Would You Date Someone Who Sees Their Ex Every Month?

A listener writes in with a dating dilemma that sounds familiar but carries more weight than it first appears: a guy reveals on the fourth date that he is still friends with his ex—a ten-year relationship that ended a year ago, initiated by her. They see each other once a month. He insists he has no romantic feelings left, but describes her as "an important person in his life." The question is whether this is a red flag or a deal breaker.

Jordana and Jared agree that the answer depends heavily on nuance, but the details here tilt toward trouble. A ten-year relationship that ended only a year ago is not a clean break. The fact that she ended it raises the question of whether he is holding on because he hasn't fully moved on or built a life as an individual. Seeing someone once a month is a significant, scheduled commitment—more than most people maintain with close friends they aren't romantically involved with. Jared points out that he himself doesn't see his co-host that often. The fact that he brings it up on the fourth date suggests he knows it could be an issue and is trying to get ahead of it, which is fair, but it also means he is aware the arrangement is unusual.