“Can I Tell My Brother He’s Crazy For Taking His Horrible Girlfriend Back?”

I’m the middle sister between two brothers whom I love dearly and with whom I have complicated but cherished relationships. Last year, our father died tragically and unexpectedly. My mother, brothers, husband and I are still grappling with the pain and shock of his death and have been trying as hard as we can to rebuild our family unit around his absence.

My older brother, “John,” is what you might call a late bloomer when it comes to relationships, career path, and adult independence — he has just begun to come into his own as he approaches his thirtieth year, and, as a result, I tend to feel (and be treated) like the oldest child. John has been seeing a woman I’ll call “Ursula” for the last three years. Initially we were happy to see John entering into his first real relationship – but we quickly saw concerning patterns of controlling and manipulative behavior that forced my brother to walk on eggshells just to avoid fights and turned our family get-togethers into sour, segregated events.

In the years that followed, we did our best to make Ursula feel welcomed into our tight-knit family despite her cold and distant attitude and upsetting behavior towards my brother. Her attitude towards me in particular began to worsen (for mind-boggling reasons I won’t even get into) until it got to the point that she would make snide remarks and passive aggressively pick fights with me at family gatherings while John just looked the other way. I have admittedly mostly tried to keep my distance from her, but, when we are forced to be together and interact, I have done my best to take the high road and treat her pleasantly and politely. But try as I might, her attitude and personality have made it difficult for any of us to genuinely connect with her. However, out of respect and love for John, we kept our opinions to ourselves and let him live his life.

Fast forward to this summer. A few days before the first anniversary of my father’s death (a difficult and sensitive time, to be sure) Ursula dumped John out of the blue for murky and vague reasons. Among many things, she claimed that he wasn’t enough of a “man” who could “support her financially” and give her a “wealthy suburban-soccer mom life.” (For reference, my brother is an introverted homebody who lives a simple life out in the country on a relatively small income, but these are things she has always known about him and pretended to be fine with for three whole years.)

Naturally, John was deeply hurt, confused, and humiliated at a time when he was already grieving anew for my dad. My family and I rallied around him and offered round-the-clock support and advice to get him through and help him see what a blessing in disguise it was. Eventually, he began to bounce back and told us that he realized deep down he’d wanted to end things for a long time but was afraid of being alone (his insecurities and low self-esteem are deeply rooted and tangled up with depression and anxiety). He even started rebound-dating someone else whom he claimed opened his eyes to all of the things Ursula wasn’t: kind, patient, tolerant, laid-back…the list goes on. Recently, Ursula found out he was seeing someone else and decided (after weeks and weeks of silent treatment) to tell him that she wanted to get back together. My brother told me all of this news incredulously, as if it were the final nail in the coffin on their toxic relationship, and we all breathed a sigh of relief.

And then. THEN. Within days of finding out that she wanted to get back together, he went to see Ursula “to talk.” He then promptly dumped the new girl he was seeing and now refuses to answer any of our questions about what’s going on. My mom has gently tried to assess his current feelings towards Ursula, voice our concerns that she is once again manipulating him, and remind him that we only want the best for him (and that Ursula has very clearly demonstrated that she does not have his best interest at heart). He refuses to discuss the situation at all and gets defensive at even the most innocent questions, insisting “You don’t understand – I love Ursula.”

I’m at a loss for words and feel nearly sick at the thought of him bringing her back into his (and our) lives. The last thing I want is a rift in my family, but I no longer feel that I am able to take the high road or “tolerate” her presence. I am deeply, deeply hurt and angered by his decision to go back to her, after everything that’s happened, and I feel that I can’t sweep these feelings under the rug any longer. (My dad even told us, two weeks before he died, that “she has to go.”) I know from other columns that your advice in these situations is to butt out and let him make his own mistakes, but I’m worried about the tension and resentment that this situation could heap on our already-fragile family dynamic (especially since John lives with my mom, whom we try to spend as much time with as possible). Based on her immaturity and his insecurities, I don’t think an open and honest conversation would do much in the way of “smoothing things over” — she has her mind made up about us, and he seems to have his mind made up about her.

