Jon Hamm and Anna Osceola: A Splash in Italy's Coastal Paradise

Jon Hamm and Anna Osceola's Sultry Italian Getaway: A May-December Romance That's Heating Up

It seems like Mad Men's Don Draper has finally found his true love, but this time it's not on Madison Avenue, but on the sun-kissed Amalfi Coast. Jon Hamm, 54, and his stunning wife Anna Osceola, 37, are celebrating their second wedding anniversary in style, and The Scholarly Note has got all the juicy details.

The Emmy-winning actor was spotted admiring his wife's "pert posterior" as they lounged on a beach in Minori, Italy. And who can blame him? Anna Osceola is a vision of loveliness in her underwire bandeau top and matching Brazilian bikini bottoms, showcasing her slim 5'11" figure. The flame-haired beauty seemed relieved to be escaping the sweltering humidity and heat of the summer sun by jumping off their cove-side cabana.

But what's really cooking between Jon and Anna? Sources close to the couple claim that they're eager to start a family, with Jon hinting at settling down in an interview last year. "Marriage has been great," he gushed. "And I hope it turns into kids." But will their age gap of 17 years be a challenge for the couple?

Jon's diving skills were put to the test as he plunged into the sea, sporting a pair of purple-patterned swim trunks. And it seems like he's still got it – after all, who can forget his iconic scene in Mad Men where he wore clingy khakis? The actor even named his rescue dog Splash during the height of the COVID-19 pandemic.

But what really caught our attention was Jon's sweet gesture towards Anna. After their swim, he wrapped one of the resort's pink-striped towels around his shoulders and shared a romantic cheers with his wife over iced tea. It's clear that their love is still going strong, especially after they met on the set of Mad Men back in 2013-2014.

Their romance began when Jon was still dating Jennifer Westfeldt, but he ended their 18-year relationship in 2015 due to reportedly treating her like a "manager or mother." But it seems like Jon has finally found his match with Anna. The two-time Golden Globe winner has even helped Anna secure several acting gigs, including a recurring role as Rebecca Naomi Jones' onscreen wife Maggie Haber in his show Your Friends & Neighbors.

But don't think that their love is without controversy. After all, Jon has had his fair share of scandals, including a stint in inpatient treatment for alcoholism back in 2015. However, it seems like he's turned over a new leaf and is now focusing on his relationship with Anna.

Speaking of which, their social media accounts are filled with loving posts about each other. And who can blame them? Their love story is the stuff of fairy tales – from meeting on set to becoming one another's rock in the face of adversity. So what's next for this power couple?

Well, for starters, Jon will be reprising his role as financier-turned-thief Andrew 'Coop' Cooper in the second season of Your Friends & Neighbors, which premieres next year on Apple TV+. And if you thought that was all – think again! The actor will also be voicing the greedy Mayor Jerry in Daniel Chong's sci-fi comedy Hoppers, set for release in US/UK theaters on March 6.

But what really gets our gears going is the fact that Jon and Anna are now co-owners of a new production company. And with their combined talents, they're sure to bring some seriously hot projects to the small screen. Stay tuned!

And there you have it – the scoop on Jon Hamm and Anna Osceola's sultry Italian getaway. With all the romance, drama, and excitement, we can't help but wonder what's next for this power couple. Will they start a family? Will they produce more shows together? One thing is certain – their love story will be one to watch in the coming months.

Related Stories:

• Jon Hamm and Anna Osceola's Love Story: From Set to Reality
• The May-December Romance That's Captivating Hollywood
• Jon Hamm's Journey from Mad Men to Marriage and Beyond