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Ask Olive: Should I Stay or Go?

Dear Olive,

I’ve been a serial dater throughout my early 20s and have put enormous effort into meeting lots of people in the hopes that I might begin a healthy and supportive long-term relationship. Not once but twice in a row, I found myself at the beginning of what seemed to be very promising relationships with men I cared about very deeply and felt really compatible with. Although I didn’t seek out partners with this quality specifically, they were both recently single after being in long-term relationships. After dating each of these men for a few months, they both decided they needed more time to be on their own and broke up with me.

I’ve recently met someone new (this time IRL, at a BBQ, through mutual friends, instead of through dating apps — who knew such a thing was still possible?). He is just a few months out of a four-year relationship, and we have spoken frankly about the fact that this is an unhealthy pattern I have found myself in before, which I rather unaffectionately refer to as the Danger Zone. He seems confident that taking things slow and giving it time will be for the best. Part of me agrees with that, but part of me wants to run screaming for the hills.

Everyone needs different things in order to heal and move on from their past, and everyone needs a different amount of time in order to do that. Is there a cut-off for how soon is too soon? Should I shut myself off from possible happiness because a different person in a past situation hurt me? They say that doing the same thing over again and expecting different results is the definition of insanity. Please help me from going insane.

Yours in indecision,

Should I Stay or Should I Go


Dear Should I Stay or Go,
— Olive

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