Infatuation, love, relationships – it is all complicated stuff. One of the most complicated predicaments you can find yourself in is falling for your friend’s ex. Taboo for obvious reasons, it can be frustrating to have deep feelings for someone off-limits, even if they’re not technically off-limits.
It isn’t easy to start a relationship, with roadblocks like lack of time, low self-confidence, and worries about getting hurt all standing in the way of developing deep emotional intimacy. Because finding love is hard these days, it may feel especially annoying to find a connection you really vibe with, only to have your hopes thwarted because they’re your friend’s ex.
Perhaps your hopes don’t have to stay thwarted, though. We consulted Michelle Cantrell, a licensed professional clinical counselor who specializes in emotionally focused therapy for couples, to provide insight on whether it is ever okay to date a friend’s ex and, if so, how to approach the situation.
To Date or Not to Date?
Things are very rarely a matter of single-word answers. The question of dating a friend’s ex, according to Cantrell, takes four words. “Yes – but it’s complicated,” she says. She expresses the importance of considering context. Dating the person your friend was engaged to is quite different from dating the person your friend had a brief summer fling with.
You’ll also want to think about how things ended. Research suggests that those who have a deep understanding of why a relationship ended tend to have more peace with the end of the relationship. They can also experience a boost in self-esteem. So, if things ended on good terms, it could be easier and far more clean-cut to proceed with a relationship. Things went sour? Think long and hard about the fact that you might sacrifice a friendship if you pursue a relationship here.
“If you care about the friendship, transparency and empathy are key–not just as a formality, but as a genuine act of care and respect,” explains Cantrell. But, before you even get to the point of chatting with your friend, get real with yourself. Cantrell encourages folks to ask themselves if they’re willing to respect their friend’s boundaries if they say they’re not OK with it.
If you care about the friendship, transparency and empathy are key–not just as a formality, but as a genuine act of care and respect,
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MICHELLE CANTRELL, LPCC
If you want to proceed, even if your friend protests, reconsider how you bring the issue up. Asking for permission, even though you know you’ll move forward with dating the ex-partner regardless, is dishonest and unlikely to end well.
Now, there are some circumstances where it is never appropriate to date a friend’s ex. According to Cantrell, relationships where abuse, manipulation, betrayal, or deep emotional wounding were present make getting romantically involved completely off the table. She explained that doing so isn’t just a breach of trust. It can run the risk of retraumatization. No relationship is worth traumatizing someone you care about.
How to Know If It Is a Connection Worth Pursuing
Not all connections are alike, so it is valid if you’re stumped trying to figure out if this crush is even worth all the trouble. Get real about what is drawing you to this person. If it is purely a physical connection, then it likely isn’t worth sacrificing a friendship, which is an obvious conclusion. There are plenty of people you could pursue a solely physical relationship with – no need for it to be your friend’s ex.
But this person may exist in a grey area for you. If you feel this is someone who has potential but isn’t an immediate yes, ask yourself why. Do you like them but are aware of their faults because of what your friend has shared? Are your feelings a lingering curiosity rather than an urgent interest? Are you tamping your feelings down to avoid rocking the boat? Be honest with yourself. “If it is only chemistry or intrigue, is that worth the potential cost to your friendship?” Cantrell adds.
I’m Ready to Take the Plunge—What Do I Do Next?
Even though you’ve made up your mind, spend some time thinking about all the different ways this decision could impact your life. For example, your social ecosystem is bound to get rocked. “If you all share the same social circle – friends, community spaces, co-parenting groups – it can get complicated fast,” Cantrell continues. Being thoughtful about this primes you for what will likely be a difficult conversation with your friend. This brings us to the next obstacle.
(How) Do I Tell My Friend I’m Dating Their Ex?
The key is to have this conversation before you get involved with your friend’s ex. “Not just to ease your own conscience, but because transparency matters,” explains Cantrell. Hiding the relationship is likely to further damage your friendship. When you do bring it up, approach the conversation with care and empathy. Be ready for a strong response. Accept that this might cost you the friendship.
Above all, proceed with integrity. Expressing understanding of how difficult this news may be for your friend, being open to multiple conversations, and remaining mindful of how this impacts the social circle are all important. Discuss boundaries regarding shared social situations and things your friend may not want to know about your flourishing new relationship. Be sensitive to how spending time with your friend and their ex in social settings could be uncomfortable for everyone.
I’m Interested But Am Not Going to Do It; How Do I Tell the Ex?
This depends on your relationship with the ex. If you’ve both already flirted (metaphorically or literally) with the idea of pursuing something deeper, a conversation is warranted. Agree to meet them in a neutral environment, like a cafe, and speak from your heart. Explain how much you value your friendship and you realize that pursuing the relationship is wrought with negative consequences.
Since they are the ex, there is a chance they don’t feel the same level of loyalty that you do – be prepared to potentially not see eye-to-eye on everything. Before you two settle on what you’d like your relationship to look like moving forward, get clear on what you’re comfortable with. If remaining friends runs the risk of blurring the boundaries into an emotionally or physically inappropriate relationship, that is worth bringing up.
TL;DR—What Do I Do?
Before you do anything, talk to your friend about your feelings. Then, consider if you want to initiate a relationship with the ex. If you do, think long and hard about how this will shift things in your social relationships across the board. Discuss all of this with the ex. Decide as a unit if you want to be in a relationship with each other. Keep open communication and check in on boundaries for everyone involved. Most importantly, act in integrity, have fun, and maybe even fall in love.
