How Close Should My Boyfriend Be With His Ex?

man in between two woman, one holding close to his arms

This may be an age-old question. My boyfriend is best friends with his ex-girlfriend. They dated for two and a half years, broke up 5 years ago, have many mutual friends. They met in graduate school and went through some hard times together, so I understand why they stay friends.

However, they are way too close. They talk on the phone 2-3 times a week, meet up for lunch/dinner. My boyfriend once told me she’s so important to him that if we ever get married and have a house, she would be invited to our house for holiday dinners. The first time I met his mom, she could not stop talking about the ex. She told me their entire dating story, why they broke up, how the ex-girlfriend’s parents still think my boyfriend is the best guy for her (oh yeah, the mom is also good friends with the ex girlfriend’s parents). Of course, I was annoyed but maintained my cool. I did have a discussion with my boyfriend after this incident, and he thought his mom was inappropriate.

The ex-girlfriend also will not stop posting on his Facebook wall almost daily, with intimate posts (“awww… your stress won’t last much longer”), pictures of their families having thanksgiving dinner last year before we started dating, pictures of them dancing together back in graduate school, etc.

I don’t think her intentions are pure. I trust my boyfriend 100% and I really don’t think he’ll cheat on me with her. I just think the whole situation is disrespectful to me and her behavior is very inappropriate. He’s letting her do that to me and to our relationship. He refuses to distance himself from her and thinks I’m being unreasonable by asking him to do so. I have met the ex-girlfriend. She was extremely nice to me, so much so it felt unnatural since she doesn’t know me at all.

So, my question is what kind of friendship with the ex is too much? Where do we draw the line? Am I being a jealous girlfriend to feel the way I feel? I have dated guys who were on civil terms with their exes and I was even friends with the exes, so I really don’t think I have jealousy or insecurity tendencies, it’s just that this situation makes me really uncomfortable. —Irene

Some men are better boyfriends than husbands.

Dear Irene,

Your story reminded me of someone I know — a female friend who has a similar relationship with her ex-boyfriend. It seems pretty clear from the outside that the ex-boyfriend is her best friend and “soulmate”, while the husband is merely the father to her children. The husband provides money and stability, but they don’t truly connect the way she does with her ex. The husband seems to accept this and there is virtually no probability that she would leave him for the man she dumped seven years ago. Some men are better boyfriends than husbands, she concluded. And she’s right.

Which is why I’m not willing to go out on a limb and suggest that you’re in the same situation. After all, I don’t have all the facts. Among the important ones:

How old are you? 35-year-olds are usually better decision makers than 25-year-olds. They’re often better able to separate relationships into different components and can see things clearer in retrospect. I have a number of girlfriends that I’m appalled that I ever dated, a handful of girlfriends who were wonderful whom I didn’t appreciate, and a few girlfriends that really, would have been better off as friends. I’m guessing this guy is no different.

How long have you and your boyfriend been together? If you’re a recent couple, you don’t really have a right to say anything about how he lives his life. You don’t have any leverage on a man until he loves you, and the more you pressure him to change, the less likely he’s going to be busting out the “L-Word” any time soon.

Nothing makes a man want to cheat (or leave) more than a girlfriend who doesn’t trust him.

And the most important fact that we’re not privy to…

Who dumped whom? Usually, the person who got dumped is the one who still wanted to be in the relationship. The person who did the dumping is the one who thought long and hard about whether it was a wise decision to end a 2  ½ year relationship. If your boyfriend concluded that, all things considered, his ex was not a good fit for him in the longterm, whether its due to different views on sex, money, religion, or personality conflicts, then that’s all you need to know. Ask yourself this: would YOU take back anyone that you’ve dumped? That’s right. Neither would we.

And the real truth is that I wouldn’t take back anyone who dumped me either. Sure, at the time, I was reeling, and wishing things could be different. But then the smoke began to clear and I started to see my ex’s for what they were — normal, flawed women, not visions of perfection like I made them out to be. So even those who dumped me wouldn’t get a second shake today. Think about the men who dumped you and whether you’d truly take them back. I’m guessing you wouldn’t.

At the end of the day, it’s not my place to say whether they’re “too close”. Two to three times a week does seem excessive, I’ll admit. What I would probably suggest is that if you’re “the one” for your boyfriend, he’ll start to show it in his actions and won’t want to spend as much time and energy on his ex. You won’t have to say anything at all to make it happen. If you find you’re not getting your relationship needs met, you can leave. In the meantime, get out of your own way. You’re getting yourself tied up in knots and it’s surely not serving your goal of maintaining a healthy relationship with your boyfriend.

