Inside Mandy Moore’s Long, Winding Road to Happily Ever After

Her romantic life started off easily enough.

Despite having weathered splits from Valderrama and Roddick before she exited her teens, Moore declared in a 2003 interview with PBS, “I haven’t had too much trauma with love. I’m sure it’s coming sometime because you can’t escape it. I feel like I’ve come off unscathed so far.” 

Already wise at 19 she was, of course, right. In 2006 she would listen in horror as Valderrama recounted their sweet, teenage love story—for their first date at Santa Monica’s Ivy at the Shore, he picked her up from the W hotel where her mom informed him she’d nervously changed her shirt three times—to shock jock Stern. 

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Pressured to share more beyond their meet-cute (they were shooting the cover of Teen magazine) and how they “were each other’s first loves,” he finally relented as Robin Quivers and Artie Lange joined Stern in asking about their sex life, each demanding to know if he was her first, you know, everything. Having already ranked his previous paramours and spoken about his, er, stature, he said this about supposedly taking Moore’s virginity, “Honestly, I think everyone’s going to relate to this, but…I will say this: it is not like warm apple pie…Let’s see, how do I put this in the most [politically correct] way possible—it’s just really good.” 

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