Patrick Dempsey and Jillian Fink (Hairstylist and Makeup Artist)
Patrick Dempsey fell in love with his hairstylist, Jillian Frank, and married her in 1999. The Grey’s Anatomy star who plays Doctor Derek Shepherd, aka “McDreamy,” is said to have shed tears of joy on his wedding day as his wife walked down the aisle. While the couple has been able to keep their family together over the years, they were on the brink of splitting just a few years ago.
“Our marriage was not something I was prepared to let go of,” Dempsey revealed in an interview. “I didn’t feel like we had done all the work. And we both wanted to do that work. That’s where it started.” They’ve since been able to work things out and continue to focus on their relationship as well as their family. Together the couple has three children.
Tobey Maguire and Jennifer Meyer (Jewelry Designer)
Tobey Maguire met jewelry designer Jennifer Meyer, a longtime fan of the actor while filming Seabiscuit at Universal Studios. Meyer is the daughter of Ronald Meyer, the former president and CEO of Universal Studios, and was hardly a stranger to the Hollywood lifestyle. Best known for his roles in Spider-man , Fear and Loathing in Las Vegas , and The Great Gatsby, Maguire met Meyer in 2003 and the pair tied the knot in Hawaii just three years later after the birth of their first child.
The couple had their second child in 2009, but unfortunately, the relationship didn’t last. Although Meyer has gone on record saying Macguire is a fantastic father, the couple ended their marriage after nine years together. They were divorced in 2017.
Conan O'Brien and Liza Powel (Ad Rep)
Comedian Conan O’Brien said he fell in love with his now-wife, Liza Powel the very moment he saw her in the audience while he was taping an episode of his show, Late Night With Conan O’Brien . His now-wife, Liza Powel, appeared on the show in an advertising skit involving Foote, Cone & Belding, where she was working as senior copywriter.
The couple dated for just 18 months before they tied the knot in 2002 in Powel's hometown of Seattle. When asked why he fell in love with his wife, the talk-show host said it was because she is extremely beautiful and that she happens to be a very good person. The pair now have two kids together.
Kelsey Grammer and Kayte Walsh (Flight Attendant)
Kelsey Grammer met Kayte Walsh, a British flight attendant, as she served him coffee at 35,000 feet. While the two didn’t exactly join the mile-high club, they spent a romantic evening in London just a few days later. Although the pair met while Kelsey was still married to Real Housewives of Beverly Hills star Camille Grammer, their affair went on for six months.
Grammer allegedly ended his marriage in a text message, marrying Walsh just 15 days after his divorce was finalized. Even though his third marriage went up in flames in front of millions of people on TV, his ex-wife, who has often expressed her resentment towards the couple, has since moved on. Grammar and his new wife are currently happy and enjoying their marriage.
Matt Damon and Luciana Barroso (Bartender)
Matt Damon met Luciana Barroso while he was filming Stuck On You in 2003. Damon stopped at a bar in Miami on his night off where he noticed Barroso bartending. It was love at first sight and the two have been joined at the hip ever since.
The duo married a few years after meeting and their relationship has only grown stronger since then. While raising their four kids, Isabella, Stella, Alexia, and Gia, the couple has maintained a relatively private life. The actor’s life is practically a real-life rom-com!