I recently spoke to Jeremy Glass, a writer for Thrillist who wanted to figure out how to go about tastefully dating a friend’s ex.

Jeremy incorporated my insights into a super cute and useful piece – “How to Tastefully Date your Friend’s Ex” (3/22/16)

You can read Jeremy’s piece about dating a friend’s ex here

…and here’s our conversation in full (below) – what do you think?

JG/Thrillist: Is it OK to date your friend’s ex?

DrCT: When thinking about whether or not it’s ok to date your friend’s ex, like everything else social in life, it depends. Each situation is different, and people may feel differently about the possibility depending on the players in the scenario – in other words, it might be ok for one ex but not for the next. The thing to remember is to be open about your feelings. Though you always run the risk of hurting others, no good ever comes from keeping secrets in these types of situations. It’s also important to remember the evolving power of social norms. Your friend may be ok with what’s happening at one point, but their feelings may change. And so may yours! Hope for the best, but prepare for tumultuousness.


JG/Thrillist: Is it usually a real connection or just a forbidden fruit situation?

DrCT: This also depends. People often idealize things they only see in “highlight reel” form. Your friend’s partner may seem awesome on a Saturday night when that’s all you see of them, but a true connection (regardless of how you met someone) is always tougher to find. The best thing is to be honest with yourself regarding the nature of your feelings. Are you just looking to bang? Are you romanticizing the person, making them out to be an idealized version of what they truly are? Is there actually something there? Let an honest assessment of your feelings factor into how you decide to proceed.


JG/Thrillist: How do you ask a friend if you can date his/her ex?

DrCT: Directly. Ask directly, say the words. Inferring, by definition, leaves room for interpretation. Even if it may be uncomfortable, make your desires and intentions known. Though this might not solve everything, it’s a good first step.


JG/Thrillist: How can you tell if your friend is fine with it?

DrCT: This is the main gamble. There is no way to tell what will happen. Your friend may actually be fine with something, but then may change their mind. Or vice versa. The loss of the friendship is something that you have to acknowledge as a possibility going in.


JG/Thrillist: Should you ever go behind their back?

DrCT: This is the only answer that’s simple – no, never.

dating a friend's ex

(pictured: image via Google)

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