Jon Hamm and wife Anna Osceola stepped out for a date night at the 2026 Emmy Awards one month after news broke that they’re expecting their first baby.
Hamm, 55, sported a black suit as he walked the red carpet outside the Peacock Theater in Los Angeles on Monday, September 14. Osceola, 38, wore a drapey black-and-white chevron-patterned dress with a high neck for the occasion and cradled her baby bump as she posed alongside her husband ahead of the awards show.
Multiple outlets reported in August that Osceola is pregnant with her and Hamm’s first child. In photos obtained by the Daily Mail at the time, the Your Friends & Neighbors actress showed off her baby bump in a bikini during a getaway with the Mad Men star to the Hamptons.
Hamm and Osceola met while filming Mad Men’s series finale in 2015, when she played receptionist Clementine. (Hamm starred in the AMC drama as Don Draper from 2007 to 2015.)
The pair were first romantically linked in 2017, before Us confirmed their relationship in June 2020. The couple got engaged in February 2023 and wed that summer.
Amid the baby news, a source exclusively told Us that Hamm and Osceola are thrilled to be starting a family together.
“Jon has always wanted to be a dad with Anna,” the insider shared. “Having a family was something that was really important to both of them from the beginning. They’ve talked about this chapter for a long time and were always on the same page about wanting children, so for it to actually be happening now feels incredibly special.”
The source added that Hamm is “over the moon” at the prospect of fatherhood, and has been “so attentive and excited about every little milestone” during Osceola’s pregnancy.
“Anna is pretty far along now and feeling really good,” the source added. “She took it easy at first and tried to stay under the radar. They have been trying to relax a bit but are enjoying making plans for the baby.”
The insider concluded, “They’re both soaking it all in and are just so excited to become parents. Their relationship has only gotten stronger, and they feel really lucky to be going through this together.”
Hamm previously shared his hopes of becoming a dad in June 2024.
“I hope it turns into kids,” he told The Hollywood Reporter at the time. “It’s not lost on me that I’m 53. I will be the old dad, but so it goes. It could be a good thing. We’ll see.”
