Luke Grimes' 'Daring' Pickup Line on Diaz & Barrymore

During a recent appearance on The Drew Barrymore Show, Yellowstone star Luke Grimes reminisced about a memorable encounter from approximately twenty years ago. He revealed that he once attempted to flirt with both Drew Barrymore and Cameron Diaz at a club in Los Angeles. Grimes explained that a friend dared him to approach the actresses, who have maintained a close friendship since starring together in Charlie's Angels.

Grimes recalled working up the courage to speak to Barrymore and Diaz, ultimately delivering a pickup line. He described their amused reactions to his attempt, noting that Cameron Diaz's response felt very much in character. Drew Barrymore expressed her appreciation for his effort, finding the story charming even after two decades. The anecdote highlights a lighter, earlier chapter in Grimes' career before his prominent role on Yellowstone.