Kaitlin Olson and Rob McElhenney's Relationship Timeline

From co-stars to Cupid's arrows.

Kaitlin Olson and Rob McElhenney

Mark Davis/Getty Images

What do you get when you put two comedians on a show together for 16 years? If you happen to be talking about Kaitlin Olson and Rob McElhenney, the answer is a loving relationship that spans more than a decade, two beautiful baby boys, and the longest-running live-action comedy series in history.

The pair, who fell in love on the set of It’s Always Sunny in Philadelphia, began dating in 2006 and got married two years later. “Literally, the stupidest thing you can do in the entertainment industry is start dating your co-star on a television series that’s expected to continue,” McElhenney told Buzzfeed in 2015. “Potentially, we could’ve ruined the dynamic of the TV series, but we jumped in anyway. I guess because I started to fall in love with her.”

Olson, for her part, told Metro in 2013 that sharing the small screen with her hubby for so long was “awesome,” adding, “He’s my favorite person.”

Keep reading to find out more about the couple through the years, from their unlikely beginnings to their adorable talk show appearance ahead of the 2022 Emmy Awards.

  • McElhenny and Olson didn’t hit it off upon first meeting.
  • The couple kept their relationship secret for an entire season of their shared show, It’s Always Sunny in Philadelphia.
  • McElhenney proposed to his costar at Danny DeVito’s beach house in Malibu.
  • They share two children, Axel and Leo, who were born in 2010 and 2012, respectively.

2002: A Date With Destiny

McElhenney revealed that his wife was on his radar years before they ever meet with a sweet throwback he posted to Instagram in March 2020. “I remember watching an episode of Curb Your Enthusiasm in 2002—before I even moved to L.A.—and seeing this woman playing Larry’s sister-in-law,” he wrote. “I thought she was so funny and so beautiful and so out of my league. Well, it’s eighteen years later and tonight I get to hold her hand, watch her on another episode of Curb and be reminded of all of those things again. What a lucky person I am.”

2004: A Not-So Meet Cute

Despite McElhenney's admirations from afar, it wasn’t exactly love at first sight for the pair, who both gave less than stellar opinions of each other after the Hacks star auditioned for the part of Dee Reynolds in McElhenney’s new show, It’s Always Sunny in Philadelphia. “My manager actually asked [after my audition], ‘Were any of them cute?’ And I was like, ‘Nah. Not really,'” Olson told EW in 2009 of her future husband before quickly adding, “But I do take it all back now.”

McElhenney, for his part, didn't think the actress gave her best performance. “She was flustered in the audition. She wasn’t that great the first time,” he told the magazine.

The actress elaborated on his critiques to Buzzfeed in 2015, saying, ““I left the room and Rob was like, ‘How did she leave out the funniest line that was in there?’ and he didn't want to cast me.” She added: “Rob, who I've now married, had to be talked into hiring me.”

2005: A Change of Heart

In a June 2018 episode of Dax Shepard's podcast, “Armchair Expert,” Olson told the show's host that she begin to develop feelings for her boss roughly halfway through the first season. "He was just so easily in charge," she recalled. "He really just has a vision and he's just a wonderful boss and he's a collaborator. But at the end of the day, he's very comfortable taking in information and then just making a decision."

2005: Making a Move

Olson also admitted to Shepard that it was she who made the first move on her now-husband. “I remember going to a game night at Charlie [Day] and Elizabeth [Ellis]’s and he was there, and I’d been drinking, ‘cause that's how I handled being nervous around him,” she recalled. “I would just move in to sit at the game and back up in between his legs, and like, move myself into his lap.”

McElhenney didn’t exactly return her advances, however—at least not initially. “He was just like, 'What—what are you doing?'” she said. “That's the other thing about Rob. He's unbelievably direct. Like, honest to a fault.”

August 4, 2005: Grand Debut

The first episode of the pair’s long-running series, It’s Always Sunny in Philadelphia, aired on FX on August 4, 2005.

