In between building a historic career in media, Barbara Walters married for a second time in 1963 to Lee Gruber, a theater producer. The marriage lasted for 13 years according to The Things, before the couple divorced. In an interview with ABC News she revealed, "I don't think that I was very good at marriage. It may be that my career was just too important. It may have been that I was a difficult person to be married to, and I just seem to be better alone. I'm not lonely, I'm alone." 

Candidly honest about her struggles with infertility, Walters and Gruber adopted daughter Jackie, named after her sister Jacqueline. Preferring a more quiet life, Jackie is rarely photographed, and mother and daughter had a notoriously rocky ride during her teenage years (via The Things). 

In a 2014 interview with Piers Morgan, Walters expressed her greatest life regret, sharing, "[I] regret not having more children." But Walters also noted to ABC News, the same year that, "I was so busy with a career. It's the age-old problem." Adding, "And, you know, on your deathbed, are you going to say, 'I wish I spent more time in the office?' No. You'll say, 'I wish I spent more time with my family,' and I do feel that way. I wish I had spent more time with my Jackie."