Thirty-year-old Jessica has been on 100 first dates and she's still single! She thinks her confident personality is off-putting to men--but it's her sloppy style that's sending all the wrong messages. Her don't-care, comfy wear makes it seem as if she doesn't take pride in how she looks--and that's hurting her in the love department. Jennifer is ready to find Mr. Right, but her hideous clothes are standing in the way. Watch as stylist Jeannie Mai schools her on the fashion laws of attraction and gives her a look that says, "I'm single and ready to mingle!"