The cast of "It's Always Sunny in Philadelphia"

Amanda Edwards/Getty Images

2006: Sneaking Around

By season 2 of the hit series, Olson and McElhenney were officially an item. “It was a very interesting dynamic,” Olson remembered to Dax Shepard on his “Armchair Expert” podcast. “Like, once I fell in love with him, I realized that I was deeply in love with him in a way that I hadn’t been in love with anyone before.”

While the show writer “really just wanted to be casual,” Olson was confident McElhenney would come around. “I was like, ‘This person is completely in love with me—and he has no idea.’ It was no problem for me,” she said. “It wasn’t even a game. It was just like, ‘Oh, you don't know, you have no idea that you are completely in love with me. That’s so cute!’”

After all, her new beau was giving off some not-so-subtle hints. “You want to have it casual and just date. Yet, you’re calling me every Friday night, and you’re spending the night, you’re staying through Saturday, and then, ‘Eh, just stay Saturday night,’ and then you see me at work on Monday morning,” she reasoned.

Still, the pair was careful not to get caught. "We were very sneaky at first because we thought, ‘This is a really bad idea.’ But then I fell in love with him," Olson told InStyle.

2006: Ground Rules

Once McElhenney did realize his feelings for his leading lady, he had a few boundaries to set forth, according to Dax Shepard, who discussed a conversation the producer had with Olson about their relationship on his podcast, “Armchair Expert,” in 2018. “[He said] ‘Look, I’m not a jealous person, I’m not gonna micromanage you. If you cheat on me, that’s the last time you’ll talk to me.” Olson said of her partner’s take-charge attitude,“It was very attractive!”

His other stipulation? Valentine’s Day. “My husband made it clear when we first started dating that there would be no Valentine’s Day in our relationship,” Olson told Jimmy Kimmel in a 2017 interview. “He laid down the law [and said] ‘For the record, we can tell each other we love each other year round but I won’t be doing Valentine’s Day.”

2006: A Defining Moment

Shortly into their courtship, McElhenney said an incident occurred that ultimately took the couple’s relationship to the next level. After a night of drinking, he wet the bed. “We had just started dating, not that long beforehand,” he recounted on “The Always Sunny Podcast.” “Enough to enough to where I was still like, ‘Oh, I want to impress this young woman.’” Instead, the show writer said he had an accident. “The next morning, she was like, 'Man you sweat like crazy last night. The sheets are soaking wet.'”

When she realized they were actually soaked in urine, however, Olson didn’t get mad, and her lighthearted reaction won her new beau over. “She thought it was the funniest thing, and I was like, ‘I’m marrying this chick,’” he said, adding, “That’s what sealed the deal of us deciding to get married. And since then, we’ve lived in wedded bliss.”

2006: Coming Clean

After spending roughly two-and-a-half months of keeping their love under wraps, Olson and McElhenney decided to let their castmates in on their little secret. “At the end of [season 2] we came clean,” Olson later told the New York Post.

Costar Mary Elizabeth Ellis, who played the waitress on the show, remembered the conversation to Buzzfeed in 2015. “They were like, ‘We have something to tell you guys,’” she said. “Kaitlin just starts crying and says, ‘I love [Rob.] I love him so much, you guys. He’s such a great person. We don’t want you guys to be mad at us because we’re dating and on the show.”

Luckily, the pair needn’t have worried. “It just made us laugh so hard, because it was such a funny way to reveal that they were dating for the first time,” Ellis said, adding, “They’re just so great together.”

2007: Popping the Question

After nearly two years together, McElhenney got down on one knee to propose at It’s Always Sunny costar Danny DeVito’s Malibu beach house. “She loves the beach when it’s cold,” the groom explained to InStyle in 2015.

As for the ring, the Mythic Quest star chose a vintage diamond cocktail ring from the 1920s for his bride-to-be.

