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The Daily Dish The Valley

Jesse Lally Details His Whirlwind Romance with Anna Nicole Smith: "Like Two Little Kids"

The Valley cast member said he became romantically involved with Anna after they worked together a 2002 campaign shoot. 

By Joshua Espinoza
What Changes Have Jesse Lally and Michelle Sainei Lally Made for Their Relationship?

Jesse Lally’s connection to Anna Nicole Smith was much juicier than he initially led on.

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During his May 21 appearance on Watch What Happens Live with Andy CohenThe Valley dad confirmed he and Anna had worked together on a 2002 campaign for the now-defunct diet pill TrimSpa. He told the host that he and the late model became “friends” on set and remained so “for, like, a year and a half.”

However, Jesse told a much different story a few weeks later, revealing he and Anna were romantically involved for quite some time. He shared the “juicy nugget” in the June 4 episode of the Popping Off podcast hosted by The Real Housewives of Beverly Hills alum Teddi Mellencamp Arroyave and The Real Housewives of Orange County’s Emily Simpson.

Jesse Lally claims he "hooked up" with Anna Nicole Smith decades ago

Just minutes into the sitdown, Teddi bluntly asked Jesse if he ever “hooked up” with Anna, to which he replied, “For a year or two. Yeah.”

The hosts were understandably shocked and pushed for more details. Jesse said the romance was long-distance, as they would only see each other whenever Anna went to New York City (where he was based at the time) or when he would travel to Los Angeles (where Anna primarily resided). He then detailed their first night together, which occurred immediately after the aforementioned TrimSpa shoot. 

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How did Jesse Lally meet Anna Nicole Smith?

Split of Jesse Lally at WWHL and Anna Nicole Smith wearing a black dress at an event.

“The story was interesting: We were shooting in Miami [in] 2002 and the first time I met her — the first layout was an old James Dean-Marilyn Monroe photo, where Marilyn’s naked on a mattress and James Dean has no jeans and no shirt on in front of her. And 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 said a portion of the campaign was shot on the beach and involved Anna getting in the water. As the day came to a close, Anna told Jesse she hoped she didn’t get sick “from walking wet in the cold.” He then told the former Playmate he had “a ton of supplements and vitamins” in his hotel room that could help prevent mild illnesses.

“Is that your line? Your go-to?” Teddi sarcastically asked.

“Yeah, she called me,” Jesse continued. “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 and before the two massage therapists showed up, she was like, ‘Let’s kind of [mess] with them a little bit.’ So we were going back and forth, making jokes, talking like you know, trying to see if something would come out [in the media]. And this is way before social media, and it was just fun. We just had that relationship. We were just kind of like two little kids messing with each other.”

Jesse Lally confirms he's in a relationship following split from Michelle Lally

Jesse Lally and Lacy Nicole on a red carpet for Sparkle's Drag Spectacular benefiting the Leukemia and Lymphoma Society

According to Jesse’s timeline, his romance with Anna ended several years before she tragically died of an accidental overdose. The model/reality TV star was survived by her now 17-year-old daughter, Dannielynn Birkhead, whom she shared with her on-again, off-again boyfriend Larry Birkhead.

In 2018, Jesse tied the knot with fellow realtor Michelle Saniei Lally. The two welcomed their first child together — a daughter named Isabella — in 2020 and announced their separation in March 2024. Since then, Jesse and Michelle have started new relationships: the former is dating philanthropist Lacy Nicole while the latter is involved with financial advisor Aaron Nosler.

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