You dated someone for years, then mutually agreed to break up. You had a FWB situationship that kind of just faded out. You talked to someone for a few months but never “officially” dated them. Now, you want to start dating their friend. Sometimes that’s OK, but other times it’s not. Take me: I’ve casually dated (read: hooked up with) friends of exes many times, but I’ve never seriously dated an ex’s friend…at least not yet.

Under what circumstances is it acceptable to date a person who’s close with your ex? And how do you navigate that new relationship without causing issues? “It’s useful to remember that different people have different tolerances,” says certified dating coach Elsa Moreck. “What, in terms of dating an ex’s friend, might be perfectly acceptable for one person might be a big no-no for someone else.” She recommends asking yourself these questions before starting something:

  1. How long were you and your ex together? 
  2. What was the quality of the relationship, and how did you treat each other? 
  3. How did it end? 
  4. How were you introduced to the friend you want to start dating? 

According to Moreck, the new relationship might be an issue if your ex and their friend are roommates or coworkers, have been friends for 10+ years, or you were introduced to the friend during a double date with your ex. If your relationship with your ex was super casual, you ended on good terms, or it’s been years since you broke up, then you’re likely in the clear. Still, you want to do so as kindly as possible — aka without breaking any hearts or jeopardizing any friendships.

1. Talk to your ex.

Will it be awkward to tell your ex you’re dating their friend? Yes. Is it necessary to have the talk? Also yes. And depending on your ex’s relationship with your current boo and their feelings toward you, it might open up old wounds. “We often underestimate how much people can handle and assume they’re less resilient than they actually are,” says Moreck. “Do everyone a favor by having the conversation.” You can do it via text or on a call — it doesn’t have to be an in-person thing. Whichever way you go about it, it’ll be a million times less awkward than if they were to find out on their own.

Jess, 28, failed to tell her ex that she was going to start dating her friend, and it ultimately backfired. “My ex and I only talked for a month so I felt like I didn’t owe her much of an explanation, even though I met her friend through her,” Jess says. “When she eventually found out, she flipped out on her friend and ended their friendship.” The friend claimed she wasn’t too close with Jess’ ex anyway, so it was NBD, but Jess still felt awful. Don’t put yourself in that situation.

2. Share responsibility with the friend.

It’s not only up to you to open the lines of communication. “Although you and the ex have no commitment to each other anymore, the ex’s friend still does and will have to take up more responsibility if they want to stay friends with the ex,” says dating coach Cherlyn Chong. If they’re not that close, it may make sense for you to assume the bulk of the responsibility. If they are, consider splitting the load. She recommends speaking separately with your ex in order to make them feel most comfortable sharing their feelings.

When Lucia, 26, and her ex of three years broke up, he was “extremely territorial” and made it known among their friend group that she was off limits. “Years went by, and I started talking to my ex’s friend. He felt that before anything happened between us, he should talk to my ex about it. So he brought it up, and my ex gave him his blessing.” The couple has been dating ever since.

3. Don’t ask for your ex’s permission.

Keep in mind that you’re not asking for your ex’s permission to pursue this new relationship, you’re giving them a heads up that it’s happening so they’re not blindsided. “Informing the ex is more of a courtesy than anything else,” says Chong. “That’s why most people will still date an ex’s friend regardless of how the ex feels about it.” 

When Chris, 29, started dating his friend’s ex, he was upfront about the situation without leaving room for debate. “I basically ripped it off like a Band-Aid. I said, ‘Hey, I’ve been talking to [name], and there’s something there we’re going to explore. I wanted you to hear it from me first.’” This worked, according to Chong, because Chris came off as honest, kind, and concise without mentioning how happy he was. Follow his lead.

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Most people will still date an ex’s friend regardless of how the ex feels about it.

4. Avoid rubbing your new relationship in your ex’s face. 

Whether or not your ex gave you their blessing to date their friend, you don’t need to rub their nose in your new romance. “Ease them into the new dynamics,” says Moreck. This means not making out in front of them, posting Instagram photos of you together right away, or gushing to mutual friends until you know your ex can handle whatever they see or hear.

5. Try not to feel guilty.

“They say all is fair in love and war, but ‘fair’ is a subjective word. Love can be messy, and it can cause people close to us to feel betrayed by our actions even when that’s not our intent,” says Moreck. “Chemistry is hard to predict, and sometimes we feel it when we’re not supposed to. When this happens, it can be easy to feel shame or hatred toward yourself.” Try to suspend self-judgement, and remind yourself that you are being kind and honest in hopes of navigating the situation with grace. 

Jordan, 25, initially felt guilty when she started dating her ex’s friend. “But at the end of the day, I was so into the friend that I wanted to chase my happiness more than anything else,” she says. Reframing her mindset to prioritize her feelings over her ex’s helped Jordan feel better about the situation — and it worked out. She and her ex’s friend have been together for a year.

If your ex tries to make you feel guilty about your actions, Chong recommends “meeting any confrontation with polite, short conversation and walking away from the situation if they want to escalate it.” If you’re having doubts about whether you’re doing the right thing, remind yourself that you can date whoever you want to date. “When you and your ex broke up, you said that you didn’t want to be with each other anymore, and that gives you the right to move on with your life,” adds Chong. That’s true even if it means you’re moving on with their friend.