Can I date my friend’s ex?


John and Sara are both great people who have been my friends for a long time, though I am closer to her. We are all in our early 30s. Sara is someone I met in my 20s and John and I grew up together. They met through me and dated for a few years almost a decade ago. I was thrilled to have two great friends fall in love but they had a messy breakup and haven't spoken in years.

Fast forward to now. Sara is still pretty sensitive about the relationship but has since moved on and is with a wonderful man she will spend the rest of her life with. John and I both find ourselves single and have realized we have a mutual attraction; we recently shared a passionate kiss that surprised both of us.

We've always been friends but perhaps there is something more. He has all the qualities I am looking for in a life partner. John invited me to spend a weekend away with him to try to find out if there could be more to our friendship that we've been missing all these years. I would love to explore this but if we did end up in a relationship, I know Sara would feel betrayed and it would definitely not be OK with her. But maybe over time she could come to accept it. Her current relationship is amazing but John will always hold a strong place in her heart.

Should I keep my distance from John and keep things on the casual friend level like they've always been? Or keep an open mind, explore things with him to see if there's even some possibility for more first, before worrying about the rest and Sara?

– Once a friend's boyfriend always a friend's boyfriend?, Boston

My first piece of advice? Don't take a weekend trip with John to figure this out. Weekends away don't solve anything. You need to ask John -- while you're here in the real world -- whether he wants to pursue this or whether he's just scratching an itch. Spend an evening or two as friends and see how it feels. On an average Wednesday, are you thinking about kissing him? And on that average Wednesday, what does he think of you?

If both of you do want to try dating, you've got three options.

1. Pursue this, come clean to Sara, risk losing her.

2. Don't pursue this, resent her.

3. Tell Sara that you kissed John and that you're freaking out. Ask her if it's possible to date him without losing her. Let her know how conflicted you are. (Crying wouldn't hurt.)

I'd go for 3. It's very possible that Sara will say, "Stay away from him," but it's more likely that she'll look at her single friend and say, "Let's try to deal with this." She'll be angry, but at least she'll know that you aren't keeping any secrets.

We've all been the Sara, the person who can't quite get over a John from long ago. The idea of a close friend dating any of my Johns is pretty overwhelming. But my love for my Saras, and my desire for them to be happy, trumps my resentment toward any of my Johns.

Talk to John about his intentions -- here in the real world, not on a weekend away. If after some normal friend outings you both want to take the next baby step, sit down with Sara and ask for guidance.

Readers? Should she stay away from John? What are the rules here? What about this weekend away? How is Sara going to react? Discuss.

– Meredith