Jon Hamm & Fiancee Anna Osceola Grab a Drink While Running Errands

Jon Hamm and his fiancee Anna Osceola stop for drinks while running errands in Los Feliz, Calif.

The 52-year-old Emmy-winning actor kept it casual in a pair of jeans, button up shirt and tan jacket. He wore a baseball cap. Anna wore a striped shirt with jeans, too.

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If you were unaware, reports started circulating that the couple was engaged earlier this year. Jon and Anna have been linked since 2015 when they met on the set of Mad Men.

The couple made their red carpet debut as an engaged couple at the 2023 Vanity Fair Oscar Party in March.

Last year, Jon opened up about his relationship with Anna, revealing his thoughts on tying the knot.

“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,” he explained.

Scroll through all the new photos of Jon Hamm and Anna Osceola in the gallery…