When Dating a Friend’s Ex Becomes a Personal Dilemma

Several contributors recount how romantic involvement with a friend’s former partner reshaped their social circles. One writer describes an on-and-off affair with a younger man who later rekindled his relationship with the writer’s ex-husband, resulting in the loss of both the ex-husband and the former best friend. Another recounts a long-term marriage that began after a roommate’s boyfriend became a lover, noting that the original roommate remains a close family friend. A third story details a friend’s betrayal when she and the writer’s ex-husband began a relationship, leading to the dissolution of a close friendship and a broader social group. Finally, one author explains that after dating a former house-mate’s boyfriend, the former house-mate labeled her “the red slag” and severed ties, even though the couple later married and raised a family.

The Guardian

In a small rural setting, respondents note a “five-year moratorium rule” among sisters, cousins and friends: dating an ex is permissible only after five years have elapsed since the breakup. The rule emerged from observed pain when people pursued fresh breakups, aiming to protect friendships. One contributor affirmed that, after divorce, they felt no right to object when a friend asked to date their ex, emphasizing that the relationship had already ended.

The Guardian

The anecdotes reveal recurring themes of regret, jealousy, and social isolation. Writers describe feeling “regret about the friend,” “hurt so much,” and being “instantly rejected” and labeled negatively. Some highlight the difficulty of balancing personal desire with the well-being of children and extended family, noting prolonged periods without contact from former partners. Others point to the necessity of “hard conversations” and honest apologies to mitigate hurt feelings.

The Guardian

• “I felt regret about the friend, and I think of our fling fondly.” — Contributor, personal essay

The Guardian

• “We grew up in a small rural community with an even smaller dating pool.” — Contributor, personal essay

The Guardian

• “My sisters, cousins and friends had a five-year moratorium rule: date any ex, but only after five years had passed since the breakup.” — Contributor, personal essay

The Guardian

• “One of my closest friends FaceTimed me and told me she and my recently ex-husband (who left me for a younger woman) had fallen for each other.” — Contributor, personal essay

The Guardian

• “I was instantly rejected by my friend, who called me “the red slag” and spread the news that I had schemed to steal her boyfriend.” — Contributor, personal essay

The Guardian