Wendy, what should I do? Do we tell him how we feel and risk him choosing her over us? Do we smile and nod and allow someone like her back into our lives as if her behavior is okay? Or is there another way to create boundaries without alienating my brother and dividing our family? — Sick of Ursula

You’re right that my advice in situations like these is usually to let your loved one live his or her own life and make his or her own mistakes, and that’s the case here, too. As much as you may want to, you can’t control whom your brother dates or loves or marries and brings into the family. He already knows how you feel about Ursula since you all expressed yourselves in your support to him after their breakup. You validated him when he said he was realizing that Ursula was not kind, patient, tolerant, or laid-back. Upon their reconciliation, your mother even voiced your collective concerns that Ursula is once again manipulating John, and that didn’t do any good. John is still going to do what John wants to do, and, the more you express your worry for him or your dislike and distrust of Ursula, the more power you give her to manipulate him against you.

I know it sucks and, as much as you don’t want a rift in the family, you dread a lifelong tie to Ursula almost as much. And you know that if John marries Ursula, that’s exactly what you’ll get. But if having John in your life means dealing with her, aren’t you willing to pay that price over the price of losing him if you don’t?

And you don’t know for sure that Ursula is going to be in the picture forever. This is hopefully a momentary blip that will pass as quickly as it began again. As you said, your brother is especially vulnerable right now — you all are — and, as prickly as Ursula is, she represents familiarity to John, which can be especially comfortable when one is grieving. And there is probably also a comfort in their dynamic, as unhealthy and dysfunctional as it may be or seem. Since your 30-year-old brother still lives at home and is, as you say, a “late-bloomer,” I’m going to assume he’s not a “take-charge,” independent sort of guy. He probably feels a lot of security in a partnership with someone who takes the lead and makes the decisions, especially if she is doing so while putting him down and making him believe he’s helpless without her. “Laid-back” (like John’s rebound girlfriend) has its value, but for someone who is very dependent (and insecure), it may actually be detrimental. He needs someone to tell him what to do because he doesn’t have faith that he’ll figure it out or do it right on his own.

So, what can you do? Well, for starters, you can let time do its job of healing all of you and bringing a little more light to what has been a dark period for your family. All of you are still grieving, with an anniversary of your father’s death resurrecting those initial raw emotions and highlighting the enormous loss you feel in your family. He was here, and now he’s not, and, while the pain won’t go away, balance will be restored eventually. You will each take a little of the role he played as your own and will find an equilibrium within your family dynamic again. You could even let John know in what ways he reminds you of your father and how and why your father would be proud of him. Empowerment is a great antidote to manipulation and insecurity.

Along those lines, can John live independently? What’s the reason he lives with your mother? If he had his own place — even a small studio near one of you — he would be better positioned to cultivate some independence, and you would be able to visit your mother without the threat of Ursula being present. Regardless, if he continues living with your mother, then some house rules need to be instated that would create clear boundaries keeping Ursula away. And as long as she is around, I would make plans with John when you know she is unavailable, and I would keep my distance from her while remaining coolly cordial when you can’t avoid her. You managed to do so before and nothing has really changed except the temporary idea that John may have moved on. He clearly hasn’t just yet, so you need to re-adopt the stance you took before and hold onto it as long as she’s around. I think you feel less inclined to do so because you tasted freedom from her and it’s hard to give that up, and you are also feeling the effects of this sad anniversary. Rather than let that weaken your resolve, find strength in it. Choose what traits of your father’s you’d like to cultivate in yourself in his honor. Choose the traits that would fight to maintain closeness with John at whatever cost — even if the cost is holding your nose and smiling at a woman like Ursula. Your father may have said, “she has to go,” but he didn’t mean immediately and he didn’t mean for John to go with her, which could very well happen if you actively try to push her away.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. artsygirl says:

    Hi LW – My guess is that Ursula is likely to exit the picture again in the near future. The things she wants (money, house, etc) have not changed and your brother is not in a position to provide them any more then he did when she dumped him. Has your brother even seen a counselor? If he is facing issues of insecurity, depression, and anxiety which are all hampering him from living a productive adult life, he might need professional help.

