In the 1960s, Simon was briefly engaged to William Donaldson (who jilted fiancée Sarah Miles for her).
Donaldson described her as "the answer to any sane man's prayers; funny, quick, erotic, extravagantly talented."

Simon married fellow singer-songwriter James Taylor on November 3, 1972.
They had two children, Sarah "Sally" Maria Taylor (born January 7, 1974) and Benjamin "Ben" Simon Taylor (born January 22, 1977), both of whom are musicians and political activists.
Simon and Taylor divorced in 1983.

In June 2004, Simon said that she no longer speaks to her ex-husband. "
I would say our relationship is non-existent.
It's not the way I want it."

She was engaged to musician Russ Kunkel, from 1985 to 1986.

Simon married James Hart, a writer, poet and businessman, on December 23, 1987.
The couple divorced in 2007.

Simon underwent a mastectomy, chemotherapy and reconstructive surgery for breast cancer during 1997 and 1998.
There had been a lump in her breast for several years, but her doctors had advised against surgery.
Simon later recounted: "Then one doctor said, 'You know what, I'd rather see it in a jar than in your breast.'"
She also said that she felt "a little angry with myself" that she did not insist on taking it out sooner.
Simon's surgery came at the same time as the death of her long-time friend Linda McCartney, who had also struggled with breast cancer.
Simon described McCartney's death as having emotionally "crushed" her.
Furthermore, Simon has been suffering from osteopenia since at least the age of 61, which has resulted in her avoidance of high-heeled shoes in order to escape discomfort.

In an interview published on May 1, 2008, with the Bay Area Reporter, an LGBT news service, Simon was asked about the possibility of a performance in the True Colors Tour.
She responded, "The part that I could be involved in is the gay and lesbian part.
The part that would be hard for me is to commit to a tour, because I'm not very comfortable being onstage.
But the part that would be easiest for me would be singing on behalf of all of us.
I don't consider myself to be not gay... I've enlarged all of my possibilities.
I have a lot of extremely personal stories to tell about that, but we won't go into that right now.
Let's just say that it just depends upon who I'm with."

Simon has been close friends with James Taylor's younger brother Livingston Taylor for over 40 years.
Livingston said, "I love Carly and Carly loves me.
She's a ferocious advocate and supporter of my music."
They have worked as a musical duo for some songs such as "Best of Friends", released in Livingston's 2006 album There You Are Again, and others earlier in their careers.

In May 2010, Simon revealed she had been one of the several celebrities who fell victim to financial advisor Kenneth I. Starr, whose Ponzi scheme lured her into "investing" millions of dollars with him, which she lost.

In 2008, Simon was reportedly dating Richard Koehler, a surgeon specializing in minimally invasive laparoscopy.
Koehler, who is ten years younger than Simon, was said to have been dating her as early as 2006.
In 2015 the two were reported living together in Martha's Vineyard.
In the 1960s, Simon was briefly engaged to William Donaldson (who jilted fiancée Sarah Miles for her). Donaldson described her as "the answer to any sane man's prayers; funny, quick, erotic, extravagantly talented." 
Simon married fellow singer-songwriter James Taylor on November 3, 1972. They had two children, Sarah "Sally" Maria Taylor (born January 7, 1974) and Benjamin "Ben" Simon Taylor (born January 22, 1977), both of whom are musicians and political activists. Simon and Taylor divorced in 1983.
In June 2004, Simon said that she no longer speaks to her ex-husband. "I would say our relationship is non-existent. It's not the way I want it."
She was engaged to musician Russ Kunkel, from 1985 to 1986.
Simon married James Hart, a writer, poet and businessman, on December 23, 1987. The couple divorced in 2007.
Simon underwent a mastectomy, chemotherapy and reconstructive surgery for breast cancer during 1997 and 1998. There had been a lump in her breast for several years, but her doctors had advised against surgery. Simon later recounted: "Then one doctor said, 'You know what, I'd rather see it in a jar than in your breast.'" She also said that she felt "a little angry with myself" that she did not insist on taking it out sooner. Simon's surgery came at the same time as the death of her long-time friend Linda McCartney, who had also struggled with breast cancer. Simon described McCartney's death as having emotionally "crushed" her. Furthermore, Simon has been suffering from osteopenia since at least the age of 61, which has resulted in her avoidance of high-heeled shoes in order to escape discomfort.
In an interview published on May 1, 2008, with the Bay Area Reporter, an LGBT news service, Simon was asked about the possibility of a performance in the True Colors Tour. She responded, "The part that I could be involved in is the gay and lesbian part. The part that would be hard for me is to commit to a tour, because I'm not very comfortable being onstage. But the part that would be easiest for me would be singing on behalf of all of us. I don't consider myself to be not gay... I've enlarged all of my possibilities. I have a lot of extremely personal stories to tell about that, but we won't go into that right now. Let's just say that it just depends upon who I'm with."
Simon has been close friends with James Taylor's younger brother Livingston Taylor for over 40 years. Livingston said, "I love Carly and Carly loves me. She's a ferocious advocate and supporter of my music." They have worked as a musical duo for some songs such as "Best of Friends", released in Livingston's 2006 album There You Are Again, and others earlier in their careers.
In May 2010, Simon revealed she had been one of the several celebrities who fell victim to financial advisor Kenneth I. Starr, whose Ponzi scheme lured her into "investing" millions of dollars with him, which she lost.
In 2008, Simon was reportedly dating Richard Koehler, a surgeon specializing in minimally invasive laparoscopy. Koehler, who is ten years younger than Simon, was said to have been dating her as early as 2006. In 2015 the two were reported living together in Martha's Vineyard.
Carly Simon