Staying friends with an ex is tricky terrain to navigate in a new relationship.

Staying friends with an ex can become especially tricky when the “friendship” starts to take precedence over the relationship.

For this week’s Mailbag, “S” writes:

Hi Zach, 

I think what you’re doing is great & healing for a lot of people. Thank you for doing this and sharing your experiences and tips for overcoming RJ.

I don’t think I have RJ in the sense of what I have seen described. I’m not upset about the fact that my partner had a past or what has happened in his past. I am more concerned about the present. 

My partner frequently tells me he misses one particular ex-girlfriend because they don’t talk anymore after he decided he didn’t want to be in a relationship with her. He says he misses the friendship because before they hooked up they were friends since kindergarten.

I don’t mind that he misses her, I mind that he constantly talks about missing her and points out things she would like. Or, when I do something for him, like bring him a gift, he will tell me of a time when she did something better.

He also still talks to his last Ex and has told me that our relationship is 70/30 good times/bad times, where what he had with her is 95/5. He talks to her regularly and used to want to see her, but after some discussion has dropped the idea. 

Another girl he dated, he is staying friends with, and I am fine with that. I’m struggling to understand, though, why he wants to help her so much, above and beyond what people do for friends. He is giving her life advice, and offering to buy her spa packages. He talks about the struggles of our relationship with her, and brings up random stories about her all the time that are often disconnected from the subject. 

On our anniversary he was talking to his most recent ex-girlfriend because her dog died, and talking about this girl he dated and how she is losing her best friend. 

I don’t care that he is staying friends with an ex. I don’t like that he goes above and beyond for them, shares details about our relationship with them, and that they aren’t integrated into our life. I’lll never meet these people, and they will always be separate from what I think we are building together. 

When talking about staying friends with an ex, it always comes back to how jealous I am all the time, how I need to cope. So I’m trying, but is it wrong of me to want him to think more about me than these women? And if they are a big part of his life, why can’t we meet?

I need some help sorting out what is mine and what is his.

Can you help me?

Thank You,


Thanks for writing, S.

There are a million and one things I don’t know about the relationship, about your partner, about you. But while I was reading your letter, a few things jumped out.

First off: it isn’t just you struggling with this.

In the age of Facebook and social media, most modern couples are forced to navigate a complicated, expansive web of social relations with former partners.

There are those who choose to sever all contact with exes, but many more retain at least some contact with some of their exes. “Staying friends with an ex” is a goal many couples aspire to on breaking up.

However, the problem is this attempt at “staying friends” can and often does complicate future relationships.

Secondly, there’s a difference between maintaining some paper-thin Facebook “friendship,” and maintaining an actual, intimate friendship with an ex.

I’m going to assume you and your boyfriend have agreed on sexual exclusivity, but it seems you haven’t spelled out exactly what that means for the two of you.

Here’s an open secret: monogamy is complicated.

staying friends with an ex

Monogamy has always been complicated, but perhaps even more so in this brave new world of hookup culture, dating apps, and social media.

It’s important to keep in mind that everyone’s idea of “monogamy” is a little different; for example, for some people, flirting with others isn’t a big deal, while that would be a deal-breaker for others.

It seems to me that you and your boyfriend lack clear and specific boundaries in your relationship. Maintaining an intimate friendship with an ex might be a deal-breaker for you, S, while it seems like it isn’t for your boyfriend.

Which brings up a good question:

Have you asked your boyfriend how he would feel if you were staying friends with an ex, constantly bringing up your ex in conversation, even comparing your boyfriend your ex?

I’m not sure your boyfriend is all that empathetic.

While we will never fully understand our partners, and they will never fully understand us, it’s a good rule of thumb to approach interactions with others (exes or otherwise) with an attitude of “Would this hurt my partner? How would they feel if they knew I was behaving in this manner?”

This might be a valuable new tool for your boyfriend if he wants to keep you in his life.

You are entitled to your feelings, S, and there’s nothing “wrong” with them. But it’s your responsibility to communicate them to your partner, in a clear and nonjudgmental way.

It seems to me that you aren’t being unreasonable in being a little uncomfortable with the fact that your boyfriend not only is staying friends with an ex, but maintains close, intimate contact with these women. But there are brighter red flags we can look at as well…

My partner frequently tells me he misses one particular ex-girlfriend because they don’t talk anymore after he decided he didn’t want to be in a relationship with her…

…he constantly talks about missing her and points out things she would like. Or, when I do something for him, like bring him a gift, he will tell me of a time when she did something better.

These are very strange comments to make to your current girlfriend.

Of course, if someone was important to us in the past we might have the odd moment of missing their company, but expressing this to our current lover smacks of insensitivity, even cruelty.

Why on Earth would he share this with you? What is he hoping to get out of that? Is he trying to make you jealous?

(A time-tested strategy of insecure people the world over, but we’ll get to that…)

There’s a difference between communicating genuine wants and needs, and trying to hurt someone or make someone jealous. This seems like the latter to me.

He also still talks to his last Ex and has told me that our relationship is 70/30 good times/bad times, where what he had with her is 95/5.

Why did this incredible “95/5” relationship ever end, if it was so fun-filled? Spoiler alert: it wasn’t. It ended. She is an ex-girlfriend for a reason; either she, or he, decided to end things, so I’m guessing it wasn’t quite as perfect as your boyfriend is making it out to be.

Which again raises the question: why is he telling you this?

Only he knows, though he might have to dig deep for the answer, perhaps with the assistance of a good therapist. But regardless of “why,” this kind of low-level emotional abuse isn’t ok.

A good question you can ask him: “If this past relationship was so good, and I’m such a disappointment, why are you dating me?” This isn’t your insecurity talking; it’s a reasonable question, given the comments he makes.

