That stability was shattered in 2021 when Gilliland died suddenly at the age of 71. His unexpected passing left Jean to confront new responsibilities and hard decisions as she grieved. Her sons’ support became a lifeline as they adjusted to their new reality as a family of three.

Jean and Richard’s love story started on the set of “Designing Women” in 1986. At the time, Richard was playing J.D. Shackelford, a love interest for another character. But behind the cameras, his heart was set on Jean.

The connection was undeniable, and the two quickly began a relationship. Their love blossomed, and they married in June 1987. Over the years, their partnership grew stronger as they expanded their family.

Later, Jean and Richard decided to expand their family more through adoption. Their second son, Forrest, was adopted from China after a long and emotional process. “I just cried one day,” she shared, noting that her emotional plea ultimately led to Richard agreeing to the adoption.

They continued to support each other through career highs and lows while raising their two boys. Their story stood as an example of enduring love in Hollywood — until everything changed.

A Loss No One Saw Coming

On March 18, 2021, Jean’s life changed forever when her husband died after a brief illness. His death was sudden and unexpected, catching the family completely off guard. Jean later revealed that they initially believed he might have COVID-19 due to his symptoms.

“I said, ‘If I brought my 71-year-old husband in here, who was complaining of pain when you take deep breaths, what would you do for him?’” she recalled.

The response she received was that an EKG would have been done — something that never happened when Richard was alive. Her frustration and grief were palpable.

It wasn’t just the loss of her partner — it was the loss of a future they had built together. As Jean confronted the reality of her loss, she had to face an even bigger challenge — raising her two sons alone.

Raising Two Sons Without Her Partner

When Richard passed away, Jean was left to confront a reality she wasn’t prepared for — single motherhood. After years of shared parenting, she was suddenly the sole caregiver for their two sons, Connor and Forrest. It was a shift that came with immense emotional and practical challenges.

One of her biggest realizations was the importance of caring for her health. With no partner to lean on, she knew that her well-being was directly tied to her ability to care for her children. “If something happens to me, what happens to my kids?” she reflected. This new awareness prompted her to make her health a priority.

In early 2023, she underwent a heart procedure, and later that summer, she had an appendectomy. Jean acknowledged that if she hadn’t been a single mother, she might have delayed seeking treatment.

But while the responsibilities of single parenthood were overwhelming at times, Jean did not face them entirely alone. Her sons, especially her eldest, Connor, stepped in to offer the support she needed.

After Richard’s passing, Jean’s eldest son, Connor, moved back home to help with the household and family responsibilities. Having his steady presence in the home gave Jean a sense of comfort and stability.

She admitted that she doesn’t know how single working mothers do it without support. “[Connor’s] been helping me a lot since we lost his dad, and so it’s been very nice to have him around,” she said.

She was acutely aware of how the loss of a father could affect a child, especially at such a formative age. Knowing this, she remained deeply involved in his daily life, ensuring he felt supported despite. For the 73-year-old Jean Smart, knowing that her sons are by her side makes the burden of single parenthood a little lighter.

Connor Gilliland grew up surrounded by lights, cameras, and production crews. His earliest memories are of the “Designing Women” set, where he would sit in the director’s chair and mimic the production process. Even as a child, he had a “serious” nature, contrasting the lighthearted energy of the set.

Forrest Gilliland’s journey is equally unique. When they adopted him, Jean was in her 50s. She often recalls the emotional process of his adoption and how they were “besotted” with him from the start.

But that changed when his friends started watching Jean’s hit show “Hacks.” His friends’ interest sparked his own curiosity, and eventually, he sat down to watch the first season. He finished it just in time for the premiere of the second season, a moment his mother recalls with a mix of pride and humor.