You’re the one who just said you trust him 100%.

You’re the one who said he won’t cheat with her.

How about you start living your life like it?

Because nothing makes a man want to cheat (or leave) more than a girlfriend who doesn’t trust him.

As I’ve said many, many times before, it’s either full trust or no trust.

What do you think is going to lead to a better relationship.

And if anyone wants to get on my case about telling her to accept her boyfriend’s behavior, please go back to that paragraph where I said that if she’s not getting her relationship needs met, she should leave. But if she’s GOING to be in the relationship, the way to handle it is to be trusting, not edgy and jealous.

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  1. 1

    yikes- that situation would drive me batty and there’s no way I could personally handle my boyfriend being that close to his ex. That’s just me though.

    1. 1.1

      I totally agree. I would have to come first.

  2. 2

    Wow, I give you kudos for responding to it in what seems like a pretty enlightened manner.   If it were me I’m with Cheryl- I’d be pretty upset!
    The bottom line here seems to be that he knows how this situation with his ex makes you feel (since you’ve told him), and it’s up to him to either do something about it, or not.
    On your end, you have to decide if you’re OK with his actions (or inaction) on that front.   Like Evan says: if this guy isn’t giving you what you personally need to feel secure…well, after letting him know your feelings and giving it some time, all that’s left is to leave.
    I’d advise maybe taking a step back, getting into your own hobbies, hanging out with some friends…put yourself in a happy place and see where this goes.

    1. 2.1

      Thats what I have to do is take a step back. My bf’s ex is constantly on our facebook conversations and on his timeline-Ive told him several times and he just wont discuss it. If it doesnt change, I dont know where this relationship will end up. MY feelings should come before any EX’s!


      1. 2.1.1
        Karmic Equation

        Desiree, you have every right to say something to the ex if you believe she’s crossing a  line.

        Why don’t you tell her to stop her inappropriate behavior?

        There’s the rub, right? She’s not behaving inappropriately. You just don’t like it. You’re jealous.

        It’s not your bf’s responsibility to assuage your jealousy.

        If HE is behaving inappropriately, then you ask HIM to stop. If he doesn’t, he’s wrong.

        But   him asking  his ex stop HER behavior because YOU’re  jealous is not a good enough reason. As I wrote, if she crossed a line, you’re within your rights to tell her off. If otherwise, you need to let it go, or let him go. Not nag him.

        1. sam

          Thats so wrong, saying: “it’s because she is jealous.”

          She doesn’t have to be jealous to feel uncomfortable about the situation.

          If any boyfriend or girlfriend is more concerned about a relationship they have with an ex than the person they claim to love.

          It is neither healthy or fair.


      2. 2.1.2

        I totally agree. I got upset because my finace was always talking to his ex- behind my back and then lying about it.   I left for a while and after a lot of conversations,   I did forgive+ however, the trust is broken and slow mending. If it happens again- I will be gone for good- no more chances. Everything has been put on the table now, there is no question what my bottom line is- if I am disrespected, all I can do is leave for good and respect myself.

  3. 3

    On the one hand, what Evan says makes perfect sense.   I am pretty good friends with my ex husband, but I know that I could not ever live with him again.   His current wife knows this and is not threatened by it.   I get along with her quite well too, but have not ever knowingly given her a reason to suspect me.

    That having been said, if this sort of situation makes me feel that uncomfortable, I’m walking.   I agree that it’s best for the OP to get out of her own way and stop tying herself up in knots, but to me the best way to do that is just bow out gracefully and move on to a guy who doesn’t have such close ties to his ex.   But then I tend to be an avoidant personality type anyway.

  4. 4
    35Y old here :)

    I bet he was the dumper. The “reason” must have been bad timing, financial/career issues that “made it impossible” for him to commit to her. Slow, dragged-out breakup ensued. Then they got back together as “friends”, after the period of time required to soothe the terror he felt vis-a-vis intimacy. In fact, now it is perfect for him, as his relationship needs are completely satisfied (what can be better than two lukewarm half-relationships to someone who is batshit scared to have both feet in one relationship, with one person?). He is going to play this Ex card to not commit of LW. The three of them may merrily continue this way, but worries that LW will need to cook for the ex during family holidays are pretty much unwarranted: he is not the marrying kind. The biggest threat to everything ending abruptly and badly: when the ex grows up and falls in love with someone else.

