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How to wear: An older man

Hollywood hates equality. Men date young; women marry up. But before you snort in disgust, know that Lauren Bacall was a mere 19 when she first started dating 45- year-old Humphrey Bogart. “He was very apprehensive about the age difference, but it didn’t bother me,” she has said of the onset of their 13-year relationship. Nowadays, a 25-year age gap amongst men and women isn’t shocking. (Tabloids recently linked Nicole Richie and Jeff Goldblum.) “If I have a 50-year-old client who wants to date a 25-year-old, you bet I am going to ask, ‘Why?'” says Samantha Daniels, of Samantha’s Table Matchmaking. For women seeking the older set? “The novelty of the fact that you know all about hip-hop will wear off. You need to brush up on his interests, too.”

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