Entertainment Movies Jon Hamm Says He's 'Very Much' in Love with Anna Osceola, and Marriage and Kids Are a 'Possibility' Jon Hamm and Anna Osceola made their red carpet debut earlier this year after nearly two years of dating By Alexandra Schonfeld Alexandra Schonfeld Alexandra Schonfeld is a features writer at PEOPLE. She has been working at PEOPLE since April 2022. Her work previously appeared in Newsweek. People Editorial Guidelines Published on September 20, 2022 09:56AM EDT Jon Hamm is thinking about the future. In an interview with Howard Stern for a recent episode of The Howard Stern Show, the Mad Men alum, 51, opened up about how he feels "very settled and comfortable" at this stage of his life and in his relationship. "I'm in a relationship right now and ... it's comfortable, it's a feeling of taking care of someone else and being taken care of," Hamm said. Hamm, who made his red carpet debut with girlfriend Anna Osceola at an Oscars party earlier this year, has been romantically linked to her since 2020, though they'd been spotted out together earlier. It is believed the two met in 2015, when Osceola appeared on the series finale of Mad Men as the receptionist at the spiritual retreat where Hamm's character was seen in the episode's last moments. Hamm said that it took him time — and therapy — to get to a place where he could begin to think about the future of their relationship. Jon Hamm and Anna Osceola. Chelsea Lauren/Shutterstock "It's also been a process of working on myself, my mental health, all the stuff with my therapist. And unpacking all of that trauma and realizing that when you lose someone that's so important to you, like a mother, so early, that that creates a wound that blocks a lot of that emotional accessibility," Hamm, who lost his mother at age 10, explained. "That blocks a lot of that availability and vulnerability." He continued, "It's only been in the last couple of years, me kind of sitting down and really thinking about all that stuff, that's made the relationship that I'm in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness ... It sounds hokey and whatever, but it's real and it's — for want of a better word — it's what I'm working for." Jon Hamm Will Play a 'Corporate Titan' in Season 3 of The Morning Show Jon Hamm and Anna Osceola. Timothy Norris/FilmMagic Stern, 68, then asserted that it sounds like the actor is "in love." "I very much so am," Hamm agreed. Jon Hamm and Anna Osceola Enjoy Fun Day of Swimming and Snorkeling While Vacationing in Italy The couple's red carpet appearance in March was their first "official" outing after years of dating, as they have largely kept their relationship private. Prior to his relationship with Osceola, Hamm was in a long-term relationship with actress Jennifer Westfeldt. In 2015, PEOPLE broke the news of the pair's split after 18 years together. "We will continue to be supportive of each other in every way possible moving forward," they said in a joint statement.