How fun is single life for a perennial on those sexiest-man-alive lists? “It’s fine,” he says before adding quietly, “It’s hard.It’s hard to be single after being together for a long time. It sucks.” RELATED: How Nicole Kidman Hit the Peak of Her Career—Again Two years ago Hamm did a stint in rehab for alcohol addiction, and although he prefers to keep the specifics to himself, he’s outspoken about the benefits of therapy.I see it, and I f—ing weep.” VIDEO: Jon Hamm is an Excellent Driver Hamm and I are in the midst of a long, candid chat at a restaurant in the Hollywood Hills.I’ve already assured him I won’t spend this entire story comparing and contrasting him with his stoic Mad Men alter ego, Don Draper, which is the main angle of pretty much every Jon Hamm profile ever written.Regardless of their relationship status, it's still a nice gesture to thank someone who has supported you throughout your entire Mad Men journey and the past 18 years of your life.But maybe it's also a little hint at something — a spark that maybe their relationship isn't over for good.“We all want to be involved in something that takes hold of the culture and makes people sit up and say, ‘Hey, that’s interesting,’ ” he says. I never wanted to be a Tom Cruise type of megastar.” For Hamm, life after Draper has come with some inevitable complications, including a few personal ones.In 2015 he split with his partner of 18 years, writer-director Jennifer Westfeldt.
Jennifer is an American actress and filmmaker, who is perhaps best known for writing and starring in the indie hits, Kissing Jessica Stein (2001) and Friends with Kids (2011). “Edgar is an original artist, and I just love his work,” says Hamm.“Whether his films are commercially successful, I don’t give a s— about.” Hamm suddenly excuses himself to say hello to “a friend”—that would be Sean Penn—at a nearby table and returns about 45 seconds later, apologizing for the interruption.With his Blues cap, bro-ish saunter, and generic outfit (a blue American Apparel shirt, black jeans), Hamm goes mostly unrecognized in the restaurant.For much of his life, he says, he’s been “oblivious” to fashion, but that changed when he began suiting up for his role in Mad Men. RELATED: Jon Hamm’s Changing Looks Does Hamm pay much attention to what women wear? “I’m a heterosexual male, and I love a lady with style.” Aside from a few “ridiculous” fashion trends that leave him bewildered, Hamm likes it when a woman is confident enough to express her individuality through her clothes.A few months later, in November 2015, the two were spotted "arm-in-arm" at a tribute to their late friend, director Mike Nichols.The New York Daily News reported that Hamm and Westfeldt arrived at the ceremony together and the actress had her arm linked through her ex's, a gesture that prompted the newspaper to blare the headline "Exes Jon Hamm, Jennifer Westfeldt Get Cozy." To be fair, any former couple at a memorial for their friend would probably reach out in a gesture of support — but still, this same move could also be interpreted as a reconciliation.“I think anything that serves to accentuate whatever your thing is and makes you feel good shows in the way you carry yourself,” he says.On most fronts these days, Hamm seems determined to tune out trivialities in favor of all things substantive and real.Forget Gwen Stefani and Gavin Rossdale, and Blake Shelton and Miranda Lambert — one of the saddest celebrity splits of last year was Jon Hamm and Jennifer Westfeldt, who broke up in September 2015 after 18 years together.Their breakup seemed almost inconceivable to fans of the couple, especially after Hamm credited his longtime girlfriend for her extensive support after he completed rehab for alcohol addiction.