Jean Smart has opened up about the emotional difficulty of re-entering the dating world following the death of her husband, describing her first post-loss date as deeply unsettling and “depressing.”

The Emmy-winning actress lost her husband Richard Gilliland in March 2021 after a brief illness. The couple had been married for nearly 34 years and shared two children.

Speaking on the May 6 episode of Julia Louis-Dreyfus’ podcast Wiser Than Me, Smart revealed that she is now in a relationship with what she described as an “extremely lovely man,” whom she met at a friend’s gathering. 

However, she admitted that the process of dating again after her husband’s death was emotionally overwhelming.

Recalling her first date in more than three decades, Smart said, “We went out to dinner and I was just a wreck, an absolute wreck.”

She added, “I remember standing outside myself, watching myself in this restaurant, just going, ‘Oh God, you didn’t just say that. Oh, could you be more boring? Could you be less interesting? Oh my God. Oh my God.’ All night.”

At the end of the evening, Smart said the man gave her a “friendly little side squeeze,” prompting her to disclose that it was her first date since becoming widowed.

“I have never felt older or more unattractive than I did in that moment,” she said. “I went home thinking, ‘I will never hear from this man again.’ It was just so depressing.”

Despite the initial discomfort, Smart ultimately found connection again, marking a new chapter in her personal life while reflecting honestly on grief and vulnerability.