Can I Pursue a Relationship With My Ex-Girlfriend's Best Friend?

Dear eNotAlone: I have recently found myself in an odd situation. It started last week when I ran into my ex-girlfriend's best friend, who I hadn't seen in years. Her name is Cara and we got along well throughout our conversation. We kept in touch, and this past weekend we somehow ended up kissing. I'm in a confused state, because while the kiss felt very nice, I'm not interested in getting into a new relationship anytime soon, let alone one with a friend of my ex. I don't know if it's because of nostalgia for my past relationship or if there are feelings between us. I also worry about how my ex would feel about it. Should I take things further, let Cara know that I want to pursue something, or stay away from her altogether?

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This is definitely a tricky situation. On one hand, it can be easy to look back on your past relationships and connect to them in ways you may not have anticipated. On the other hand, it is certainly understandable to want to keep your relationship with Cara separate from your past one. With that being said, it is important to acknowledge both your own feelings, as well as Cara's. It is important to consider the impact any decision may have on your ex and think carefully before acting upon a conclusion.

I would suggest honestly deliberating with yourself beforehand. Ask yourself if you are truly ready to embark on a new relationship, and if Cara is someone you could possibly see yourself having a serious relationship with. Have you tapped out all of your feelings related to your past relationship to be sure that any romantic feelings between you and Cara could exist without the effects of nostalgia? Do you trust that Cara has the same intentions as you? If the answer to these questions is yes, then I would suggest continuing to spend time together with open communication to determine if you two could be compatible.

It is also important to keep your ex in consideration for this type of decision, as any action you take could potentially strain your relationship and be damaging if handled carelessly. Your feelings for your ex should remain void during this time and any apprehensions concerning your ex should be communicated in a clear manner to Cara. If you and Cara realistically see a future together, then deciding what steps to take may depend on the nature of your friendship with your ex, so it can be helpful to include them in the loop as well.

If, after honestly assessing the situation, you and Cara decide to pursue a relationship together, it is important to be vigilant in the way you communicate and the decisions you make. Make sure that you enter into a relationship in a way that honors both yours, Cara's, and your ex's feelings, as well as being mindful of the awkward dynamic that could be caused by such a situation. The key is being honest, respectful and most of all, making sure neither you nor Cara force yourself into a place where you are not comfortable.