Alva Chinn
Model, Actress, Entrepreneur; 52

Date style: "As a tall woman who speaks her mind, I can be intimidating," Alva says. So she softens the effect with a feminine dress, "or a top that says I have curves. I believe in showing what you've got." Jeans? "Only if I'm going bowling."

First-date advisory: "Be yourself, because it would require too much work to do anything else."

Matchmaker feedback: "There is a subtle suggestion of flirtatiousness here," says Samantha. "This dress has a lot of movement, and the color brings out Alva's natural rosiness. She seems happy and approachable."

Floral chiffon dress, $340, Diane von Furstenberg. Earrings, $320, Nava Zanavi. Gold necklace, Gold Avenue. Shoes, Anne Klein.