For Emmy-winning actress Jean Smart, the journey of moving forward after loss has been marked by profound vulnerability. During a raw and honest appearance on the May 6, 2026, episode of Julia Louis-Dreyfus’ podcast, Wiser Than Me, Smart recounted the “depressing” reality of her first attempt at dating following the death of her husband, Richard Gilliland.
Gilliland passed away in March 2021 after a brief illness, ending a nearly 34-year marriage that Smart described as the cornerstone of her life.
Read more ; ‘Off Vibes A$AP Rocky Spotted Solo in NYC Following Rihanna Argument Rumors
The Emotional Toll of a First Date
Re-entering the dating scene after more than three decades proved to be an overwhelming experience for the Hacks star. Smart described a dinner date where she felt completely disconnected from herself, battling intense self-doubt throughout the evening.
She recalled “standing outside herself” during the meal, constantly critiquing her own conversation and fearing she was being boring or uninteresting. The evening ended with a “friendly little side squeeze” from her date, at which point Smart admitted she had never felt “older or more unattractive.”
Finding Light After Grief
Despite the initial discomfort and the feeling that she would “never hear from this man again,” the actress shared a positive update on her current personal life. Smart revealed that she is now in a relationship with an “extremely lovely man” whom she met at a friend’s gathering.
This new chapter comes as Smart continues to balance a revitalized career with the complexities of widowhood. By sharing her “depressing” first date story, she has sparked a larger conversation about the realities of grief and the courage it takes to seek companionship after a lifetime with one partner.