Jon Hamm Steps Out with Anna Osceola in Santa Monica, Plus Rita Ora, Ashlee Simpson & Evan Ross and More
![Jon Hamm goes casual as he heads out to play tennis with longtime rumored girlfriend Anna Osceola | Daily Mail Online Jon Hamm goes casual as he heads out to play tennis with longtime rumored girlfriend Anna Osceola | Daily Mail Online](https://i.dailymail.co.uk/1s/2020/05/23/04/28727720-0-image-a-19_1590203487676.jpg)
Jon Hamm goes casual as he heads out to play tennis with longtime rumored girlfriend Anna Osceola | Daily Mail Online
![Jon Hamm's secret long-term girlfriend revealed, plus more celeb love life news for late June 2020 | Gallery | Wonderwall.com Jon Hamm's secret long-term girlfriend revealed, plus more celeb love life news for late June 2020 | Gallery | Wonderwall.com](https://www.wonderwall.com/wp-content/uploads/sites/2/2020/06/bgus_1944994_002.jpg?h=800)
Jon Hamm's secret long-term girlfriend revealed, plus more celeb love life news for late June 2020 | Gallery | Wonderwall.com
![Jon Hamm & Girlfriend Anna Osceola Spotted on Friday Night Dinner Date! | Anna Osceola, Jon Hamm | Just Jared Jon Hamm & Girlfriend Anna Osceola Spotted on Friday Night Dinner Date! | Anna Osceola, Jon Hamm | Just Jared](https://cdn.justjared.com/wp-content/uploads/headlines/2022/04/jon-hamm-date-night-with-girlfriend.jpg)
Jon Hamm & Girlfriend Anna Osceola Spotted on Friday Night Dinner Date! | Anna Osceola, Jon Hamm | Just Jared
![Jon Hamm, 51, and girlfriend Anna Osceola, 34, head out on errand run in The Hamptons | Daily Mail Online Jon Hamm, 51, and girlfriend Anna Osceola, 34, head out on errand run in The Hamptons | Daily Mail Online](https://i.dailymail.co.uk/1s/2022/07/28/23/60816091-11059827-image-m-5_1659046006169.jpg)
Jon Hamm, 51, and girlfriend Anna Osceola, 34, head out on errand run in The Hamptons | Daily Mail Online
![Jon Hamm & Girlfriend Anna Osceola Spotted on Friday Night Dinner Date!: Photo 4742026 | Anna Osceola, Jon Hamm Pictures | Just Jared Jon Hamm & Girlfriend Anna Osceola Spotted on Friday Night Dinner Date!: Photo 4742026 | Anna Osceola, Jon Hamm Pictures | Just Jared](https://cdn.justjared.com/wp-content/uploads/2022/04/hamm-date/jon-hamm-date-night-with-girlfriend-05.jpg)