![Jon Hamm, 51, and girlfriend Anna Osceola, 34, take their dog on a walk as they spend time together | Daily Mail Online Jon Hamm, 51, and girlfriend Anna Osceola, 34, take their dog on a walk as they spend time together | Daily Mail Online](https://i.dailymail.co.uk/1s/2022/08/03/02/61006811-0-image-a-107_1659491869072.jpg)
Jon Hamm, 51, and girlfriend Anna Osceola, 34, take their dog on a walk as they spend time together | Daily Mail Online
![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 & 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)
Jon Hamm & Girlfriend Anna Osceola Spotted on Friday Night Dinner Date!: Photo 4742026 | Anna Osceola, Jon Hamm Pictures | Just Jared
![All About Jon Hamm's Girlfriend Anna Osceola - Parade: Entertainment, Recipes, Health, Life, Holidays All About Jon Hamm's Girlfriend Anna Osceola - Parade: Entertainment, Recipes, Health, Life, Holidays](https://parade.com/.image/ar_1:1%2Cc_fill%2Ccs_srgb%2Cfl_progressive%2Cq_auto:good%2Cw_1200/MTg5Njg4NjI1OTU1MzQ5NzAx/jon-hamm-girlfriend-anna-osceola-ftr.jpg)
All About Jon Hamm's Girlfriend Anna Osceola - Parade: Entertainment, Recipes, Health, Life, Holidays
![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/hamm-date.jpg)
Jon Hamm & Girlfriend Anna Osceola Spotted on Friday Night Dinner Date! | Anna Osceola, Jon Hamm | Just Jared
![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)