Ben Stiller and Christine Taylor initially cross paths in 1999 while filming a television pilot. At the MTV Movie Awards on June 5, 1999, Christine Taylor and Ben Stiller make their first appearances.

Ben Stiller and Christine Taylor exchange vows on May 13 in Kauai, Hawaii.Christine Taylor plays Ben Stiller's love interest in the September 2001 film Zoolander.

Ben Stiller and Christine Taylor welcome their first child on April 9, 2002.Christine Taylor and Ben Stiller co-star in a different film in June 2004.

Ben Stiller and Christine Taylor welcome their second child on July 10, 2005.Ben Stiller and Christine Taylor reunite in August 2008's Tropic Thunder.

Christine Taylor discusses her parenting roles and semi-retirement with Ben Stiller in December 2010. Christine Taylor reveals Ben Stiller's "competitive" streak on September 3, 2012.

Ben Stiller reveals to PEOPLE in December 2013 how Christine Taylor helps him stay composed Christine Taylor and Ben Stiller talk about their romance in October 2014

Christine Taylor and Ben Stiller reunite for Zoolander 2 in February 2016. Ben Stiller and Christine Taylor announced their separation on May 26, 2017.

Ben Stiller and Christine Taylor have been sighted together several times in 2018 following their breakup. They were seen holding hands on April 8 while out with their families.

Christine Taylor and Ben Stiller take a photo on the Emmys red carpet on September 22, 2019. Ben Stiller presents Friendsgiving in October 2020 with Christine Taylor.

Ben Stiller confesses in February 2022 that he and Christine Taylor got back together during the pandemic. 

Christine Taylor and Ben Stiller go to the BNP Paribas Open together on March 18, 2022.

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