How old is Jackie Oshry? Personal life explored as podcast host and Instagram star welcomes her third child

Jackie Oshry has revealed she is expecting her third child with her husband of six years, Zach Weinreb. Taking to Instagram on Thursday, May 8, the 32-year-old shared a photo of her and Zach, both dressed in white and beige, with their hands joining together to make a small heart gesture on Jackie's growing baby bump.

In the caption, The Toast podcast host wrote:

"Here we grow."

Jackie also attached a Patreon link to the caption, leading subscribers to access her first-trimester vlog and the baby’s gender reveal documentation.

Jackie Oshry's pregnancy announcement was met with congratulatory messages from her elder sister Olivia, younger sisters Claudia and Margo, as well as her friends, fans, and others. Claudia Oshry, media personality and comedian who is also an expectant mother to her first child with husband and Good Guys podcast host Ben Soffer, jokingly commented:

"Did I influence you."

Claudia announced her pregnancy on Instagram in November last year. She shared snippets from when she found out she was going to have a baby, to sharing the news with Ben, and going in for a doctor's checkup. The couple later revealed they were going to have a baby boy, due in spring 2025.

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Jackie Oshry is mother to her two sons — Harry and Charlie

During her appearance on the House Guest Podcast with Kenzie Elizabeth, shared on YouTube in September 2021, Jackie talked about meeting her husband and said:

"We met half at work and half through Hinge."

She added:

"We were both working at iHeartRadio. I started in August, he had already been working there."

Jackie then explained that she was shy and felt awkward around people when she started the new job. She said she wanted to gather courage and make friends. Jackie continued:

"I joined a corporate kickball team where we would go play kickball once a week, and then we would go to drinks after. And I was like, 'okay', like that sounds like fun. So the first week... I started talking to this guy..."

The Toast podcast co-host said the "guy" she started talking to during the first week of their kickball and drinking sessions turned out to be Zach. Jackie recalled she and Zach had a "really good conversation" and described their interactions as "little flirty" and "cute," adding she was "totally thrown off by it."

The podcaster humored she only hoped for making friends, but ended up harboring a crush on Zach. She further added that Zach told her at the end of their conversation that they had matched on the dating app Hinge. He had apparently messaged her on the app but never heard back.

The two began dating around two months after that, on a night when they had dinner with Claudia and her husband Ben to celebrate a project. Jackie and Zach dated for two years before getting engaged. They tied the knot in February 2019.

Jackie Oshry announced her first pregnancy in August 2021. Her son Harry was born the same year. She announced her second pregnancy in March 2023, with a post featuring both her and Zach's fingers, alongside their firstborn Harry's hand on the ultrasound photos.

Jackie Oshry underwent some complications during her second pregnancy, as she discussed on a November 2023 episode of the Healthful Woman podcast. During a routine check-up at 20 weeks, Jackie was informed by the doctors that her cervix was short, which posed risks of a miscarriage or a premature birth of the baby.

Upon consultation with medical professionals, Jackie Oshry got a cerclage procedure done, where her cervix was stitched to keep it closed and prevent early labor. The stitches were removed at 37 weeks, and her son, Charlie, was born healthy at 39 weeks and 2 days.

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Jackie Oshry has maintained her sons' privacy and has not shared their photos on social media.