I have a strange situation. I have a friend who I dated for two and a half years, monogamously. All his relationships have been monogamous. We were each other’s first significant others. I broke up with him, in part because I wanted to experience things with other people. it has been three years since then. He knows now that I’m poly, and that I’m dating someone. I want to talk to him about dating again but I’m not sure how to approach it now that it would not be monogamous. Any tips?

Hey, I was in this exact situation about seven years ago! It turned out well for me, so it is possible. 

My tips is to be direct, but not demanding. Have a conversation with him in a neutral, safe space, and mention that you still care deeply about him, and would be interested in getting back together now that you’ve found a relationship practice that lets you experience things with other people without losing other partners.

Let him know that it’s okay if he isn’t interested - if his feelings for you have faded, or he’s uncomfortable with polyamory - and don’t pressure. Try to keep the conversation simple and casual and don’t drag up all the emotions from when you were dating. Be clear that you’re happy to take things slow, answer his questions about polyamory, and encourage him to explore other partners as well.

Good luck!

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