Ben Stiller and Christine Taylor's Relationship Timeline

After a five-year separation, Ben Stiller and Christine Taylor are giving their romance another go.

The couple first met in 1999 and wed less than a year later, with Stiller telling Entertainment Tonight in 2007 that he knew pretty quickly she was "the one." According to the comedian, "When I met her, I pretty much thought, 'That's the person.' It was like, 'Wow, this is a great person. I love her.' "

The pair went on to collaborate on multiple films, working together on Zoolander, Dodgeball: A True Underdog Story, Tropic Thunder and Zoolander 2.

They also welcomed two children, Ella Olivia and Quinlin Dempsey, in 2002 and 2005. The duo remained low-key until they announced their separation in May 2017. After they were spotted together multiple times after their split, the couple announced they were reuniting in February 2022.

From sharing screen time to a brief separation, here's everything to know about Ben Stiller and Christine Taylor's relationship.

1999: Ben Stiller and Christine Taylor meet for the first time filming a TV pilot

The pair first met while filming a TV pilot called Heat Vision and Jack, which ultimately never made it to air.

In 2016, Stiller opened up about how their first meeting quickly turned into a first date, telling Parade, "I was directing a pilot for Fox, starring Jack Black, called Heat Vision and Jack [1999]. My wife came in to audition for the role of the sexy sheriff. She had been in the Brady Bunch movies and they were pushing her on me. She came in and she was great … I was single. I'd come out of a long relationship with [actress] Jeanne Tripplehorn. Christine was coming out of a relationship too. We went on a date and it clicked. We were both on the rebound. And we just jumped."

June 5, 1999: Christine Taylor and Ben Stiller make their first public appearance at the MTV Movie Awards

Taylor accompanied Stiller to the 1999 MTV Movie Awards, where he was up for four awards for his role in There's Something About Mary. Of their budding romance, Stiller told Parade in 2013 that their relationship "was a gradual thing that happened over a quick period of time, maybe seven or eight months."

"We just started hanging out with each other and it developed into, 'Wow, this feels great. I really like this person. I think I love this person. I really do — I love this person,' " Stiller continued. "It hit me out of the blue."

May 13, 2000: Ben Stiller and Christine Taylor get married in Kauai, Hawaii

PEOPLE reported that the couple tied the knot at an oceanfront residence in Hawaii after a six-month engagement. Of their romance, Stiller told Parade in 2016, "We got married pretty quickly. I turned around one day and said, 'Wow, I'm happy with her. We connect. I'm enjoying being with her all the time!' It just felt right."

Of their engagement, the Severance director told Parade in 2013 that it mirrored his on-screen proposal in Meet the Parents. "I proposed to Christine when I was rehearsing Meet the Parents ... I asked her father for permission before I did it ... It was like Meet the Parents in real life, because Christine's father is an intimidating guy who owns a security company; we're good friends now, but at the time I was in the basement rec room saying, 'I really would like to marry your daughter …' He's a man of few words but he was very welcoming. I was more nervous asking him than asking her."

September 2001: Christine Taylor stars as Ben Stiller's love interest in Zoolander

Marking their first big screen collaboration, Taylor starred as Stiller's love interest in the cult comedy Zoolander, playing journalist Matilda Jeffries to Stiller's titular male model.

April 9, 2002: Ben Stiller and Christine Taylor welcome their first child

Taylor gave birth to the couple's first child, daughter Ella on April 9, 2002. In 2004, Taylor told PEOPLE of their daughter: "It's not even funny how much (Ella) is like Ben. She's definitely a ham."

In 2013, Stiller told Parade of becoming a new dad: "When your wife is pregnant for nine months, you get used to the idea of pregnancy. Obviously, you know where it's leading, but it almost becomes this abstract idea; and then suddenly the next time you go back to the house, you have another person living with you. Who you've just met. Your child … I was thinking moment to moment: Just get her from the baby carrier to the crib … It's a short distance but a huge change."

June 2004: Christine Taylor and Ben Stiller appear in another movie together

Taylor and Stiller made their second big screen appearance together in Dodgeball: A True Underdog Story. Of their roles in the comedy, Stiller told IGN in 2004, "It was fun. We had fun, we were laughing a lot, we got to spend time together which was good. When you're working, you don't get to do that. And she, we just connect on that level … We laugh at the same things, so it was actually really fun and therapeutic. It's always good to throw balls at each other. It would be good therapy, good couples therapy."

"It was just a great experience all round," Taylor added. "I mean, we had a blast." She also noted it was a "very different dynamic" than when they filmed Zoolander prior to becoming new parents.

"This is the first movie we did together since having our daughter, so there were endless challenges personally," said Taylor. "When we did Zoolander, we were newly married … It was sort of almost an extended honeymoon."