September 27, 2008: Tying the Knot

The lovebirds exchanged vows at a Malibu vineyard in the fall of 2008. Apart from their guest list, which was attended by several Hollywood heavyweights, including Danny DeVito and Emily Deschanel, they kept things mostly low-key with a nature-inspired reception and Earth-friendly décor. "We wanted our wedding to produce as little waste as possible,” Olson later told InStyle.

As a result, the couple opted for potted plants, herbs and vegetables over cut flowers, with pastoral arrangements of geranium leaves, eucalyptus, hypericum berries, and artichokes to line their reception tables. Their four-tier cake was also right on theme with sugar grass leaves and buttercream lily of the valley flowers, and the bride walked down the aisle in a gorgeous cotton-and-lace off-the-shoulder gown by Les Habitudes.

They also had an unexpected guest while saying their “I dos.” “We were told that a white stallion galloped past as we were saying our vows,” Olson told Dax Shepard on a 2018 episode of the actor’s podcast, “Armchair Expert.“

July 27, 2009: Stepping Out

The married couple had date night on the red carpet for the 2009 premiere of Julie & Julia in L.A.

Rob McElhenney wraps his arm around wife Kaitlin Olson on the red carpet.

Jon Kopaloff/Film Magic/Getty Images

March 2010: A Pregnancy Announcement

People reported that the twosome were expecting their first child in March 2010.

May 2, 2010: It’s a Boy

Olson debuted her growing baby bump on the red carpet while attending a Pregnancy Awareness Month kickoff event in Los Angeles alongside her husband on May 2, 2010. At the event, the comedians revealed to People that they were expecting a baby boy. “You’re just happy that all of his little fingers and toes are there," Olson joked. "And he’s really handsome, I’ll tell you that much. We’ve seen pictures!”

A pregnant Kailtin Olson wears a striped dress on the green carpet next to husband Rob McElhenney

Michael Kovac/Getty Images

September 1, 2010: The Family Grows

On September 1, 2010, Olson and McElhenney became first-time parents when their son, Axel Lee McElhenney, was born at 12:52 in the afternoon. “I went into labor at the Phillies/Dodgers game on Tuesday night,” the new mom told People of her at-home childbirth. “As soon as Ryan Howard hit a three-run home run, we felt comfortable leaving to go have our baby. We love him like crazy, even though he made us miss the second half of the game.”

Luckily, Olson, who had hoped to deliver at home, had been rehearsing for just such an occasion. “I’ve been practicing hypnobirthing for several months now. It’s basically training yourself to completely relax on command, allowing your uterus to do its job without tensing up in reaction to the pain, which just slows everything down,” she told People in August 2010.

Needless to say, the new parents were over the moon. ““Rob and I are so excited it’s stupid,” Olson told the magazine. “The last couple years have been pretty amazing for us and just when we thought things couldn’t get any better, the greatest little thing in the world happened! We’re totally beside ourselves.” She later revealed the inspiration for their baby's name to Spin, saying, “We thought the name was cool, and then someone reminded me of Axel Foley from Beverly Hills Cop and I was on board.”

October 27, 2011: Baby on Board

The happy couple not only revealed that they were expecting once more in an interview with People in 2011, they shared the baby’s sex with the outlet, saying, "We're having a boy! We're so happy that Axel gets to have a brother so close in age.” Olson then added, “And that I get to add another set of balls to my very, very male world.”

According to the Mick star, news of her pregnancy came during a birthday celebration for her mom in Ojai, California. “I was instantly so proud of this baby for already knowing how to make someone else's special day all about him,” she joked.

April 5, 2012: Bundle of Joy

The Riches actress revealed that her and McElhenney’s son had made his way into the world in a Tweet on April 9, 2012. “Leo Grey McElhenney,” she captioned the first photo of the sleeping babe. “Born April 5th after 23 very, very long hours. We’re in love.”

