Howard Stern Finally Reveals The Truth About His Relationship With His Much Younger Wife's Family

Summary

• Howard Stern finally opens up about his relationship with Beth's brother Doug and her parents on his radio show.
• Despite being intimidated by his athletic brother-in-law Doug, Stern gets along well with him.
• Stern struggles to connect with Beth's father but tries to impress him by talking about sports.

One of the keys to Howard Stern's incredible financial success in the radio and entertainment business is his willingness to be open and brutally honest. But while Stern has frequently exposed some of the dark marks of his story, including his physical altercation with a famous comedian's boyfriend, he has been rather silent about his relationships. This includes the real reason for his divorce from his first wife, Alison Berns, and the inner workings of his second wife's family.

While Howard Stern does speak a bit about his relationship with his wife, Beth, fans know next to nothing about how he actually gets along with her family. This wouldn't be interesting if it weren't for Stern's extremely particular personality and the fact that he's 18 years older than Beth. Meaning that her siblings could be his children and her parents, his contemporaries. On Stern's April 3rd, 2024 show, he finally revealed the truth about his relationship with Beth's brother Doug Ostrosky, and their parents. This article will reveal what Stern said about Doug and his family, as well as what he said about his relationship with Beth's elderly parents.

Inside Howard Stern's Relationship With His Wife Beth's Brothers

Howard Stern and Beth Stern have been married since 2008 after dating for several years following his divorce from his first wife and the mother of his three daughters, Alison Berns. While much of Beth's personal life has been revealed on her husband's acclaimed SiriusXM radio show, next to nothing was known about her two brothers or her parents. But this changed when Stern not only addressed his relationship with Beth's siblings on his show but actually hosted one of them for a semi-interview.

• Beth Stern (Nee' Ostrosky) has two brothers, Doug and Dave Ostrosky

Leading up to Stern's April 3rd, 2024 radio show, he revealed that they were hosting Beth's brother, Doug, and his family for a few days. This wasn't the first time Doug, is wife, Amy, and his two children (Luke and Ainsley) visited his sister and brother-in-law's house. But it was the visit that received the most exposure on Stern's radio show. And it all started with Stern explaining that he's intimidated by his brother-in-law, Doug, and his physical abilities.

"We had dinner with my brother-in-law and sister-in-law and the kids, it was nice to see them and we had a good time. They're going to be here for a couple of days," Stern said to his co-host Robin Quivers on the air.

"My brother-in-law was outback tossing a football with his son. And I went inside and hid. He was a division one football player at Penn State."

Doug then claimed that he would've loved to see Stern throw a football as he would have made fun of him for his lack of skill.

• Doug Ostrosky is the Director of Retial and CPG Technology Strategy at Microsoft, according to his LinkedIn
• Doug Ostrosky and his family live on Bainbridge Island, Washington

While Stern doesn't exactly impress Doug athletically, they actually get along quite well. They bond over them nothing learning how to play the guitar and Stern's radio show. Doug is reportedly a huge fan of The Stern Show and some of the edgier bits that his staffers Richard Christy and Sal Governale contribute. Doug's knowledge of The Stern Show lore was evident to fans listening to his interview, proving that he is not an average listener of the show but, in fact, a superfan. Whether or not Doug Ostrosky was a fan of The Howard Stern Show before his sister married the radio legend is unknown at the time of this writing.

Even still, Stern is unhappy he isn't as athletic as his wife's brothers. But Beth claimed that she wanted to teach him how to play football despite the fact that he's 70 years old.

"She's going to teach me football," Stern said. "How emasculating."

"How can you be my brother-in-law and look me in the face?"

Doug then responded, "I can't."

Stern then claimed that he didn't have any male role models growing up to teach him how to play sports. Doug then claimed that his brother, Dave, was his older male role model but that turned how terribly as he claimed Dave is extremely competitive and aggressive.

• Dave Ostrosky was a Division One basketball player

"This family, I can't be around them, they're too successful."

Doug claimed that he too would help Stern learn how to shoot a basketball. In fact his son Luke would also help. Doug also claimed he would teach Stern and his staffers how to properly bet on various games, primarily football.

Inside Howard Stern's Relationship With His Wife Beth's Mom And Dad

Howard Stern claims that he struggles to speak to Beth's father, Robert Ostrosky. While Robert was a renowned dentist, he is also extremely athletic and into sports. Therefore, Stern admitted that he tries to memorize a few "masculine" facts before visiting with Beth's dad. During Stern's April 3rd, 2024 show with Beth's brother, Doug, fans learned that Robert Ostrosky is hard of hearing and therefore doesn't always catch what Stern said to him.

"I'll say to him -- 'what do you think about, you know' -- I'll name some player that I read about," Stern said. "He loves it."

"He does love that," Doug Ostrosky said about his father. "Just ask him something [about sports]."

Beth then said that her parents were on their way over to visit which didn't exactly have her excited. Stern tried to ease her into the visit, claiming that they'd have a good time. Stern also claimed that Beth's father also likes to talk about sex and the women he's been with in front of Stern.

"My father-in-law is talking about all the women he's banged and his wife is sitting right there. And I'm like, 'Dude, maybe we should take this in another room, this is really masculine talk.'"

All in all, Stern gets along quite well with his brothers-in-law and his father and mother-in-law despite the age gaps and the differences in interests and personalities.