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She was a nationally recognized steeplechaser by her first year at Columbia, when a friend introduced her to Tom Higgenson, the lead singer/songwriter for a new indie pop group, the Plain White T's.
It was released in May 2006 as the third single from their third studio album All That We Needed.
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I don't think it'll be awkward, but it'll be interesting.
I've never been on a date that has been this high-profile." Still, we reckon he's done his groundwork - it's not many guys who go to the trouble of baring their soul to millions of people before asking a girl to hang out.