An issue that often arises in the early parts of a relationship is whether or not it’s okay to be friends with your ex—or whether it’s okay for your partner to stay friends with an ex. This is a full-length article , so feel free to fast forward to the parts that are relevant to your particular situation.

Before I launch into giving advice, it’s important to get our terms straight.

Key Terms for Dealing with Exes

An Ex: An ex is anyone that you have dated and/or had sex with (or someone you made out with once but really, really wish you had had sex with). The two involved parties will not always have had a title, so you cannot depend on a definition that hinges on the person having been your “girlfriend” or “boyfriend.”

A Friend: A friend is someone you enjoy spending time with, confide in, and can be genuinely happy for when they are in a relationship. A friend is someone whose wedding you can attend without feeling awkward, sad, or angry. You can double date with them, and you do not want to have sex with them.

Staying friends: Staying friends includes such activities as talking and texting on the phone, emailing, hanging out, confiding in one another, and generally having fun together. Friends sit around and do nothing, go out to the movies, go out to dinner, laugh, argue, and cry together.

Getting caught up: Even if your partner does not want to be friends with their ex, there are all kinds of ways they can still be emotionally, physically, and financially involved with their ex. I (and many other people) call this “getting caught up”. Getting caught up includes situations like an ex who continues to contact you (and sometimes your partner), a boyfriend who is financially supporting his ex-girlfriend, and a girlfriend who has to (or chooses to) work on projects at work with her ex. Getting caught up is different from “staying friends” but can be solved in a similar way.

Why do people want to stay friends with their exes?

I myself have been all the parties in the ex-turned-friend situation:

  • The Greedy Diva or The Hedging Dater: The person with a new partner who wants to stay friends with their ex-partner.This is the person who deep down is not completely sure how much they like their new partner or are unsure about how long the new relationship will last. Whether she realizes it or not, the Greedy Diva wants to maintain the relationship with her ex, because this is someone she knows loves her—or at least used to love her…maybe. If it turns out that her new partner does not accept her for who she is, she can always turn to her Naïve Nice Guy for validation (and a quick hook-up).
  • The Duped Damsel or The Naïve Nice Guy: The partner to a person who wants to stay friends with their ex-partner.This is the person who is frustrated with their partner’s friendship with their ex but is shy and confused about how to bring up their discomfort with their partner staying friends with an ex. They don’t understand why their new partner feels the need to stay in contact with the person: “Isn’t this the guy who stood you up on your anniversary?” “Isn’t this the woman who broke up with you because your haircut was ugly?” The Duped Damsel and the Naïve Nice Guy often resort to passive aggression out of a feeling of helplessness concerning their partner’s insistence on staying friends with their ex.
  • The Woman in Waiting or The Side Man: The ex-partner who wants to stay friends with their ex-partner who now has a new partner.This is the person who has not completely gotten over the terminated relationship. He or she will hold on to the relationship—even when their partner has moved on. They convince themselves that they can handle being” just friends” with their ex, but if they got invited to their ex’s wedding, they would have a major freak-out.

But Why Can’t We Be Friends?

If you are the Greedy Diva or the Hedging Dater, do not give me, your partner, or yourself the excuse that you want to stay friends with your ex because they were such a great person you cannot imagine living your life without them. Or that since the two of you separated amicably, there’s no reason you should not be able to stay friends. If you are looking for your life partner, the person you are dating should be the best candidate for a person you cannot live without—not your ex. Staying friends with your ex can jeopardize your relationship in several ways:

  • You will be tempted to compare your new partner to your ex-turned-friend.“She didn’t nag me as much.” Or “He always bought me flowers. Why don’t you?” If you are dating someone exclusively, you have forfeited all rights to compare them to other people. (However, if you are dating casually, I encourage you to date several people at one time, and compare them, but keep these comparisons to yourself.)
  • You may be tempted to cheat with this person when the relationship gets difficult or unsatisfying. None of us thinks that we are thieves, but if a delivery guy was standing at your door holding a steamy pre-paid pizza and you’re still starving after having eaten an unsatisfying, wilted salad, you may just let the pizza man believe that he’s at the right house instead of correcting his mistake. That was a long, complicated way of saying that if the circumstances are right, even very “good” people can find themselves in compromising situations.
  • You will continue to invest time and energy into a relationship that is not sustainable.You need your friends to confide to about the difficult relationship issues that will inevitably arise. Seeking advice from an ex is not only inappropriate—it’s counterproductive. You are simultaneously bonding with your ex over griping about your current partner as well as building a relationship with someone who might dip at any moment—when they finally see the light and realize they are being the Naïve Nice Guy.

