Are There Rules About Dating Your Friend’s Ex?
Whether it’s OK depends on several factors, Nari Jeter, PhD, a licensed marriage and family therapist in Tallahassee, Florida, tells MyLifetime.
Dr. Jeter says those include your relationship with this friend, their relationship with their ex and the details surrounding the breakup.
For instance, if you and this friend are merely acquaintances or the friendship is more casual, that’s typically safer territory. When that’s the case, Dr. Jeter says, also consider: “If their relationship wasn’t very serious, happened several years ago and your friend has moved on to a new relationship, that’s an ideal scenario to be able to date their ex.”
However, things get more complicated if you’re very close with this friend. The same goes if this was a long-term relationship, they were married or they have children together. These terms often lie closer to no-go territory—says Patricia Dixon, PsyD, a psychologist in East Palmetto, Florida, “There are going to be relationships that just mean too much or were too serious that no amount of time will erase the impact of dating your friend’s ex.”
In addition, how their relationship ended can also influence things. An amicable breakup is a very different situation than a relationship that ended because of betrayal or lingering heartbreak. If the relationship involved infidelity or emotional or physical abuse, proceed with extra caution. Even if your friend has moved on, those experiences can leave lasting emotional scars. Plus, you don’t want history to repeat itself.
Signs Your Friend Isn’t Over Their Ex
Both therapists say that the nature of the relationships—both between you and this friend, and the one between your friend and their ex—matter more than how long you wait before considering beginning this new relationship. That said, more recent relationships (as well as messy breakups) might still have fresh wounds. Even if their relationship ended years ago, time alone doesn’t tell you whether your friend has truly gotten over it.
How emotionally healed your friend is will factor heavily into things, Dr. Jeter tells MyLifetime. If your friend isn’t over their ex, it’s probably not wise to pursue the relationship if you want to remain friends.
Unsure if your friend is actually over them or they’re just saying they are? According to Dr. Jeter, they still might have feelings if they frequently talk about them, compare them to their new partner, check their social media often, or express regrets about the relationship ending.
How to Tell Whether Pursuing the Relationship Is Worth It
First things first: Carefully weigh the factors above. Pursuing the relationship could end up changing or even ending your friendship. Tension could even trickle down to your mutual friends if they choose to take sides, Dr. Jeter says. While that’s not always a reason not to move forward, it’s a reality you’ll need to accept.
“Before you even let yourself consider dating your friend’s ex, ask yourself how much you value your friendship,” Dr. Dixon tells MyLifetime. “Can this person you're interested in replace that?” The answer may be complicated, but it’s worth being honest with yourself before emotions take over.
You should get curious about the person in question. Do you already have a solid connection? Is this someone you see as a potential long-term partner? Or are they simply familiar and you’re enjoying the attention they’re giving you? Answering those questions honestly can help you decide whether this relationship is truly worth what you might stand to lose. Naturally, the risk likely isn’t worth it if it lacks the potential to turn into something meaningful.
How to Bring It Up With Your Friend
If you’ve done some soul-searching and come to the conclusion that this relationship really is something you find worth pursuing, approach your friend directly—and ideally, before you start dating. You don’t necessarily need to ask their permission. In fact, Dr. Jeter says doing so could actually make matters worse. “It’s not fair to make this solely your friend’s decision; you must acknowledge that you’re making a choice as well,” she says. “Putting the weight of this completely on your friend will create tension or resentment.”
Above all, make the conversation about honesty and openness—not convincing. Dr. Dixon suggests validating the friendship first. Let them know what they mean to you and that you’ve put thought into their feelings. From there, she says you can lay your cards on the table.
To approach the topic carefully, Dr. Jeter advises saying something like: “I’m interested in X. Because you’re important to me, I wanted to talk to you about this before I pursue anything. You don’t have to tell me now, but I want to know how you feel.” Then give them space to process. They might have follow-up questions. They might be shocked or upset. Or they might brush it off and give you their blessing.
Just pay close attention to how they respond—not only what they say. Their body language, tone, and emotions will tell you more than their words alone, according to Dr. Dixon.
Is It Possible to Stay Friends If You End Up Dating Their Ex?
Both therapists say it’s possible to maintain your friendship if you end up dating their ex. (That is, so long as your friend is actually OK with it and doesn't feel a sense of betrayal.) However, the dynamics of the friendship might shift. “Even with their blessing moving forward, it’s reasonable to expect things to change in the friendship,” Dr. Dixon says. They might become more distant, or things could feel uncomfortable for you both at first. That said, you’ll want to start this new chapter with extra care, intention and mindfulness.
Dr. Jeter suggests it’s wise to clarify boundaries and expectations up front to avoid conflict or resentment. For example, they might ask not to hear details about the relationship. Or maybe they won’t want to hang out with you both in group settings. “There is no one-size-fits-all list of instructions,” says Dr. Dixon. “You just need to sit down and discuss what you’re specifically comfortable with so that you're not creating any unnecessary awkwardness.”
Also know that the situation is dynamic: Your friend’s feelings may change over time. Perhaps they thought they’d be fine with you dating their ex, but once that happened, sadness or jealousy took hold.
Or maybe they really are OK with it, but they simply don’t want to witness you two being affectionate in person. If maintaining this friendship is important to you, check in with them and have another chat if it seems like they’re upset or your friendship is heading in the wrong direction.
“Invite continual conversations and welcome complicated feelings without defensiveness,” Dr. Jeter advises. “Remember that people who care about you can feel multiple feelings at the same time, such as happiness for you, but also grief or envy.” Giving your friend room to experience those conflicting emotions can go a long way, even if the situation remains uncomfortable.
There may not be a version of this situation where everyone walks away completely happy—and maybe that’s okay. Even if you’ve handled everything thoughtfully, your friend might decide they can’t continue the friendship. That’s painful, but it’s also their choice. While you ultimately can’t control how they’ll respond, you can control whether you’ve acted with honesty, empathy, and care.