  2. girltuesday says:

    WWS. LW, these things have a way of working themselves out. Ursula seems to be after what your brother can’t provide. It seems that she’s trying to mold him into something he isn’t. She’ll grow tired of trying to control him and move on. This sucks, I’m sorry you have to deal with it.

  3. Ursula will be gone again the next time she decides John isn’t independently wealthy enough for her. She only came back to him to control him. Her attraction is based solely on her ability to control him, something she certainly wouldn’t be able to do as easily with someone a little more self-determining. Since John isn’t showing any signs of changing, there’s no reason to believe she’ll stick with him for long. She just wanted to get rid of the new girl. John’s “innocence” clearly makes him a bit of an idiot about love, but you’ll do a lot better with him if you let him figure out that U doesn’t really love him by himself. Meanwhile, there’s no reason whatsoever that you need to take any crap from her. She’s his problem.

  4. Yeah, there’s no way the brother DOESN’T know how everyone feels. He’s even already being defensive about it. So bringing it up yet again won’t help anything. I guess the question then is how much to continue trying to be nice to her vs. ignoring her, pushing back when she says something rude, etc. Nice when you’re forced to be with her is probably still the best bet, to avoid pushing John away. But I think if you insist on seeing him without her more, that could help him realize that he has support outside of her, and would at least save you the headache of having to be around her.

  5. wobster109 says:

    “If he had his own place he would be better positioned to cultivate some independence.”

    What Wendy said, especially this! Your close, loving family means well, but taking care of John is crippling him. My guess is your mother plans family outings and schedules his medical appointments? Does she handle the cooking/cleaning/bill-paying/shopping either by doing them or assigning them to John?

    For me, learning to be an independent adult wasn’t just doing the dishes. It was keeping track of them. Deciding to do them. Getting to a point where I wasn’t living among piles of dishes and doing a big clean once a month. Scheduling my own appointments. And then I started to feel like I knew what was going on, like I wasn’t about to drown every day.

    John doesn’t have the experience or the confidence to see through manipulative people because he’s never had to. My feeling is it would go a long way if he felt in control of his life by trying and learning to support himself, not meaning financially, but domestically and socially. Then he won’t feel dependent on a controlling partner to keep his life in order.

    1. Yes! And what wobster109 said! LW, the more you and your family take responsibility for your brother’s responsibilities – his romantic relationships being his sole responsibility – the less able he’ll be able to learn from them.

      Like Wendy said, Ursula is familiar. Not just in that he has a relationship with her in the past. It’s a reflection of his family life too. He moves from his family doing more than they should for him… To Ursula doing it. I’m hoping “round-the-clock support and advice” isn’t literal. After all, it’s up to him to figure out how to move on and continue on with life.

      A high level of support can make situations seem harder and more catastrophic than it is. Compared that to a spirit of “You’ll move on in time. Seems hard now and it’ll just be a memory. Let’s focus on doing the things we love when we’re together.”

      As for him “choosing her over us”, that’s a false choice. He can choose both. That’s what you should encourage and that’s the essence of Wendy’s words.

      Disengage from your brother’s life. And by extension, having Ursula around won’t seem so bad because you’ll have so much else going on. For yourself, focus on your friendships and goals that are outside of your family. If anything, you’ll be modeling the behavior that you want for your brother.

      He certainly admires you. The best thing to do is take care of yourself and let him learn from that in time.

      1. I just also want to add that dating the wrong person is not the worst thing in the world. For me, I learned a lot from those. They weren’t mistakes. They were lessons!

        If my friends or family ever thought they knew better than me on who I should date… Well, they’d certainly have misunderstood their role in my life.

