You’re smart, sexy and sweet — so why are you still single? Dr. Phil and expert matchmaker and host of VH1's Why Am I Still Single?, Siggy Flicker, strive to answer that question for two struggling daters. Paul, 39, says he’s tried to meet women at church, through a mail-order bride service, and even held up a sign on the side of the road — but every time falls flat on his face. Can Dr. Phil and Siggy help this lonely bachelor find his dream girl? And, Marilyn, 40, lost a dramatic 129 pounds since she last appeared on Dr. Phil and says she’s finally ready to play the field. Get a birds-eye view as these daring daters are set up with potential suitors — and each other! Will there be a love connection?

Lost in Love

Paul says he's been nothing but unlucky in love. And while his dating antics have provided good fodder for funny storytelling, Paul says his love life is no laughing matter. Will a social experiment shed light on where Paul has gone wrong? Then, Marilyn has lost a whopping 129 pounds since first appearing on Dr. Phil, but says she's also lost at something else — love. With the help of expert matchmaker and host of VH1's Why Am I Still Single? Siggy Flicker, Dr. Phil gets to the bottom of these guests' dating woes?

“Rejection is God’s protection — taking someone that wasn’t right for you and moving them out of the way.”

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A Second Chance at Love?

It's round two, and Siggy takes Paul to a local boxing ring to "up" his game. Then, both Paul and Marilyn try out their newly-acquired techniques on blind dates. Will they flame or fizzle?

“To date, you have to get out of your comfort zone. You have to walk a different walk. You have to carry yourself differently.”

Love Gone Wrong
Media outlets recently reported the story of "Mike,” a New York banker who, after being rejected following a first date with a woman named “Lauren,” sent to her a 1,600 word rant-filled email. Could Siggy's tips and tricks have prevented this embarrassing date gone wrong?