Gavin’s memoir recounts a conversation with his sister Hilary, who criticized his tendency to let women influence his decisions. She highlighted his embarrassing behavior at a red carpet event, which she attributed to his then-wife, Kimberly Guilfoyle, and Ann Getty.
Hilary remarked on Gavin’s lack of self-awareness, saying, “If I had been there, I would have told you: ‘Get your a– off the floor. You’re the mayor of San Francisco. That is not a good look.'”
Gavin also shared his sister’s view of Guilfoyle, describing her as “smart, quite smart, but not [her] type of gal” because her desire for attention and affection could not be satisfied.
Hilary added that Guilfoyle’s style was excessive, noting, “She was never not put together, but understatement was not one of her attributes. She needed to command a room. She needed to own a room. All eyes on her.”
Gavin and Guilfoyle, described as a MAGA disciple, were married in December 2001, an event during which Tessa “put on a good smile.”
Gavin’s mother believed that his marriage to Kimberly “would not last,” though she chose to conceal these feelings from him.
Guilfoyle was absent when Tessa passed away through doctor-assisted suicide. She had visited the day before, only to be reprimanded by Tessa for issues in the marriage, leaving Guilfoyle in tears. It seemed that Tessa had finally found a voice.
Hilary observed a similar dynamic in their relationship, noting, “I saw a lot of adoration from her to you, Gavin. But less from you to her.”
Tessa was concerned that Gavin had brought passivity into the relationship. Gavin admitted in his memoir, “I gave only a little of myself to Kimberly. Instead of regretting this, I kept wishing I could have given a lot more to my dying mother… The distance between Kimberly and me became a breach, and the breach widened into a chasm that could not be repaired.”
Gavin concluded by stating that when they decided to end their four-year marriage, it was done as amicably as possible.
