Ladies: What would you do if you had to start over in the dating game in your 40s, 50s or even 60s? Dr.Phil’s guests say there is a double standard that middle-aged men can date women young enough to be their daughters, but yet it’s considered inappropriate for middle-aged women to date much younger men. Caroline is a 58-year-old grandmother who has been married three times and is still looking for her Prince Charming. She admitst o traveling from Monaco to Amsterdam and throughout the states in search of love, often with younger men. Caroline says she even accepted a proposal from a man she met online -- a suitor she has never met in person! Her daughter, Anara, says the problem is not her mother’s age, but that her mom doesn’t act her age. Is Caroline just living life without limits, or is she her own worst enemy when it comes to meeting Mr. Right? Then, Dr. Phil talks to Patti Stanger, CEO of The Millionaire’s Club, an exclusive dating service that caters to wealthy men and women who are looking for love. Find out why Patti says Caroline is heading toward a life of loneliness, and learn her 10 Commandments of Dating -- for Women to increase your chances of finding a mate. And, Anna is only 30, but she says some men already think she’s too old to date! Her friend, Robyn, says men are sometimes turned off by Anna's independence. Find out what happens when Dr. Phil cameras follow Anna for a night on the town. Plus, meet a divorced mom who says she’s been on the dating scene for 15 years and has yet to find a man her age who wants to commit.

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