    1. 4.1

      Bingo!   I just excused myself from a similar situation.   As soon as I mentioned I wanted something more from the relationship… dude ditches me on a Friday to meet up with an ex-girlfriend.   When I inquired, it’s “I’m not ready for a serious relationship”.   Queue my exit, ” okay well I’m not comfortable continuing as we are ” (three months, physically intimate).   I’ve studied a lot of psychology and I know this ploy.   You toss in a third person or thing (could be work, drugs, in-laws) to ensure you don’t get truly intimate with your partner.

      I’m pretty bummed about it.   And maybe haven’t handled it well… of course he’s hanging out with said ex a lot now, they’re flirting incessantly on Instagram AND of course he’s online looking for younger women.   Because, you know, gotta keep that triad up.   Make sure you get your needs met by more than one woman.



      1. 4.1.1

        That’s why, girls and women, do not sleep with a man until he can promise you and show you a commitment !   3 months is too soon.   Most girls get intimate with a guy on the 2 or 3 dates !   That is rediculous!   They are only out to chase women, as soon as they get to the second base, goal is accomplished.   They are just using you for their convinence.


        Ladies, do not believe their BS !   If a guy comes on too quickly physically, kissing and touching in the first 3 or 5 days, they are out to play !

    2. 4.2
      nic L

      What is LW ?   I think you are right !

  5. 5

    When my exhusband and I were dating he had an old flame like that.     Always present, showed up unexpectedly at events she knew we would be attending, dropped in on him at the office, always keeping him up to date on her family happenings and occasions.   Reacting to me with cool acceptance.   Obviously had a hidden agenda.    

    So I asked him frankly about her “Does Ann still have feelings for you?”     He replied that he had not thought about it   because they had been friends so long but now that I had brought it up it was something that was worthy of assessment.     So he made a conscious effort to gradually create some distance.   She became resentful of me but eventually got the message and also lessened her contact.  

    So it might be worth the effort to discuss this with your boyfriend and if you are uncomfortable with the exchanges let him know this.   He might be willing to adjust his behavior.

    1. 5.1

      I’ve been absent from two of my ex girlfriends life for 20 years. We dated when were 16 and 17. Many people might take the high road so to speak and say “I would be this or that.” But you can’t pick you ex’s. All of your girlfriends or boyfriends will become ex’s sooner and later. When they do. They do all sorts of things.

      My ex and I began talking on the net. Bad idea. We were different people back then. We were in highschool, just graduating from highschool. At the time, when we dated, she was great. Always funny, cute, and easy to love. But now when ever we talk she thinks communicating includes yelling, cussing, swearing at me if I have a different opinion.

      One of the things I have learned about my ex’s. Is time doesn’t heal wounds, it makes our problems worse. Much worse. We don’t have sex between us anymore, we don’t love each other, hell we don’t like each other. Ex’s generally don’t get better with time.

  6. 6

    Dear Irene,

    Been there. I also thought my boyfriend at the time wouldn’t cheat on me, but I didn’t trust her, too invasive, too “hey, don’t forget me, happy for you and your new girlfriend, but don’t forget me”. She was the one who dumped him after NINE years together, and one day she woke up and told him she wanted him back. He didn’t hesitate, not even for 24h.

    He cheated on me and then dumped me over an e-mail while I was at work (yes! He did that!). Just like this, I couldn’t understand what was going on, since we never had a fight, the only problem was “her”, all over the place. Then I found out he cheated on me with her. And he even tried to make it look as if he did what was correct, ha!

    My advice? If you’ve been together for a short time, just like Evan says, wait and see. If things don’t change, find a guy who has a normal relationship with all of his exes. You will lose NOTHING if you lose a guy that doesn’t respect you and your relationship.

    Please, don’t wait too long, you deserve a good boyfriend with no intoxicating ex…

    1. 6.1
      Torsh Johansen

      I like your view.   I would say wait and see, too — but in between seeing & leaving, I would say bringing it up.   Plus — how long is “too short”?   I mean, this isn’t about telling someone “how to live one’s life”.   This is gauging on what’s up between them.

      If someone is still like peas & carrots with their Ex like that, there’s some feelings that they themselves may not be aware of (but usually do with a few drinks in them).   Doesn’t mean they’ll Physically Cheat or anything — but that’s not required.

