Charlie Sheen Updates His Relationship Status With Jon Cryer After ‘Two and a Half Men’

Charlie Sheen has shared insights into his current relationship with former co-star Jon Cryer following their time on ‘Two and a Half Men’.

In a recent interview with PEOPLE, published on April 24, Sheen revealed that he hasn’t spoken to Cryer since the release of the 2025 documentary aka Charlie Sheen, despite Cryer making an appearance alongside others from Sheen’s past.

Sheen mentioned that he has considered reaching out to Cryer but hasn’t acted on it. “I don’t like to bother people,” he explained. He often tells himself he will contact Cryer but has yet to do so.

Nonetheless, Sheen believes that Cryer would be open to reconnecting. He spoke highly of his former co-star, calling him talented and kind. “Jon’s a lovely man and a very talented guy,” Sheen stated.

Sheen also expressed gratitude that Cryer participated in the documentary, along with other cast members and individuals from various aspects of his life. He appreciated that many were willing to share their experiences on camera rather than shy away from revisiting the past.

However, their relationship has faced challenges over the years. Cryer has publicly stated that he and Sheen do not maintain a current relationship. In previous interviews, Cryer noted that tensions escalated after Sheen was dismissed from the sitcom in 2011.

During Sheen’s exit, he publicly criticized Cryer amid a tumultuous period in his life, which further strained their relationship. The show continued for several more seasons without Sheen, introducing new cast members after his departure.

Cryer has since expressed his well-wishes for Sheen and acknowledged hearing positive news regarding his sobriety.

Despite their complicated history, Sheen recently indicated that he harbors no strong anger towards Cryer today. He even joked during a panel discussion that Cryer still appears somewhat distant, although he would like to mend things.

This situation exemplifies a long-standing Hollywood fallout where time has eased tensions, yet the relationship remains unhealed. It seems there is no active conflict now, just a lingering distance. What are your thoughts on this matter? Should former co-stars attempt to reconnect after so many years, or is it best to leave the past behind? Share your opinions in the comments.