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Issa Celebration! Jess Hilarious Confirms BIG Life Update On Her 32nd Birthday

Roommates, Jess Hilarious is celebrating 32 years of life today (Feb. 13)! But that’s not the only thing worth hyping up in the comedian’s life. During this morning’s ‘Breakfast Club’ show, Jess Hilarious’ boyfriend, Chris, spilled that they’re expecting a “little bundle of joy.” Yup, you read that right! Jess Hilarious is pregnant with her second child!

Pregnant Jess Hilarious Reveals How Far Along She Is

She confirmed the news after her boyfriend announced the update while wishing her a happy birthday on air.

“Hey baby, it’s your man. I wanted to call and say Happy Birthday, I know this is a special day for you. I can’t wait to see you, I’m so proud of you. I love that you’re standing divine all the time, and you just such an amazing woman. I can’t wait to see you later, and then I’m so excited for our little bundle of joy as well, baby,” Chris said.

Despite seeming unprepared to reveal the pregnancy, Jess smiled and thanked her man for the well wishes.

At first, Charlamagne asked Chris to repeat himself, and the boyfriend did — loud and proud! But when DJ Envy tried to actextrasurprised, Charlamagne seemingly hinted they already knew about the baby bump. He told Envy to cut the theatrics, and then they both congratulated their co-host.

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Jess shared that she’s three months (13 weeks to be exact) after Charla asked. He then suggested to Chris, who was still on-air, that an “engagement ring” would make the perfect Valentine’s Day gift.

Well, we can’t say for sure whether he plans to take the advice, but he seemed to consider it with a “Oh yeah, don’t worry.”

As mentioned, Jess is already a mommy to 11-year-old son, Ashton, from a previous relationship.

See the sweet announcement below.

Not much is known about Jess and Chris’ relationship, but it’s clear he’s tight with Ashton as the lil’ family appeared to spend the Thanksgiving holiday together.

Jess’ Pregnancy Comes Amid Her New Hosting Gig

Just a few weeks ago, Jess was celebrating yet another life update: a new job! After several sessions co-hosting ‘The Breakfast Club’ with DJ Envy and Charlamagne last year, Jess Hilarious accepted the permanent co-host position in January.

The show had been operating on a guest host system since Angela Yee departed in December 2022 for her nationally syndicated radio show on iHeart Radio.

Jess’s acceptance of the position didn’t come without controversy, though. In December, she went viral after announcing she had been offered the position. However, for weeks after, neither Charlamagne nor DJ Envy validated her announcement. Instead, TBC vets publicly discussed being unclear on the iHeart’s process of selecting a new host.

Meanwhile, Jess stirred up rumors of an internal beef with the hosts after she blasted them for comparing Mary J. Blige and SZA on-air.

All that quickly went away, though, after Jess Hilarious released her second official host announcement. And yes, this time, DJ Envy and Charlamagne showered her with support online, even appearing in her announcement video.

Happy Birthday, and a HUGE congrats to Jess with the Mess!

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Cassandra Santiago

Cassandra Santiago is a multimedia journalist, editor, and editorial strategist with over a decade of experience shaping conversations across arts, entertainment, culture, and global news. A graduate of the University of Iowa, she has built a cross-platform career spanning newspapers, magazines, radio, and digital media. She joined The Shade Room five years ago and currently serves as a Senior Editor, where she leads editorial direction, oversees exclusive coverage, and trains and edits a team of writers. Cassandra has played a key role in developing high-impact content and editorial strategies for an audience of more than 30 million, contributing to platform growth, engagement, and monetization across multiple channels. In addition to her leadership role, she remains a daily contributor, with her articles generating more than 41 million views since 2023. Beyond The Shade Room, Cassandra offers freelance social media strategy services, speaks on the influence and impact of Black media at public panels, and owns Did It For You, an event design company in the DC, Maryland, and Virginia area. She is Poynter Institute–certified and was named to the DMV’s 35 Under 35 list in 2024.

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