July 10, 2005: Ben Stiller and Christine Taylor welcome their second child

The couple welcomed their second child, a baby boy named Quinlin, on July 10, 2005.

In 2009, Stiller explained to PEOPLE that Quinlin completed their family. "Two is a handful. I feel very fortunate and blessed," he said.

August 2008: Christine Taylor and Ben Stiller team up again for Tropic Thunder

Stiller tapped his wife to join him on-screen again in 2008's Tropic Thunder, which he wrote, directed and acted in. Taylor starred as herself in the hit comedy.

After the film's premiere, the Search Party star took time off from her acting career to focus on the couple's family, with Stiller telling Parade in 2016: "She made the choice to be a mother first to our kids. A few years in, she said, 'I think this is what I need to do.' She felt she needed to be there. I feel very fortunate for our kids."

December 2010: Christine Taylor opens up about her semi-retirement and being a mom to her kids with Ben Stiller

In an interview with The Morning Call for her Scrooge-inspired role in the TV movie Farewell Mr. Kringle, Taylor joked that she "didn't have to do a whole lot of research," adding, "I think if you ask my husband, he'd say that he's seen this side of me every now and again. Believe me, I have my moments."

Of taking some time to be back on set, Taylor called it "the perfect time" as Stiller had been on a break between films. "It was really the first time that I could even think about working because Ben could take on the mom responsibilities."

"It never felt like a big decision for me," she said of taking time away from her career to raise her kids. "It happened so naturally. When I married Ben, I just decided to go with him. He travels so much. It was a no-brainer. I wanted to be with him. And sometimes I got to be in his movies and work with him, which I loved."

She continued, "Then, when I had Ella, my whole world changed. I couldn't believe how much love I had for this little creature. I wanted to be a part of it all. I didn't want to miss anything, and with Ben working as much as he does, I felt it was important for one of us to be the stability in the family."

February 26, 2011: Ben Stiller talks about his ideal movie night with Christine Taylor

In a red carpet interview at the 2011 Independent Spirit Awards, the Greenberg star shared that his dream movie night involves none other than Taylor. "I like my movie nights with my wife, that's my favorite. When you have kids — when you have date night — movie night is a very exciting thing for a married couple, so definitely my wife," he said.

September 3, 2012: Christine Taylor reveals Ben Stiller's "competitive" streak

Though they might enjoy curling up on the couch for a movie night in, it seems Stiller can get a bit competitive when they're up against each other in sports. During an interview at the 2012 US Open, Taylor shared that her husband is "by far more competitive" in tennis, and usually he'll win. But she beat him at miniature golf, adding, "I always find that the less competitive you are in your own mind, the better you play, if you're just relaxed."

In 2013, Stiller told PEOPLE about one ill-fated tennis match. "I lost [my wedding ring] in my wife's handbag. I took it off to pick up a tennis racket and put it in her bottomless pit without telling her. A couple of hours later and it had already disappeared into the universe."

December 2013: Ben Stiller tells PEOPLE how Christine Taylor keeps him calm

The actor told PEOPLE of Taylor's calming advice when things get hectic. "My wife is usually very good at giving me advice. I've been working a lot lately, and she said to just take a breath. Breathe and take it one day at a time," he explained.

October 2014: Christine Taylor and Ben Stiller discuss their relationship

Making a joint appearance at the 16th annual Tomorrow Is Tonight Gala Benefiting Project A.L.S. in New York, the couple chatted with PEOPLE about how their relationship has evolved over the years.

"It's all change for the better. Right? We're older, we're wiser," said Taylor, with Stiller agreeing, "We're hopefully getting better." She added, "I found a picture of us from 15 years ago, and I saw youth. You don't see [the change] on a daily basis. We looked like kids. Now we look like parents."

February 2016: Ben Stiller and Christine Taylor team up together again for Zoolander 2

Fifteen years after Blue Steel, the couple reprised their roles in a sequel to the 2001 comedy, teaming up to share directing duties. In an interview with Rachael Ray, Taylor joked: "He knows what he wants, and he's very serious about it, but when he's directing you in a wig and ridiculous shirt ... it's very hard to take him seriously."

May 26, 2017: Christine Taylor and Ben Stiller announce their separation

The couple announced their separation on May 26, 2017, telling PEOPLE in a joint statement: "With tremendous love and respect for each other, and the 18 years we spent together as a couple, we have made the decision to separate. Our priority will continue to be raising our children as devoted parents and the closest of friends. We kindly ask that the media respect our privacy at this time."