    2. +1. Wendy and wobster are right. By making the brother live independently there are 2 advantages
      a) The LW’s family does not always have to see Ursula, which will give them at least some tension free gatherings
      b) John will become more independent and can start hopefully making more decisions by himself. That will make either Ursula respect him or leave him altogether. LW family seems to think that Ursula will take over John altogether but that seems unlikely based on the info provided by LW.

  6. dinoceros says:

    Everything Wendy said. The bottom line is that you can’t make someone break up with someone. And even though it sounds like you’re correct that he’d be better off without her, you can’t blame his romantic relationships for your family dynamics. That’s not fair to him. You say that you don’t feel able to take the high road, but you can. It’s a choice. You either treat him with respect and deal with the fact that he’s an adult or you don’t, and it’s totally up to you. You can’t pretend like it’s out of your control.

    If depression and low self-esteem are what’s causing him to cling to someone who is bad for him, getting her out of the way is not the solution. Because there will always be another Ursula. He’s going to have to deal with the root problem. Encouraging him to seek out help and being supportive WILL help with that. Surely you realize that ostracizing him or creating drama will NOT make him feel better about life and himself.

    1. Why yes, I DO realize that ostracizing him and “creating drama” are not the answer – which is why I sought advice for how to handle my resentment towards her and concern for his wellbeing without driving him away.

      1. dinoceros says:

        OK , well, you asked if you should tell him and risk him choosing her over you all (which is essentially the same result). Sorry if you were offended by that, but I was trying to answer your question.

      2. Luckily when they were broken up you had the perfect chance to lay it all out and he listened. So you don’t need to say it again. He’s an adult and nagging is unnecesary. During rudeness, I would tell myself Ursula is a toddler and I’m the adult and be fairly nice to her. Let her focus on deciding / realizing your brother is not the one for her instead of focussing on petty drama with you. I’m sure there is something to learn from her for him anyways. At the very least you learn different emotional and sexual things from different partners. She already dumped him once, he may be sad if it happens but it’s his fault for being fooled twice. You don’t need to warn him , the first dumping was his warning.

  7. I think you’d be best to just play along, being as civil as you can manage to nasty GF, because if he stays with her, he’ll need you to mitigate the deleterious effect she will have on his life, and if they split up, it’ll be easier for him to be open with you if you have stayed as neutral as you can manage. It’s a mystery sometimes why people stay with horrible people despite the devastating consequences, but as far as I can see from experience, you will be able to do the most good for your brother if you stay as close as you can. When it drives you mad, remember that backing off from him now will make Ms Nasty rub her hands with glee. Good luck, however you decide to act.

  8. The most enabling thing you can do towards a dear one is to trust him to make his own decisions. Don’t be judgmental and let him live his life. If you resent this woman or can’t stand her, just be politely distant with her. Tell yourself that your brother chose himself this girl for some reason, and don’t get caught in any script with her. Your family should give this man some space to develop his own life. And you should probably more focus on your own.

  9. bittergaymark says:

    1) Your brother ALREADY knows. (Everybody has said this, but it BEARS repeating.)

    2) Your brother has FAR bigger problems than Ursula…

  10. Alexandra says:

    Speaking from the perspective of a person who was in an abusive relationship – the first people to be pushed away are those who will openly criticize his choice of getting back with that woman (and rejecting him because of it) . Not because he loves you less, but because he feels the need to be around people who understand where he’s coming from. It’s so important when you are in a situation like this to just have a few people who understand your reality. Even if they completely disagree with your choice, but who are still able to say “yeah, I can possibly imagine that I might do something similar”. Because the truth is, you would, if you were in his shoes, if you had his self esteem, if you had many other of the circumstances that shaped him into the human being that he is right now. People who get in abusive relationships are usually people with a very low self confidence, and what will really make them snap out of it in the end is the feeling of being empowered when they are not around the object of their obsession (which the abuser usually becomes).

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