Here’s what you should do depending on if you are…

The Greedy Diva or The Hedging Dater: Release the need to have a “sure bet”. This new relationship may blow up in your face just like the last one—or it could turn into a serious, rewarding, lifelong relationship with your perfect math (of course there are options in between, but ya’ll know I’m dramatic). However, your relationship’s development and growth will always be stunted if you are not fully present in your relationship, if your partner does not feel like you are 100% committed to them, and if you are trying to balance and spread your energy across multiple romantic interests (whether you admit that they are romantic interests are not). When Q asked me to break up with my “17 other boyfriends”, I did so without hesitation because I wanted our relationship to work. You can’t hedge your bets once you’ve said yes to being someone’s boyfriend or girlfriend. Hedging is a great strategy when you’re casually dating, but terrible once you have committed to someone. So, Heding Daters, here is your to-do list:

  • Have a frank, concise chat with your ex: “Sasha, I think you’re a great person and you have been a good friend to me. However, I’m really excited about my new relationship, and I don’t want to do anything to jeopardize it, so I’m going to say goodbye now. I wish you all the best in life. Goodbye.” Do not justify yourself to your ex. Do not negotiate with them. Keep it short and get off the phone quickly.
  • Unfriend them on Facebook.This is an important step. You do not want to tempt yourself to check up on them by reading their feed or tempt them by letting them monitor what you and your partner are up to.
  • Remove their number from your phone. We all know how easily drunk dialing can creep up on us. Don’t even give yourself the option.
  • Mourn the loss of the friend. Saying goodbye to a friend is not easy, but it must be done if you truly want to move on. If crying, yelling, journaling, etc. will help you truly move past the friendship, do all these things (in private—not in front of your partner). You need to do what it takes to get over this relationship.
  • Don’t ever mention them again to your partner.The friendship with your ex is now a distant memory. Do not bring it up with nostalgia like your puppy who died when you were 9. Do not brag about it like the Dad in Married With Children thinking with fondness about being awarded his Heismann trophy. Treat the foregone relationship like a past life as a stripper. It’s something you don’t mention because it has no relevance to who you are today and what you are trying to accomplish.

The Duped Damsel or the Naïve Nice Guy: You deserve to date someone who is 100% committed to you. First, say this to your partner:

“I am really enjoying how our relationship is developing. I think we’re getting closer, and learning more about one another. One thing that is bothering me though is that you are still friends with your ex-girlfriend. I’m not saying she is a bad person, but I want to be your best girl friend. It would mean a lot to me if you would let that relationship go so our relationship can really develop without the noise and interference of past relationships. Is that something you will do for me?”

If your partner insists on staying friends with their ex, you should say:

“Your insistence on staying friends with your ex makes me think that you are not completely over the relationship. If you are not sure about who you really want to be with, I would rather you take the time to figure that out before we take our relationship any further.”

This sounds like an ultimatum, and I guess it kind of is. However, it is something that you have to mean and should not feel “bad” about saying. It’s important that in any relationship you never be afraid to walk away from the relationship if you are not being treated with the respect you deserve. You do not have to be dramatic about it. You are just making it clear that you expect to be treated with a certain level of respect. Do not turn this into an argument. Simply look your partner in the eye, say the two lines above without being accusatory, and change the subject. Your partner will get the point—and you will avoid an argument.

The Woman in Waiting or The Naïve Nice Guy: You deserve to have your own relationship—rather than being the sidekick to someone else’s. The great thing about realizing you are the Woman in Waiting or The Naïve Nice Guy is that you do not really have to say anything to anyone. They will get the message when you drop out of their orbit (and Facebook feed and stop answering their calls). However, if you feel the need to achieve closure, you can say:

“I’ve enjoyed our friendship, but I think that it’s better that we not be friends now that you are in a new relationship. I want you to be happy, and I also want to get on with my life, so I’m going to say goodbye now. Goodbye.”

As I advised the Hedging Dater, do not leave the decision up for discussion. Just like breakups, ending a friendship can be a one-sided decision.


The first few months of a new relationship are often very fragile—even when there are not outside people influencing the relationship. If you are truly serious about seeing if the person you are dating is your life partner, both of you have to be willing to cut out the lovers of your past. As your relationship strengthens and the issues and decisions involved get more complex, you will be relieved that you have one less pair of eyes scrutinizing you and one less voice giving their two cents. Release the past now and commit to making the most of the present. That way, you can say you gave the relationship a fighting chance and your entire effort—instead of hedging your bets, being a doormat, or being the stand-by.

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