Judy McGuire's been writing the Dategirl column for Seattle Weekly for six years and has a brand new book out called "How Not To Date". Over the years, she's advised readers on everything from breakups to orgasms to cohabitiation, escort etiquette and Daddy issues. She'll only own up to being "older than Shakira, younger than Madonna," but has certainly seen and heard a lot.  Whatever your problem, she's likely been there and done that multiple times. Send your dating and relationship questions to theladiesroom@movin925.com.