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Young family watching TV
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Dear Anna,

My ex and I have been separated since our daughter was
9 months old (she’s almost 2 now), and we still keep in contact, of course for our child, but also for non-child-related reasons. By the time I moved out of his house, he was already talking to a new girl, now his girlfriend, who is insecure of our friendship. At 18, he was my first everything, and although he isn’t my only partner after separating, we still have not gone more than five weeks without sleeping together. I’d like to think it’s not planned, but I see a toxic pattern I can’t get out of. He’s opened up and admitted to seeing a great friend in me and knows he can be vulnerable without judgment around me. As for me, I do not see my life by his side anymore. I know too much to trust him again, and yet I have an immense heart for him and his problems. Can we be friends? Is it healthy?
—Stupid And Young

Dear SAY,

You can be friends with your ex, and you probably should. As a product of a very non-amicable divorce (hello, supervised court visitations!), I can tell you it’s much easier on everyone if parents get along. Of course, there’s a distinct difference between a friendly relationship and a friends-with-benefits relationship, and I think for the sake of uncomplicating your life, you should cease the monthly-ish bone sessions.

Plus, let’s be honest, I’m sure his girlfriend is none too thrilled about it and has every right to feel insecure of your “friendship.”

The trick now is to start creating some boundaries for yourself so that you both can cordially and cooperatively parent with and support each other. So. I want you to sit down and really think about what kind of place you want your ex to occupy in your heart and life. What feels good to you in the long run? What would your life look like?

I also want you to think about whether your relationship with him is stifling you in any way—is it interfering with your dating life? Are you offering him a lot of support when you should be using that support for yourself? Are you still, in certain ways, “by his side” when it might better serve you to focus on your heart and healing and all that? It’s possible I’m reading too much into this, but women are often taught to be caretakers for other people, while neglecting our own needs.

Perhaps it’s all fine and you’re simply looking for a little extra resolve to stop falling back on old habits. Your ex is familiar and your first “everything,” and because of your child, it really IS “till death do you part,” so now is your chance to start building the kind of relationship you want with him.

The upside to separation is that you and your ex no longer have expectations of each other (as romantic partners, at least). As a result, you can carve out your own unique space for happiness and trust and honesty.

Your life is as expansive as you want it to be. With a little time and platonic good behavior, I think you can find that sweet spot.

Best of luck, SAY.

Anna Pulley is a RedEye contributor. Got a question of your own? Email redeyedating@gmail.com. Or let her send you overly personal emails here.