      I personally would say hitting the 3 month mark — you definitely have to bring it up to the bf/gf in a good way by not coming off as paranoid or whatever, because many times they’ll probably want to peg you that way out of defense.   You let them know that it’s not a small deal, but you’re not going to be fighting all the time about it, etc.

      And if you see their loyalty to their ex to be so cozy with them not change?   You just pack it up and leave…

  7. 7

    To me, this seems abnormal behavior. If it’s a short relationship between the LW and the guy, then I agree that he shouldn’t dump his friends for a new girlfriend. However, I think it’s a fair generalization to say that a large percentage of people would feel uncomfortable if their new partner was talking to an ex 2-3x a week. Even if I was really good with my ex’s (I’m not friends with them at all), I would try to keep the friendship at a certain distance to not make potential new partners question me, like the LW is doing to her boyfriend. It just make sense to me… it’s almost kind of like a social grace. If they have been dating for a while, and if he wants her to be okay with the situation, he should compromise a bit too – maybe talk to her less. It’s not really fair to say “you’re just sensitive, learn to deal” when you apparently are trying to sustain a relationship.

  8. 8

    I agree that the situation is disrespectful and inappropriate, and think that the level of interaction he has with her is way more than reasonable.   I do agree with #4 to some extent… it does seem like he is having an emotional relationship with her and a romantic/physical relationship with you.
    BUT before I go dumping him, I think it is fair to do what Venus #5 did, and request he pull back, only on the grounds that you are picking up a “She’s still into you” vibe.   His comment about “If” you get married (the big IF…) that she would come for holiday dinners is nuts.   She has a family!   That, to me, reads like he is trying to hold some power card in the relationship, and knock you down a peg, whether consciously or subconsciously.

  9. 9

    This is such an interesting question. I’d love for Irene to head over and get myhonestanswer!
    I think Evan is on the right track though – you either trust him, or you don’t. You can’t only trust him around certain people. That isn’t trust.

  10. 10

    I would not tolerate a new or old boyfriend hanging out with an ex girlfriend. The family was totally inappropriate when they met the new girlfriend, and he clearly is not boyfriend material. Keep looking, it’s a heartache in waiting.

  11. 11

    Wow, I had a similar situation with a boyfriend. The ex just couldn’t let go, became obsessive, and even engaged in some weird, stalkerish behavior, like dumping things at his house and incessant hang-up calls (in the days before caller ID was everpresent). He wore up, down, and sideways that he had no interest in her other than friendship, and told me he dumped her because their romantic relationship sucked. Eventually, he broke up with me, and guess what? He ran straight back to her, and they ended up getting married. I realized later that he was secretly flattered by the attention, which isn’t exactly the healthiest response either.

    I disagree that people do not get back together with their exes. In fact, it happens all the time. If Irene and her boyfriend are really a solid couple, the ex should be hanging out with both of them.

  12. 12

    Time may tell. If it seems that this new relationship isn’t advancing, then it sounds like the BF hasn’t let go of his ex. I think this girl should just keep her eye open for new guys if it seems like closeness this is going to still happen. Better to be with someone who has moved on than not.

  13. 13

    Sorry, what LW describes is not  friendship with an ex — because those types of friendships have  healthy boundaries, which I’m not seeing in this situation.    I’m totally in agreement about the complete-trust or no-trust philosophy and the ugliness of jealousy, insecurity, possessiveness. I also believe  that the best kind of ex is one with whom you’re on friendly terms. But I also  think  truly healthy relationships can only grow when  both people are  ready and willing to let go  of the past, ugh to move on and invest 100% in the new relationship.  The Be-Here-Now mode of living & thinking.

    That’s my mature side talking. In  more crude terms: Boyfriend  needs to you-know-what or get  off the that  cozy little pot he’s occupying.  Pretty safe to say he has  no plans to  do  either, because apparently he requires  the intimate connection of 2 women in order to have his “full spectrum” of needs met.  Without judging that,  (Har!)  and based on my own experience with this kind of situation,  this  is a hands-down double-dealbreaker for me. It involves his inability to disengage from his old girlfriend  (and to me, who dumped who  is irrelevant),  coupled with the  enmeshed families’ intrusiveness.    Oy.

    As they say, life’s  short. Find someone who’s happy as  a clam having just wonderful you  sharing his  primary intimacy needs, and leave this selfish  momma’s boy  behind.

