’90 Day Fiance’: What REALLY Does Dempsey Wilkinson Do for a Living? đ€
90 Day Fiance star Dempsey Wilkinson had some of the most problematic stories in the latest season of TOW. Sheâs currently sharing her struggles with Statler Riley. The two decided to live in a van, but they now face financial problems. This led some Redditors to be curious about Dempseyâs career, especially with all the travel posts she makes online. Keep reading to see the discussion.
90 Day Fiance: Dempsey Wilkinson & Statler Rileyâs Van Life
Statler and Dempseyâs current story revolves around their van life. The 90 Day Fiance stars decided to live off the grid. It was Dempseyâs dream to live in a van. However, Statler was not happy about it, but she had no choice but to support her girlfriendâs needs.

Statler decided to dig into her own pockets for $20,000 for the van. But things suddenly went sideways when the couple started struggling financially. Statler ended up being short on her paycheck to cover the bills for the van. Since then, their road trips have turned into an emotional roller coaster.
The Truth Behind Dempseyâs Career
Some Redditors discussed Dempsey Wilkinsonâs career, which remained a mystery for quite some time. According to the poster, theyâre curious about how the 90 Day Fiance star is able to fund all of her expensive travels. This made the OP curious if she was comfortable being a drifter.
Several commenters pointed out that Dempsey doesnât really have a job and mostly relies on Statler Riley. One of the only known jobs she has taken was working for a friendâs staycation business called Kip & Nook in Darlington.

- âShe doesnât do anything. I think she would pick up random jobs when needed, but this time she banked on Statler just working and her living the life. I donât blame Statler for being pissed. Dempsey doesnât live in the real world.â
- âSheâs a âtravelerâ, which is a few different sorts of cultures in Europe. They tend to work odd jobs, which is what we seen on her first season â sheâd taken up residence in exchange for pay and a small house, which Statler also complained about, lol.â
- âGrift. She said she would get jobs when she needed as a barista or something.â
- âI thought she mentioned in passing her family were carnies? But I assumed she was a traveler as well.â
90 Day Fiance: Dempsey Wilkinsonâs New Girlfriend
Things have also fallen apart between Statler Riley and Dempsey Wilkinson behind the cameras. Dempsey now has a new girlfriend named Anayeli Trujillo. Sweet photos of them have also surfaced online.
On the other hand, Statler suddenly went off on social media following the reveal of Dempseyâs girlfriend. The 90 Day Fiance star even called out Anayeli, asking her to tell Dempsey to give back her $20,000 and some of her belongings, including sentimental teddy bears.