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The American Idol champ, 24, and the Gossip Girl actor, 22, stopped at restaurant Destino earlier in the night before following up with more food, drinks and dessert at the pop star's restaurant. The pair ate BBQ wings, Timberlake's "Grannie's Pecan Pie" and looked "pretty lovey dovey," according to an observer.
They were spotted again on Wednesday, when he watched Underwood perform on Live with Regis and Kelly. A source tells PEOPLE that one person surprised to see Crawford backstage was his own Gossip Girl costar Blake Lively, who was also a guest.
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