Feeling Perplexed

Dear Amy,
I have been dating a guy for about nine months. A while ago he broke up with me because his friends were pressuring him to hate me. But, later the same day he "took it back". I forgave him and we started dating again. I don't know why I forgave him. I guess I thought I loved him. Anyways, he broke up with me again just a few days ago saying that breaking up with me the first time took a chunk out of our relationship that can never be replaced and that he knows his best friend likes me. He told me he still wants to be friends. I know his best friend likes me and had often found myself dreaming not about my boyfriend but his best friend. Should I stay friends with my ex? Should I date his friend?

Dear Perplexed,

Hmm. Sticky.

       So, I some red flags going up here (one of moments when I wish I could ask lots of clarifying questions). It seems “strange” to me that a half a day breakup could take some irreplaceable part of your relationship away. I’m not sure why this strikes me as odd but I think there’s more to the story. And why is the friend coming up in the conversation?
     Ok, so if you and I were sitting across a table, I would suggest that you leave that whole situation alone for a while. You can stay friends with your ex, but I wouldn’t date his best friend anytime soon. Not sure why your ex is suggesting that you do and when faced with uncertainty, I suggest caution. Generally speaking, dating an ex’s best friend is a recipe for all sorts of drama so even if he condones it, I’d still give it some time to see how things work out.
     And why in the heck are his friends wanting your ex to hate you? And on the same note, why in the heck did he take them up on it (even if he took it back)? 
     My advice: stay civil and friendly but avoid any further emotional entanglements with this crowd until you have a better understanding on what they’re all about.

Amy