TBT: Mandy Moore Was Set Up With Andy Roddick by Her Mom

Who: Emmy-nominated actress, singer, and songwriter Mandy Moore, 39, and former tennis pro Andy Roddick, 40. 

How They Met: The athlete and actress met on the set of the romantic comedy How to Deal in 2002 — thanks to Mandy’s mom, Stacy Moore, who played matchmaker. 

"About the last three weeks of the film, I meet this guy who completely just steals my heart. I'm so happy and crushing on him. I have mom to thank for that,” Mandy said during an interview with The Early Show, explaining that her mom, a former journalist, managed to get in contact with Andy and invited him to meet Mandy while she was filming in Canada. 

She continued, “Luckily, Andy obliged, accepted the invitation and came and met me on the set. I watched his tennis match the next day and the rest is history, I guess." 

That history would include red carpet premieres, low-key hangs, and many, many tennis matches.  

Why We Loved Them: Moore and Roddick were both young, incredibly good-looking, and on the come-up of their respective careers when they first started dating (Mandy had just made the switch from singing to acting, while Andy was a promising tennis superstar) — the prime makings for an early 2000s It couple.

Plus, the fact that their names rhymed was an added bonus. 

When They Peaked: When Andy won the 2003 U.S. Open (his first and only grand-slam title) while Mandy cheered him on from the stands.

The Breakup: After dating for about a year and a half, Mandy and Andy decided to call it quits on their relationship in March 2004.

While the details surrounding their split were scarce, Mandy revealed that the breakup hit her hard while speaking with Howard Stern about it 14 years later. "He broke my heart, Howard," she said. "So, I think we parted ways because of that. [The heartbreak] got poured into everything. It got poured into a record that eventually became an album that came out like three or four years after that." Mandy was seemingly referring to her Wild Hope album, which includes a song about a man being unfaithful titled "Ladies Choice."

Mandy then cryptically hinted about Andy cheating, saying that all men "get a wandering eye," adding: "It’s human nature, part of the human condition. You’re on to the next! It’s OK, wasn’t meant to be.”

But there's no hard feelings between herself and Roddick — anymore, at least. “He’s like married with kids and he seems super happy, and I’m happy for him," Mandy explained. "We were kids; I don’t care. Ten years ago, I would have had an axe to grind, but now I’m like whatever.”

Where They Are Now:  After Andy, Mandy soon began dating Zach Braff, before having two short flings with DJ AM (Adam Goldstein) and singer-songwriter Greg Laswell. In 2009, she married indie rocker Ryan Adams, but the pair didn't last and divorced six years later. Mandy is now married to musician Taylor Goldsmith and the couple share a two sons, August "Gus" Harrison, 2, and 9-month-old Oscar "Ozzie" Bennett.

As she did in the past, Mandy continues to balance music and an acting career. While wrapping up the final season of the Emmy-winning series This Is Us in 2022, Mandy also released a new album called In Real Life that same year.

Following his split from Mandy, Andy was reportedly dating fellow tennis legend Maria Sharapova. However, their rumored romance fizzled within a few months, and Roddick then had a brief romance with Paris Hilton. By 2007, he met his now-wife Brooklyn Decker and they welcomed two children during their marriage — a son, Hank, and a daughter, Stevie.

In 2012, Andy retired from professional tennis following the U.S. Open to focus on his work at the Andy Roddick Foundation. But he didn't completely quit playing the sport all together. During retirement, Andy played for the Austin Aces in World Team Tennis and won two championships in the QQQ Champions Series.

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.