Anna Osceola and Jon Hamm were spotted swimming and kissing on the beaches of Italy, and fans are gushing at how cute they looked together!

In fact, Anna and Jon were spotted together quite often during the pandemic. Here’s everything you need to know about Anna Osceola.

Anna Osceola Worked With Jon Hamm on Mad Men

The pair first met on the set of Mad Men. Jon Hamm was playing the dashing ad executive Don Draper and Anna was playing Clementine, the lovely receptionist at a wellness retreat. She only appeared during the series finale, but it must have been enough to capture Jon’s heart.

While the pair didn’t get together right away, they have kept in touch over the years. In 2017, they were seen getting coffee together, and in 2018, fans spotted the couple playing tennis. During that time, Jon was also spotted with Lindsay Shookus and fans thought they were dating when they went to a Broadway show together.

It is unclear when Anna Osceola and Jon first started dating with their long history, but they have definitely gotten close since the pandemic. The couple may have been quarantining together because they were spotted playing tennis in Los Feliz, Calif. They were also seen picking up takeout and groceries.

Anna Osceola Has a Long List of Acting Credits

Mask up! Jon and Anna are experts at choosing matching outfits. Photo credit: BACKGRID

Mad Men wasn’t Anna’s first acting role. Originally from Cambridge, Mass., the 33-year-old made her acting debut when she starred as Charlie in the TV movie, Not Another High School Show. Since her first acting gig, Anna appeared on shows such as Greek, where she played Robin Wylie, Rizzoli and Isles, Law & Order Special Victims Unit, and Bull.

Most recently, the actress played the role of Noelle Terlesky in the TV mini-series, Law & Order True Crime. The series focused on the Menendez Murders.

Anna Osceola Has a Killer Bikini Body

How gorgeous are Jon and Anna! Photo credit: BACKGRID

During their recent beach trip in Italy, Anna showed off her amazing body in red bikini bottoms and a green bandeau top. She perfectly matched her boyfriend who was wearing red swim shorts. Jon and Anna were seen cuddling and kissing in the water and fans found their PDA to be completely adorable.

The pair was also seen relaxing on the beach. At other times Jon could seen diving off a small cliff into the ocean. His form was incredible and his dad bod was seriously hot!

Anna Osceola Isn’t The First Actress Jon Has Dated

Jon Hamm famously dated actress Jennifer Westfeldt for 18 years. Fans were shocked when the couple broke up in 2015 because they always thought the pair would one day get married. When they split, the couple released this joint statement letting fans know that they would still remain friends:

“With great sadness, we have decided to separate, after 18 years of love and shared history,” the former couple said in a statement to People magazine. “We will continue to be supportive of each other in every way possible moving forward.”