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1. Your GF is being over-the-top controlling and upset about something that was none of her business in the first place. Who cares who you lost your virginity to, long before you met her? This is one of several reasons I think it's bad policy to share your entire sexual history with your current partner, because if they are insecure or jealous, it can only end up backfiring – and unless you exclusively date virgins, everyone has a sexual history.

   It's a big red flag that your adult GF of four years apparently feels threatened by your 13-yo puppy love sex buddy, even if she's now only a friend of a mutual friend and you're not talking to her yourself. It's kinda scary that your GF is counseling other people professionally in how to manage their relationships, when she can so easily go off the rails in her own relationship.

   Sandy has no obligation to stop being friends with Ruby, just because it makes your GF insecure. And if your GF follows through and cuts Sandy off as a friend, and then demands that YOU also stop being friends with Sandy, because she insists on staying friends with Ruby…well, I guess that choice is up to you.

   If your GF is so insecure and traumatized about disloyal best friends, and so jealous about her BF's short-term lovers from ten years back, why isn't she in counseling herself to try and get herself unstuck? That would seem to be the best solution for everyone involved here.

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