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Sherri Shepherd is a divorced woman now and she’s happy about it. Maybe not so happy about the child support she’s been ordered to pay her now ex-husband Lamar Sally, for the baby they had via surrogate, but happy nonetheless. But Sally and other ex-husband might not be the worst guys she’s ever dated. Shepherd also dated a guy in jail. She says he wasn’t in jail at first, but went to jail while they were dating. And it wasn’t some quickie relationship that went bad. Shepherd dated the guy four years before he went to jail and for a year afterward. 

“Yes, I dated somebody in prison,” Shepherd confesses. “I dated him for about a  year [after he went to jail.]He went to get a pizza and apparently he was burning up buildings. I was living in California with my parents and we saw him on TV. They did and sting and they had him on the ground and everything. I turned the TV off before my father saw him because I didn’t want to hear his mouth. I thought he was cheating. I followed him once but he went too far so I went back home. I dated him about 3-4 years before he went to jail.”

Shepherd’s confession comes as the result of a listener’s Hot Button question. A concerned aunt says her niece, who is in college, is in love with a man who is in jail. He writes her poetry and is getting his degree in jail. But Shepherd says that her future might include planning an escape.

“This is what happens when you date a prisoner,” Shepherd says. “A lot o collect phone calls that you’re paying for, a lot of money you’re putting on folks’ books. Yes, they send you a lot of poetry with a lot of words  you can’t pronounce, then they want to become Muslim in prison. And then I even went one Christmas on a Motown to see him and your butt hurts from sitting in a plastic chair for eight hours and you can only eat a candy bar from the vending machine, then you take a picture in front of mural with whales on it. You can’t do nothing because you’re not married and the guards are looking at you like you’re nothing and then the guards are looking at you like why didn’t you bring anything smuggled under your breast. It is not a good life. ”

Although her ex  had a 14-year-sentence, Shepherd says she was willing to marry him despite it. They were preparing for the jailhouse wedding, until Shepherd received a Valentine’s Day card – addressed to another woman.

Sherri Shepherd: ‘Yes, I’ve Dated A Man In Jail’  was originally published on

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