MAYFIELD VILLAGE, Oh – Progressive Insurance’s most dedicated employee, Flo, is falling in love – well, maybe.

In a new advertising campaign, set to launch Monday, May 23, consumers will get another chapter of Flo’s story — one that links her to one of the most loved actors in Hollywood — Jon Hamm.

During the three-commercial series, “Flo’s Love Interest,” we find the two were set up on a blind date when he was still a struggling actor. He liked her, but she only seemed interested in saving him money on his home and auto protection.

This unlikely pairing and love story arc is a first for Flo, played by comedian Stephanie Courtney, and Progressive’s line-up of campaigns and characters.

“Flo has been at the heart of Progressive’s marketing for nearly fifteen years. We’ve witnessed her undying love of insurance, watched as friendships have developed, and have even met her family, but one aspect of her life has remained a mystery—until now,” said Progressive’s Chief Marketing Officer Remi Kent. “In partnering with Jon Hamm, we fan the flames of brand love in a way that consumers can relate to, because who hasn’t experienced the awkwardness of unrequited love.”

The advertising campaign follows Flo navigating an unexpected encounter on the street with Hamm. While he, again, seems eager to capture her heart, Flo only has room for one love in her life: insurance. The commercial series is slated to run nationally throughout the summer on broadcast and digital channels, as well as Hulu.

Years after their unsuccessful blind date — and his subsequent rise to stardom – Hamm once again crosses paths with Flo, rekindling his interest in the apron-clad insurance maven. The three-part journey features Hamm pining for Flo’s attention, complete with romantic gestures and unexpected insurance emergencies.

Why Hamm?

“Like any episodic story, guest stars and are a great way to bring new life into familiar storylines,” said Lauren DeVito, an account executive with Allison + Partners, Progressive’s New York ad agency. “When choosing our guest stars, we look to identify those who have deep followings or are culturally relevant. That’s why we chose Jon, one of the most well-known actors in Hollywood. Additionally, his name is synonymous with the advertising world thanks to his iconic role on ‘Mad Men,’ so he was a no-brainer to work with.”

“Unanswered love is something we can all relate to, so I was thrilled to be able to play a role in this campaign,” said Hamm, in a release from Progressive. “I really enjoyed the dynamic between Flo and I and was excited to play myself in a campaign with a trusted brand and an iconic character.”

Will Hamm win her affections? Will Flo stay true to herself, offering insurance discounts whenever and however she can? We will just have to watch to find out.

Progressive is the third-largest auto insurer in the country and is one of the top 15 homeowners’ insurance carriers.