  14. 14
    Annie Gleason

    I think Evan is on the right track. I have a suggestion that might help Irene to feel at ease with this situation.
    Try to make friends with the ex. Ask her to go to lunch or coffee, tell her that you’d like to get to know her, but that you’d rather not discuss the boyfriend. Then talk about everything else you have in common. Change the subject when his name comes up.
    This worked wonders for me and my ex, who is also a close friend. When he and his fiance got together a dozen years ago, she and I bonded over business, gardening, dancing–whatever we had in common (aside from him.) We socialize   together as a threesome and with each other one-on-one. She knows that I totally support her and their relationship because she and I took time to establish trust and our own friendship.
    It’s awkward at first, but Irene will soon discover where the ex is coming from, and, if all is on the up-and-up, she will likely make a new friend. Her boyfriend will feel more relaxed about the situation, because he won’t be caught in the middle.
    Annie Gleason, Midlife Dating Coach, Get A Love Life

  15. 15

    Zann, your advice is always golden.   Love when you comment!
    I have only been able to remain friends/acquaintances with exes when there was no real emotional bond.   If there was, at least one person probably got hurt, and before A LOT of time has passed, a friendship will be complicated, at best.   Sounds like boyfriend’s ex– and his relationship with her– are way too present in his life right now.   It’s not necessarily that he will cheat; it’s just that he might not be emotionally available.   Irene should proceed with caution.

  16. 16
    Flower White

    If she desires a stable dependable non-dramatic relationship then she needs to dump him and move on.

    WHY do we women waste time with the obvious? It’s toxic too much nonsense say goodbye.   Odds stacked against this. Better odds in Vegas!

  17. 17

    I was in a relationship like that. He was getting his physical and romantic needs met by me, and his need for emotional intimacy met by another woman.

    When I ended things, he ended things with the other woman also, and fell in love with some-one completely different.

    Most important question you can ask yourself, are your needs getting met?

  18. 18

    If Irene can reach a level of acceptance with this and she is sure in her heart there’s no jealousy, then she might be able to move forward and even develop a strong friendship with the ex gf.   However, if she will be plagued by insecurity and jealousy let it go.   Do not stay in any situation that perpetuates those emotions as they are toxic and destructive.

  19. 19

    Beware of the ex!!!   At least in my neck of the woods (Italy), the ex-girlfriends are VERY aggressive and competitive, and they pounce just for the sake of pouncing, whether they really want the guy or not.   It’s a lack of respect towards the current girlfriend any way you look at it.   Jealousy or no jealousy, there is nothing that makes me more mad than feeling disrespected.   I’m lucky not to have had such drama with my current boyfriend, who has taken the initiative and demonstrated that he wants to be with just me.

    I think that trust is one of the biggest gestures of love that exists, but at the same time, I have learned not to ever step aside so that someone else (an ex, for example) can “take the stage”.   If it feels really bad in your stomach, do what you need to do to feel better.

  20. 20

    P.S. I am best friends with an ex, and he is getting married this year.   When I saw how excited he was to start dating her and brought her around to meet his “posse”, something that he simply doesn’t do with just any girl, I turned my focus to getting to know HER, and to leaving them alone, as a gesture of respect to her and to the new relationship.   In the end, she and I have bonded quite a bit, we really like each other, and they have asked me to be in the wedding! 🙂   I am absolutely thrilled. Anyway, she is a very secure, relaxed girl who doesn’t seem like the jealous type anyway, but I like to think that because I stepped waaaaaaay aside and stayed out of the way, I was able to earn her trust and pretty quickly too.

    1. 20.1

      Girls want attention, women wants respect. You are a selfless woman, that’s very rare and the best kind of friends also the best kind of ex, that ‘s why they respect you.
      Girls should learn this.

    2. 20.2

      I love this response!   I have been the ex and reacted in the same way.   It honestly felt disrespectful to the new person not to give space.   Now that I am the new person and feeling guarded about his ex, I have additionally considered that her low effort to try and know me feels odd, at best.   Very early on, I was forced to meet and hang out in a group  when we met, because I barely even got the heads-up that this was an ex.   My partner admits to hoping we’d hit it off before he told me of their past, but luckily, he got better advice at the last second!   Nevertheless, she was the center of attn most of the night because of recent celebrations in her life, and she spent more time thus impressing my friends than asking me ANYTHING about myself.   In fact, the only comments I received were aimed at what I don’t know (as well as her) about my new partner.   I felt so trapped and manipulated, but I know I can’t direct my frustration at her.   I’ve been very clear to my partner how difficult the situation was and that trust is more challenging now.

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