90 Day: The Last Resort recently unveiled an intriguing new couple during its Tell All segment. The revelation came when Josh Weinstein disclosed that he was dating Elizabeth Potthast‘s sister, Jaylyn Davis, who is also known as Jenn Potthast. The pivotal question remains: are they still together following this public announcement? Josh, 43, is recognized by fans of 90 Day Fiancé as Natalie Mordovtseva’s former romantic partner, having appeared in 90 Day: The Single Life where they navigated a tumultuous, on-and-off relationship.
Their time on the spin-off was marked by Josh’s reluctance to categorize Natalie as his girlfriend, despite her persistent efforts to maintain their connection. While Natalie believed she could win Josh back, he swiftly moved on after their breakup, while she intermittently claimed to be dating someone else. However, Natalie’s cold demeanor towards Jenn paints a different narrative.
A Three-Year Relationship with Natalie
Josh’s Perspective on Natalie
Josh made his mark in the 90 Day Fiancé universe during season 2 of The Single Life. Initially, Natalie appeared indifferent towards him, particularly due to his past relationships and his explicit disinterest in having more children. This difference in future aspirations led to tension, especially as Natalie had long anticipated motherhood. However, Josh’s stable career likely drew her to him, prompting her relocation from St. Petersburg to California.
“I’m so attracted to him. I just can’t stay away.”
Despite her affections, Natalie kept her ex-husband Mike in the picture, recognizing Josh was not ready for marriage. His mixed signals caused confusion, leaving Natalie jealous of the attractive women around Josh at his work. The strain escalated, and eventually, she broke away when realizing Josh was unlikely to fulfill her dreams of family. Their paths crossed again during the filming of The Last Resort, but their relationship seemed plagued with dissatisfaction and insecurities.
Jenn’s Backstory: Marriage to DJ Orlando Davis
Unpacking Jenn’s Previous Marriage
Jenn Potthast previously made her presence known in seasons 5 to 7 of 90 Day Fiancé: Happily Ever After?. Before her current relationship with Josh, she was married to Orlando Davis, a well-known Florida DJ and host of “Orlando and the Freakshow” on WiLD 94.1. Their marriage ended in divorce on September 1, 2011, and since then, they have co-parented their two daughters, Kaelyn and Brielle.
Dating Speculations in 2023
The Onset of Romance
Natalie’s ex Josh and Libby’s sister Jenn out together. Do you think they are trolling us or really together? They seem attention seeking to me… by u/SignificantCamel8516 in 90DayFiance
Dating rumors regarding Josh and Jenn began circulating in April 2023 when Josh posted a flirty Instagram video of them dining with friends. Observed by a Reddit user, the video depicted Josh casually toasting with Jenn, who playfully posed beside him, igniting speculation about their relationship status.
Family Ties Between Josh and Jenn
Jenn’s Mother and Josh’s Connection
Jenn’s mother, Pamela Putnam, is a talent agent and operates Stellar Talent and Image, a boutique agency that represents various artists, diverging from the Potthast family’s house-flipping ventures. Jenn’s sister, Elizabeth, has also pursued acting, making them acquainted with the entertainment industry, which likely facilitated Josh’s long-standing familiarity with Jenn and her family.
Formal Introduction at the Tell All
Revelation of Josh’s Partner
Speculation about Josh’s romantic interests ramped up during an interview on “The Sarah Fraser Show,” leading fans to question if he and Jenn were involved. This intrigue culminated in the Last Resort‘s Tell All, where Josh confirmed Jenn’s identity as his girlfriend, expressing his affections for her. He indicated they shared a familiar connection, having known one another for seven years and enjoying various outings together.
Current Status of Josh and Jenn’s Relationship
Assessing Their Relationship Dynamics
During a conversation with Shaun Robinson, Josh mentioned plans to meet Jenn in the upcoming month or so, suggesting a possible trip to Las Vegas. However, Jenn clarified that their relationship is still “very new”and not serious as they are currently “not exclusive.”Given that the Tell All filming occurred in January 2025, it’s plausible that their trip has already taken place, but they have not publicly acknowledged their relationship on social media.
90 Day Fiancé airs Sundays at 8 p.m. EDT on TLC.
Source: InTouch, u/SignificantCamel8516/Reddit