Actress (upcoming movies include Boat Trip, with Cuba Gooding Jr., and Basic, starring John Travolta and Samuel L. Jackson); 29
Date Style: "Maybe it's a Latina thing—I like to look sexy." She won't go out without high heels. "I feel leaner and taller in them."
First-date advisory: "If a guy says, 'I wasn't faithful to my last girlfriend,' pay attention. Don't think you can change him."
Matchmaker feedback: "Wearing color makes you seem more accessible," says Samantha Daniels (her company, Samantha's Table, not only fixes people up but coaches them on their social life). "These shades are soft and spring-like and look good with Roselyn's skin and hair."
Suede corset top, $150, Andrew Marc. Silk skirt, $850, Ralph Lauren Collection. Ring, Baccarat.
Jana Marie Hupp
Actress (she plays Nancy Burton on NBC's Ed); 38
Date style: "I don't ever dress up for a date—in fact, I don't even call them dates: We just hang out and see if we want to go out someday." She likes low-slung jeans, vintage tees, boots: "I generally am who I am, take it or leave it."
First-date advisory: "Meeting a guy—the Cinderella thing—isn't the be-all and end-all. It's a big mistake to tailor yourself to the man. You'll make yourself schizophrenic."
Matchmaker feedback: This eclectic mix—a cropped Chanel jacket with jeans—gives a sense of Jana Marie's fashion panache as well as a glimpse of bare stomach. Samantha says, "Showing a little bit of skin is fine."
Wool jacket, Chanel. Cotton tank, $145, Philosophy di Alberta Ferretti. Jeans, A Gold E. Beaded scarf (as necklace), Chan Lu at Fragments.