Laura Ingraham, Age 57 – Single

Even though she is a mother of three, Laura Ingraham has never actually been married, that doesn’t mean, however, that she hasn’t come close. She’s currently a single working mother to her three adoptive children, that lives a high-profile life, being the host of The Ingraham Angle.

She’s publicly dated men like her co-worker, Keith Olbermann, and Dinesh D’Souza, but unfortunately, none of these relationships worked out. The closest she ever got to getting married was when she got engaged to James V Reyes, with whom they broke off their engagement shortly after they announced it, while she was diagnosed with cancer.