In 2015, Jon Hamm’s life fell apart. An old criminal investigation and prosecution from his college days came to light, and it turns out he was the ringleader of violent fraternity hazing assaults when he was in Texas. That all came to light in 2015. Then Mad Men ended, then Hamm went into rehab, and then he and Jennifer Westfeldt were done after eighteen years together, longer than most marriages and what was (in essence) a common-law marriage. In recent years, Hamm has been with Anna Osceola, who is 34. Hamm is 51. Now they’re engaged:
Jon Hamm and Anna Osceola are engaged! The Confess, Fletch costars are set to wed after two years of dating, PEOPLE confirms. The pair first reportedly met on the set of the AMC series Mad Men in 2015, before being spotted together on several occasions and romantically linked in 2020. Hamm’s rep has not commented.
Osceola, 34, appeared in the series’ final episode, where she had a small role playing the receptionist at Esalen, a spiritual California retreat that Hamm’s character (Don Draper) attended. At the time, Hamm, 51, was in a long-term relationship with Jennifer Westfeldt. The couple split months later after 18 years together.
Hamm and Osceola, who both keep off social media, were photographed together once in 2017; romance rumors took off in 2020 when they were seen out multiple times. Since then, they’ve been spotted stepping out for meals, playing tennis and enjoying a day at the beach. They also took a vacation to Italy together in September 2021.
How are we calling this “two years of dating” when they’ve likely been together since 2017? The math isn’t mathing. As for this engagement… one of the biggest mysteries (for me) of Hamm’s relationship with Westfeldt was why they never married and which one of them was reticent. We heard different things over the years, that Hamm was up for it and she wasn’t, or vice versa. I don’t know. After nearly two decades in a long-time partnership, it must be hard to watch your ex propose to his next serious girlfriend. Sigh… in any case, congrats to Hamm and Anna Osceola.
Photos courtesy of Avalon Red, Backgrid.
Jon Hamm and Anna Osceola attends the 2022 Vanity Fair Oscar Party Hosted By Radhika Jones celebrating the 94th annual Academy Awards at the Wallis Annenberg Center for the Performing Arts on March 27, 2022 in Beverly Hills, California,Image: 673516037, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm and Anna Osceola, Credit line: – / JPI Studios / Avalon 
SAN DIEGO, CA – MAY 04: (L-R) Jon Hamm and Anna Osceola attend the ‘Top Gun: Maverick’ World Premiere onboard the USS Midway Museum on May 04, 2022 in San Diego, California.,Image: 689032375, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm, Anna Osceola, Credit line: Jeffrey Mayer / Avalon 
Jon Hamm arrives for the Top Gun Maverick Premiere, London, UK,Image: 692788394, License: Rights-managed, Restrictions: , Model Release: no, Credit line: James Shaw / Avalon
HOLLYWOOD, LOS ANGELES, CALIFORNIA, USA – JULY 20: American actor Jon Hamm and girlfriend/American actress Anna Osceola arrive at the 2022 ESPY Awards held at the Dolby Theatre on July 20, 2022 in Hollywood, Los Angeles, California, United States.,Image: 708815152, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm, Anna Osceola, Credit line: Xavier Collin / Image Press Agency / Avalon 
HOLLYWOOD, LOS ANGELES, CALIFORNIA, USA – JULY 20: American actor Jon Hamm and girlfriend/American actress Anna Osceola arrive at the 2022 ESPY Awards held at the Dolby Theatre on July 20, 2022 in Hollywood, Los Angeles, California, United States.,Image: 708815165, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm, Anna Osceola, Credit line: Xavier Collin / Image Press Agency / Avalon 
Los Angeles, CA – Jon Hamm and girlfriend Anna Osceola attend Derek Jeter’s benefit at The Highlight Room. Pictured: Jon Hamm, Anna Osceola BACKGRID USA 19 JULY 2022 USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*ncG1vNJzZmivp6x7pLHLnpmirJOdxm%2BvzqZmcWhmaH11e8mopZigkaK6oIGQmKCsl5WjtKKzxJ2WraePlruvrb6oqpydn6GuoH%2BTmJifrJWnrLXDzpiwnpmiqKywsr6dmK2hnpx8