howard K. Stern. After Anna’s private nurse found her in the room, she was rushed to Memorial Regional Hospital, where she was pronounced dead.