2018: Ben Stiller and Christine Taylor are spotted together multiple times after their split

Throughout 2018, the former couple were spotted together during several outings, including getting dinner in Manhattan, at the 2018 US Open with daughter Ella and at the 2018 Project ALS Gala with both their children.

April 8, 2019: Christine Taylor and Ben Stiller are spotted holding hands during a family outing

An onlooker told PEOPLE the pair were holding hands during a family outing to see Pretty Woman: The Musical on Broadway, where they also posed for photographs backstage.

September 22, 2019: Christine Taylor poses with Ben Stiller on the red carpet at the 2019 Emmys

Taylor attended the 2019 Emmy Awards to support Stiller, where he was nominated for outstanding directing for a limited series, movie or dramatic special for Escape At Dannemora.

October 2020: Ben Stiller produces Friendsgiving starring Christine Taylor

Stiller served as a producer on the holiday comedy Friendsgiving, which Taylor starred in.

February 2022: Ben Stiller reveals he and Christine Taylor reunited during the pandemic

In an Esquire interview, Stiller revealed that he and Taylor reconciled after he moved back in with Taylor and their children during the pandemic. He said their relationship "evolved" over the course of time, noting, "We were separated and got back together and we're happy about that. It's been really wonderful for all of us. Unexpected, and one of the things that came out of the pandemic."

Of their relationship, Stiller said, "I think we have respect for the ways that we're similar and the ways we're different. And I think accepting that, you can really appreciate someone more because you're not trying to get them to change for you."

"Once you accept that, you save a lot of energy," he continued. "'This is something that works for me; this is something that doesn't work for me.' If you have that trust level with your partner, you know that me saying 'I don't like doing that thing' is not me saying 'I don't like you.' "

At the time, a source told PEOPLE the couple were "never estranged" during their separation, and another source shared that Stiller leaned on Taylor after the death of his father, actor Jerry Stiller, in 2020.

March 18, 2022: Christine Taylor and Ben Stiller attend the BNP Paribas Open together

The longtime tennis fans made their first public appearance since announcing their reconciliation at the BNP Paribas Open in Indian Wells, California, sitting side-by-side in the stands.

August 30, 2022: Ben Stiller and Christine Taylor attend the US Open

A few months later, Stiller and Taylor were all smiles while attending another tennis event. The pair took in a match at the US Open at the Billie Jean King National Tennis Center in New York City.

November 13, 2022: Ben Stiller and Christine Taylor enjoy a Broadway date night

Stiller and Taylor attended the opening night of comedian Mike Birbiglia's The Old Man & the Pool on Broadway. The pair looked happy as they smiled and wrapped their arms around each other on the red carpet.

For the outing, Stiller wore a dark coat over a blue button-up, black slacks and gray sneakers. Meanwhile, Taylor was photographed in an all-black ensemble, accessorized with a tan belt.

January 2023: Ben Stiller guest stars on Christine Taylor's podcast

Stiller made an appearance on Taylor's podcast Hey Dude... The 90s Called! The series, which premiered in December 2022, features Taylor and her co-host, David Lascher.

"So, it's been really fun," Stiller told PEOPLE. "I had a great time doing the episode, and it's fun to be a part of something new that they're just getting off the ground, and it seems to be off to a really great start."

March 7, 2023: Christine Taylor reveals details of her and Ben Stiller's split and reconciliation

Taylor spoke about her relationship with Stiller during an appearance on The Drew Barrymore Show.

"Family was always a priority, but I think Ben and I both started to grow in different directions," the actress told host Drew Barrymore. "And when we made the decision to separate, it was not something we wanted to talk publicly about or took lightly."

She added that, at the time of their separation, she and Stiller "were at this impasse of, 'Let's figure this out — what's best at this chapter in our lives?' "

"I think we have these growth spurts, even as adults. And we needed time to figure that out," Taylor added.

June 11, 2023: Christine Taylor and Ben Stiller attend the Tribeca Film Festival

Taylor attended the premiere of her film Let Liv at the Tribeca Film Festival. She was joined by Stiller and their daughter, Ella. The trio, who looked effortlessly chic in coordinating black ensembles, posed together for photos on the red carpet.

October 26, 2023: Christine Taylor and Ben Stiller host the 25th Project ALS Anniversary gala

The couple hosted the 25th Project ALS Anniversary gala at the Lincoln Center in New York City. Stiller and Taylor were joined by their son, Quinlin Dempsey.

“We really do enjoy hanging out as a family. Watching movies, playing silly tennis," the Night at the Museum star told PEOPLE on the red carpet.

January 28, 2024: Christine Taylor and Ben Stiller attend a Broadway show

The couple, who were joined by their daughter, Ella, attended a performance of the Broadway musical Harmony. Following the show, the trio went backstage to meet members of the cast.