Matthew Perry almost asked Lizzy Caplan to marry him — ‘never’ spoke again after ‘harsh’ email

Matthew Perry, in his memoir, revealed that he never spoke to Lizzy Caplan again after their breakup in 2012. They met when Caplan was 23 and Perry was 36, and despite their age difference, they engaged in a two-year long "friends with benefits" relationship. They kept their relationship private and strictly followed the rules without any emotional attachment or discussions about their personal lives.

However, their relationship eventually turned into love and Perry confessed his feelings to Caplan, who didn't disagree. Both of them were committed to their work and had a fear of abandonment. Perry even considered proposing but backed out at the last minute. He commissioned a painting of them during Christmas but missed the opportunity to propose.

In May 2016, Caplan got married and declined Perry's invitation to see his play in London due to her busy schedule. She later informed Perry about her marriage and her desire to cut off all ties with him. Since then, they have had no contact, and Perry wishes her nothing but the best.