After the sudden death of her husband, this actress found herself navigating single motherhood at age 70. But through this profound loss, her two sons became her strongest source of support. Their love and presence helped her rebuild her life while embracing a new awareness of her health and well-being.
Jean Smart is best known for her iconic roles in “Designing Women” and “Hacks.” Alongside her successful acting career, she built a life filled with love and family. For nearly 34 years, she was married to actor Richard Gilliland, and together they raised two sons, Connor and Forrest.
Jean Smart and Richard Gilliland pictured holding hands on January 1, 1992 | Source: Getty Images
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.
From Co-Stars to Soulmates
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.
Jean Smart, circa 1980s | Source: Getty Images
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.
Jean Smart and Richard Gilliland at Barker Hangar on January 12, 2020, in Santa Monica, California | Source: Getty Images
Their first child, Connor, was born during her time on “Designing Women.” Reflecting on that time, Jean recalled the night she discovered she was pregnant. Dressed in her character Charlene’s wedding dress, she sat in her dressing room, reflecting on how perfectly timed it all seemed.
Jean Smart and Richard Gilliland attend AMT’s 2017 D.R.E.A.M. Gala on November 11, 2017 | Source: Getty Images
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.
Richard Gilliland and Jean Smart during the Casino Night Fundraiser For Caucus Foundation on August 19, 2006 in Hollywood, California | Source: Getty Images
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.
Jean Smart and Richard Gilliland in Hollywood, California on October 9, 2017 | Source: Getty Images
She took him to multiple clinics, where he was tested for the virus, but no further tests were done. After his passing, Jean reflected on the missed opportunities to identify his condition earlier. She shared how she returned to one of the clinics where Richard had been tested and confronted the staff.
Richard Gilliland on set of “Desperate Housewives” on September 27, 2009 | Source: Getty Images
“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.
Jean Smart and Richard Gilliland at an Emmy Party in 2006 | Source: Getty images
Describing the experience of losing her husband, Jean called it “the worst.” She explained how surreal the loss felt, saying, “You go through this period of thinking, […] ‘This isn’t real.’ You know? ‘This just doesn’t make any sense.'”
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.
Jean Smart at the Academy Museum of Motion Pictures on December 15, 2022, in Los Angeles, California | Source: Getty Images
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.
Jean Smart in Los Angeles, California on September 12, 2022 | Source: Getty Images
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.
Her youngest son, Forrest, was just 12 years old when Richard died. Jean was acutely aware of how his father’s loss affected him. She reflected on the trauma of losing a parent so young, a pain she knew would stay with him for life.
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.
How Her Sons Became Her Support System
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.
For her youngest son, Forrest, support came in a different form. While only a teenager, Forrest’s presence served as a constant reminder of Jean’s purpose. His emotional well-being was one of her biggest priorities after Richard’s passing.
Jean Smart with Forrest and Douglas Gilliland at the star ceremony where she was honored with a star on the Hollywood Walk of Fame on April 25, 2022 | Source: Getty Images
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.
Jean Smart with Forrest and Douglas Gilliland pictured on April 25, 2022 | Source: Getty Images
Meet Connor and Forrest Gilliland
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.
Jean Smart attends the First Annual “Celebrate Starlight! Gala on October 2, 1993 | Source: Getty Images
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.
Forrest Gilliland and Jean Smart at the 28th Screen Actors Guild Awards on February 27, 2022 | Source: Getty Images
While many teenagers feel awkward about their parents’ jobs, Forrest had a particularly unique experience as the son of an Emmy-winning actress. At first, he didn’t care to watch any of his mother’s shows, dismissing them as “weird” because they didn’t align with how he viewed her as “just mom.”
Jean Smart and her son Forrest attend HBO Max’s “Hacks” Season 2 Los Angeles premiere on May 9, 2022 | Source: Getty Images
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.