Jess Hilarious has built a career on telling the truth in a way that makes people laugh and feel seen, from the Baltimore open mic scene to Wild 'N Out, starring on Rel, her hit podcast Carefully Reckless, and now co-hosting The Breakfast Club. But in this conversation, we go somewhere most people have never heard her go: what it really took to become the mother and co-parent she is today.

Jess got pregnant at 19, raised in a strict church household, terrified to tell her parents she even had a boyfriend. She opens up about the first six months after her son Ashton was born, when she didn't want to be a mom at all, and the breakdown on her knees in her mother's house that ended with her baby smirking up at her from the crib. That was the moment everything changed.

We also walk through the hard road with her son's father, Jerome. The cheating, the other girl at Ashton's first birthday party, and the public comment that revealed he had a second child on the way. Instead of staying at war, Jess chose to understand the trauma behind his behavior, and the two of them took actual co-parenting vows: for better or for worse, till death do we parent.

As a father of four boys, I know how many men in our community are navigating co-parenting right now, and this episode is packed with hard-won wisdom on boundaries, accountability, and putting your kids first. Jess's new book, Til Death Do We Parent, brings her trademark humor and honesty to all of it, and this conversation is the perfect introduction.

Timeline Summary

[1:01] Larry welcomes comedian, actress, and Breakfast Club co-host Jess Hilarious to the show

[1:48] Jess opens up about not wanting to be a mom for the first six months after her son was born

[3:15] Telling Jerome she was pregnant at 19 and his unexpectedly joyful reaction

[4:25] A charge on her record, no job offers, and moving back in with her mom after Ashton arrived

[4:52] The breakdown in her mom's house: "why would you pick me to be your mother?"

[7:17] Telling her parents at 8 PM: her dad's ten-second breathing technique and her mom's prayer

[15:02] The funeral story at age eight that proved Jess was born funny

[17:43] Martin Lawrence's brother calls and Jess fakes ten years of stand-up experience

[18:41] Opening for Martin Lawrence in front of 13,000 people in Baltimore after five open mics

[25:05] Rome brings another girl to Ashton's first birthday party

[26:57] Leaving a good man for one more chance, then learning about Rome's second child from a public comment

[31:14] Understanding Rome's trauma: losing his mother at ten and finding her himself

[33:32] The co-parenting vows: "I take you, Jerome James, to be my lawfully wedded co-parent"

[35:22] Dating selfishly and taking accountability for the men she brought around Ashton

[38:15] The 1 AM phone call that made her husband draw the line on boundaries

[42:58] Larry shares meeting his biological father by chance in a St. Louis Starbucks at age 30

Five Key Takeaways

Treat co-parenting like a vow you can't walk away from, because your child is watching how you show up for better or for worse.
Your kids absorb every ounce of tension between you and your ex, and defiance at school is often a reflection of the energy they're consuming at home.
Understanding the trauma behind your ex's behavior won't excuse it, but it can free you from resentment and make a real friendship possible.
When you have kids, you date as a package, so anyone who isn't building a bond with your child isn't actually good for you either.
Boundaries protect every relationship you have, and putting "friendship hours" around your co-parent isn't disrespect, it's what keeps your marriage and your co-parenting healthy.

Links & Resources

Til Death Do We Parent by Jess Hilarious: https://www.amazon.com/Til-Death-Do-We-Parent/dp/1668059355
Jess's website — https://jesshilariousofficial.com
Follow Jess on Instagram — @jesshilarious_official
Follow Jess on Twitter and Snapchat — @jess_hilarious
Jess Hilarious Official on Facebook
Episode resources — https://thedadedge.com/1490
Questions for the Car free download — https://thedadedge.com/questions
The Dad Edge Alliance — http://thedadedge.com/join

Closing

There's a moment in this episode where Jess describes falling to her knees, asking her infant son why he chose her as his mother, and looking up to see him smirking at her from the crib as if to say "I'm here, so put on your big girl panties." That's the kind of raw honesty that changes how you see your own parenting story. If you're navigating co-parenting, boundaries, or just the weight of feeling unready, share this one with a brother who needs it. Go out and live legendary.