August 2, 2018: Teaming Up

Olson and McElhenney teamed up on a new project in August 2018 for a TV movie co-written by the actor that would come to be called Mean Jean.

August 18, 2019: A Shining Light

McElhenney called his wife “light in human form” (in all caps, no less), while wishing her a happy 44th birthday in 2019. “Every day you teach me about kindness, patience, forgiveness, and inconceivable resilience,” he wrote via Instagram.

The writer also addressed the rawness of their relationship, saying, “Instagram relationships seem to be perfect. We don’t have one of those. It’s messy and hard and wonderful and boring and sweet and exciting and miserable and joyous. I don’t know much but I know this... I am lost without you.”

Sept 27, 2019: Major Milestone

For the couple’s 11th wedding anniversary, McElhenney shared some sweet lyrics from Kenny Rogers’ song “Through the Years,” along with a series of unflattering-yet-hilarious photos of his spouse. “Happy 11th Anniversary, my love,” he captioned the pics. “Let’s do fifty more. Because in the end, we gotta die somehow. It may as well be laughing.”

August 18, 2020: Birthday Laughs

McElhenney shared a steamy photo of his other half on Instagram for her birthday in 2020, writing, “Whoa. This woman married ME? She’s the funniest person on Earth. AND the best Mom. She could mate with anyone she wanted.”

He then added a cheeky punchline, writing, “She’s clearly got low self esteem. Happy Birthday @kaitlinolson!!!”

April 13, 2021: Golden Boy

Olson wished her spouse, whom she called the “the Goldenest of all the Gods,” a happy birthday on Instagram in April 2021 while simultaneously making a few good-natured jokes. “I love you. And I really love the hair you used to have but don’t anymore.☝🏼” she wrote. “You still have the same great smile, though, so that’s pretty cool! I know this because when we are together, you’re always laughing. I’m very, very funny. Happy birthday!!!"

December 22, 2021: The End of an Era

After 16 years on the air, It’s Always Sunny in Philadelphia had its final episode, ending the couple’s first-ever joint project.

The Cast of "It's Always Sunny in Philadelphia"

Tibrina Hobson/Getty Images

August 10, 2022: Dynamic Duo

Olson and McElhenney appeared alongside each other on Jimmy Kimmel Live! on August 10, 2022, with McElhenney serving as the show’s host in Jimmy Kimmel’s absence and Olson guest-starring. The Emmy nominee took the opportunity to address a few beefs with her spouse, saying, “You remember that clip you showed earlier…where we were all in England celebrating what we thought was, you know, a goal…” a clip then plays of Olson standing up and turning around to give her husband a hug, who instead turns to Ryan Reynolds beside him.

“Here I am, turn around to, you know, congratulate my husband, and you just go ahead and jump right into the arms of Ryan Reynolds. Just aggressively. You saw me! And you turned, and you jumped, right into his arms!” she said incredulously. “In fairness,” McElhenney replied, “who wouldn’t want want to jump into the arms of Ryan Reynolds? I didn’t want to hurt you.”

The couple continued to make playful jabs back and forth at each other (“How did this become a roast? This is a very clear glimpse into what our household is like,” McElhenney protested), but had several earnest moments, the first of which began when he took time out to congratulate his wife on her 2022 Emmy nomination for Outstanding Guest Actress in a Comedy Series for Hacks.

Later in the show, McElhenney gushed, “Being in a relationship is very difficult. We’ve had our ups and downs, we’ve been married for, coming up on 14 years this September. And I can tell you that I love you more now than I did 14 years ago. And that for as hard as it is sometimes, just like in any relationship, I will keep showing up and doing my best, because I love you so much.”

August 18, 2022: Birthday Roast

For his annual birthday roast, McElhenney shared a throwback photo of a heavily permed Olson, writing, "I love this woman more than she loved her Aqua-net in 1988. Happy birthday you awkward ass beautiful perfect specimen."

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