Rob McElhenney and Kaitlin Olson's Relationship Timeline: From Co-Stars to Soulmates

Actor Rob McElhenney and his wife Kaitlin Olson were co-stars long before they became love interests. It all started in 2002 when Rob developed a crush on Kaitlin but admitted he thought she was "out of [his] league." In a heartfelt 2020 Instagram post, Rob reflected on his first time seeing Kaitlin on Curb Your Enthusiasm.

He began, "I remember watching an episode of Curb Your Enthusiasm in 2002 — before I even moved to LA — and seeing this woman playing Larry’s sister-in-law. I thought she was so funny and so beautiful and so out of my league."

A few years later, they officially met on the set of It’s Always Sunny in Philadelphia in 2005. Shortly after, the two started dating. Their love story is one for the books, so let’s take a look at Rob and Kaitlin’s relationship timeline from the beginning to now.

After meeting at a casting call for It’s Always Sunny in Philadelphia in 2005, Kaitlin almost lost out on the role of Deandra "Sweet Dee" Reynolds after leaving out a line. Rob was flabbergasted and immediately pointed it out, per an interview she had with BuzzFeed, making her think she had blown her chance.

Fortunately, that wasn’t the case — she landed the role, and fate had even more in store. By 2006, sometime while filming Season 2, the two began dating. It seems destiny brought them together because, after that, they’ve been inseparable. However, the It's Always Sunny cast wouldn't find out about their dating until the show's third season.

By 2007, Rob and Kaitlin got engaged, and the following year, they tied the knot on Sept. 27, 2008. The couple wed at a vineyard in Malibu, and of course, Danny DeVito was among the guests in attendance.

Kaitlin and Rob revealed they were expecting their first child in May 2010, and by September, their son, Axel Lee, was born. "I went into labor at the Phillies/Dodgers game on Tuesday night," Kaitlin told People.

Giving themselves time to settle in as first-time parents, Rob and Kaitlin welcomed their second son, Leo Grey, on April 5, 2012. Kaitlin gave birth to Leo at their Los Angeles home, she revealed to People.

When it comes to her kids and family life, Kaitlin likes to keep things private. During her 2015 interview with BuzzFeed, she shared, "I just feel like my motherhood life is sort of private, because it's so special to me I don't want it attacked or to have that part be annoying to people."

After balancing parenthood and their busy careers, Rob has never missed a chance to gush over Kaitlin on social media. One of his most memorable birthday tributes came on Aug. 18, 2022, when he posted a throwback photo of a young Kaitlin rocking some serious ’80s hair. "I love this woman more than she loved her Aqua Net in 1988," he wrote. "Happy birthday you awkward a-- beautiful perfect specimen."

A big moment in Rob and Kaitlin’s professional lives came when Rob won an Emmy in 2023 for Outstanding Unstructured Reality Program for Welcome to Wrexham, a show he executive produces. He secured another win in 2024 in the same category, further cementing his success.

Kaitlin, meanwhile, was also up for an Emmy in 2024 but lost out to Jamie Lee Curtis. After the show, she joked that while she still doesn’t have an Emmy, at least now she can complain about it, though Rob no longer has the privilege of doing the same.

Rob and Kaitlin continue to operate as a united front, frequently celebrating each other on social media — whether it’s hyping up career milestones or just appreciating one another. While they keep their kids out of the spotlight, it’s clear they’re one big, happy (and incredibly talented) family.