Moving on…

Is it wrong of me to want him to think more about me than these women?

No, it isn’t.

You are his current girlfriend, not an ex. If one of your relationship values is intimacy, communication, connection, it’s entirely reasonable of you to expect that your partner explores all of that with you, and not some ex.

If he’s still hung up on his ex, beyond simply staying friends with an ex, your relationship won’t work.

And if they are a big part of his life, why can’t we meet?

Again, I don’t know the situation other than what you wrote to me, but it seems to me like your boyfriend is trying to “compartmentalize” his relationships a bit. Perhaps he gets sex and devotion from you, and attention and validation from these other women. He might be insecure about his appeal to the opposite sex.

Why do so many men and women post flirtatious pictures on social media constantly? Are they really just trying to “express” themselves? The truth is many of them are just in it for the “likes.” Many of them are insecure–they want approval, validation.

Many of them want to maintain the security, or simply the appearance of “having options” in the sexual marketplace.

Others want “backups:” as in, people they can (and probably will) turn to for comfort in the wake of a breakup. They are terrified of being alone, of having few or no “options.”

Other people may seek attention, validation, and security through other means, such as—you guessed it—staying close friends with an ex.

The truth is I don’t really know what’s going on here, but it seems like neither do you. It’s possible that these friendships are innocent, and don’t mean a whole lot to your boyfriend, but judging by the comments he’s making about them, my guess is something else is going on.

My advice?

Start by asking him a simple question: “Why?”

Why does he feel it’s necessary to make biting comments about how you’re not measuring up to his ex? Is staying friends with an ex important to him? Why does he need to maintain these close connections, and then talk about them all of the time? How would he feel if you were doing the same thing?

Don’t attack, avoid the temptation to be condescending, and don’t judge as you ask; listen carefully when he talks, and really try to understand where he’s coming from.

This is very important: if you are asking these questions from a place of worry, insecurity, or anger, he will sense that, and probably get defensive and cagey.

If, on the other hand, you come from a place of genuine curiosity–genuinely trying to understand the reasoning and perspective of your lover–he will probably sense that, and feel more comfortable being honest with you.

After he’s done talking about his perspective on staying friends with an ex, tell him how you feel.

You’re not being over-the-top, or unreasonably “jealous” here—you’re being honest. (I have an inbox filled with emails from obsessively jealous people, and that doesn’t sound like you.) Express how his comments make you feel about yourself, and all of the doubts and red flags they raise for you. Again, don’t attack, and try to stay calm. Just talk.

Later, set aside some time together, and draw up some clear relationship values, and boundaries. Write them down on paper.

The values can be things like intimacy, connection, open communication, honesty, but these are totally up to you and your partner. The boundaries can be something like: limit contact with exes as much as possible, no physical intimacy of any kind with someone else, no lying, no staying friends with an ex.

Ask each other: what do we want our relationship to look and feel like, day to day?

staying friends with an ex

In a few months from now? What might be the barriers to those goals? Do we want the same things? Be as clear and specific as possible.

You can then use these boundaries and values as guiding lights for your relationship; if you both know your intended destination as a couple, and have spelled it out together, you have a much better chance of actually getting there.

Of course, if you discover that your boyfriend has different boundaries and values, wants different things, or he feels like you’re being unreasonably jealous with your entirely reasonable concerns, it might be time to move on.

Good luck, S.

In addition:

If you are the one choosing to stay friends with an ex, it might be worth asking yourself a few important questions.

1.) What are my motivations here?

Do you really, honestly, in your heart of hearts, value the friendship? Or are you merely having difficulty letting go of a past relationship?

This can be an uncomfortable question to answer, but it’s important.

2.) Is this friendship truly feasible?

Is there still a healthy amount of sexual attraction, or tension, between you and your ex? Or, is there a decent chance you’re just going to end up in bed together again?

3.) Can you be truly honest with each other?

It’s my view that true friendship is based on mutual honesty. How honest can you really be with your “friend?” Could you tell them you’re dating someone new, could they tell you the same?  Could you express anger or disappointment without the friendship exploding into a big fight? Is there still a lingering hurt, disappointment, anger from your former relationship?

4.) Is this friendship fair to your current partner (if you have one)?

Should you really be continuing an intimate friendship with your ex if your priority should be building intimacy with your current partner? Is this “friendship” with your ex costing you more than you realize? How would you feel if your current partner was engaged in a similar “friendship” with their ex?

5.) Is this friendship stunting my recovery and emotional well-being?

In the wake of a breakup or divorce, it can be enormously painful to be faced with reminders of your ex. Needless to say, seeing your ex, talking to them, texting, meeting up for a “friendly” coffee, may all serve as visceral, painful reminders of the love you lost.

This will delay your breakup recovery. So ask yourself: is this really healthy for me? Is this helping me move on, and find someone new?

Breaking up is hard to do.

And staying friends with an ex in the wake of a breakup makes it even harder.

So, if you really do want a friendship with your ex, give yourself (and your ex) some time.

It’s tough to provide a one-size-fits-all estimate, but if the relationship was passionate and substantive, I say give it at least a year.

Once the breakup residue has (mostly) been washed off, you’re moving forward in life, and you have clarity and perspective on why your ex isn’t a suitable partner for you, a friendship might be possible. But probably not before then.

Zachary Stockill
Zachary Stockill

Hi! I'm a Canadian author and educator whose work has been featured in BBC News, BBC Radio 4, The Huffington Post, and many other publications. I'm the founder of, the author of Overcoming Retroactive Jealousy and The Overcoming Jealousy Workbook, and the host of Humans in Love podcast.