Dear Wendy
Dear Wendy

“My Boyfriend’s Sister Wants to Break Us Up”

My boyfriend, “Jim,” was off-and-on (mostly off) with his ex-girlfriend, “Gayle,” for close to a decade. During this time, Jim’s sister, “Rebecca” despised Gayle. After his and Gayle’s relationship fell apart yet again — with Gayle stealing a considerable sum of money from him — Rebecca and Gayle have suddenly become inseparable.

For the first six months of our relationship, Rebecca could not separate her friendship with Gayle from her relationship with Jim. She actively tried to help get them back together and for months belittled and ridiculed Jim’s and my relationship. During this time, Jim and I continued trying to be nice, inviting Rebecca to dinner, etc., until the torrent of texts, calls, and visits from Rebecca and Gayle became too much to handle and he blocked both of their numbers and cut Rebecca from his life.

Jim’s family is very large and VERY close, so, as you can imagine, this completely divided his family. Rebecca played the sympathy card and gained the support from pretty much all of her and Jim’s family (the females, at least). I should mention that Rebecca has a young daughter who is the complete center of the entire family, so really whatever Rebecca wants to do she gets away with without anyone questioning her actions [examples edited out per the LW’s request, but relate to Rebecca’s romantic relationships and scenarios that affect the family’s finances — Wendy].

Rebecca has never made any effort to reconcile (or even apologize), and eighteen months later Jim’s family still continuously go on about how he needs to “let it go.” Yet, Rebecca is still friends with Gayle and I am sure, given half a chance, the two of them would try to destroy our relationship all over again.

This whole situation is such a strain on us all and I simply do not know how to handle it as both our “kill them with kindness” and our “ignore it and they will get bored” approaches have just not worked.

Jim actively talks about our getting married and having a family in the future, but it breaks my heart knowing that, however long we are together, Gayle will always be more a part of his family than I am — something which I am quite sure may be the undoing of our relationship.

I need some straight-talking, non-biased advice, please! — Not Accepted By His Family

Well, yeah, if Jim has a VERY close family and the two of you have cut off the center of it, then probably, yeah, you won’t ever be very close with his family and it may very well be the undoing of your relationship. I mean, what did you expect when you cut off Jim’s sister? That everyone else in the family would just embrace you with open arms and it would be NBD?

If it sounds like I’m coming down on the victims here, it’s because your story sounds like it’s missing something and, without knowing what that something is, I have to assume you played some sort of role in what’s gone down. I mean Rebecca despised Gayle for years, Gayle and Jim broke up with Gayle stealing a considerable amount of money from Jim, you enter the picture, and then suddenly Rebecca and Gayle are inseparable and have joined forces to break up you and Jim?! Something just doesn’t add up. There must have been an inciting incident to cause Rebecca, who had previously hated Gayle, to suddenly prefer her over you. Do you have any idea what that something might be?

And not only did/does Rebecca prefer Gayle for her brother over you, but she also has actively tried to break up you and Jim. That’s just not…. normal. And if that is totally coming out of nowhere, then you have my total sympathy. But some of the way you talk about Rebecca — which I edited out, per your request — makes me suspicious about your feelings of her coming into the relationship and whether there was a relationship between you that you aren’t mentioning or that you had preconceived ideas about her that affected the way you treated her. Her personal relationships, for example, are really none of your concern, or anyone’s concern, and yet you classify them as “actions her family lets her get away with.” Well, yeah, I would hope a family would let a grown woman “get away with” divorcing her husband, for example.

Also, I question how strong your relationship is with Jim if you are truly scared that his sister and Gayle have the power to “destroy” your relationship. Why else would you even care about what they might throw at you guys unless you were really worried that something might stick and that you and Jim could break up over something the two of them said or did? If it were my husband and I, for example, and someone were trying to “destroy” our marriage, I would be angry, sure — I’d be annoyed and be hurt — but I can’t imagine anything anyone could say or do to “destroy” our relationship. We trust each other, we have each other’s backs, we’re committed. That’s something that I know a “torrent of texts, calls, and visits” wouldn’t stand a chance against. If you and Jim are talking marriage, your relationship should be strong enough to withstand some texts and phone calls from his sister (especially since you don’t have to answer them!).

Finally, you say you that “it breaks your heart knowing that, however long you are together, Gayle will always be more a part of his family than you are,” and I’m not sure what that is in reference to. Gayle is friends with Rebecca, but does that mean she’s at family gatherings and being embraced by everyone else in the family? Has that always been the case? Are other members of Jim’s family, besides Rebecca, making their preference for Gayle over you known? Again, I have to wonder why that is. That’s just not very normal behavior outside of affairs that end marriages (and especially marriages with kids involved). In those cases, the “other woman” is sometimes treated coldly by family members for a while, and the alliance is clearly with the ex-wife. But Gayle and Jim weren’t married, and you don’t mention any children between them. So…. I just don’t get it.

If there is more to the story here, I’d love to hear it. But without more details, I have to say that if you really want to be part of Jim’s life and his future, knowing that family is a super important part of his life and worrying that not being accepted by his family will ultimately be your undoing, then I think you need to start ingratiating yourself a little more with his family. And that probably means swallowing your pride and trying to bridge a gap with Rebecca, whom you proclaim to be at the center of the family. I would reach out to her personally — maybe invite her for a coffee — and tell her how much you love Jim, how you would never hurt him, how important it is that you be accepted by his family, and how you would love to start over with her. The worst that will happen is you’ll never have a good relationship with her and she’ll continue to try to “destroy” your relationship. But it sounds as though you’re concerned that your relationship will be destroyed in the long run anyway because you not being accepted by the family, so what do you have to lose?


Follow along on Facebook, and Instagram.

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

27 comments… add one
  • Avatar photo

    GertietheDino October 13, 2017, 8:48 am

    Note: this will not be helpful – Move away and start your own family with Jim (kids, friends, etc.), let those bitches have each other.

    Reply Link
  • wobster109 October 13, 2017, 9:09 am

    My guess was that Rebecca doesn’t want to see Jim grow up or start his own family for some reason. Maybe she’s controlling, or maybe she likes her daughter being at the center. So she prefers Gayle because Gayle isn’t dating Jim. My hypothesis is that if Jim got back together with Gayle, then Rebecca would suddenly prefer you. (And if Jim gets back together with Gayle but Rebecca still hates you, then my guess is wrong.)

    Reply Link
    • LisforLeslie October 13, 2017, 9:44 am

      This is what I was thinking. But understanding the motivation doesn’t really solve the problem. And honestly, I’m stumped. I suppose you could just try to live your lives and keep the sister at arms length until she tires of this game. Is it possible to just try to maintain a relationship with his parents.

      I mean – have you tried killing his parents with kindness? Or just the sister?

      Reply Link
  • Leslie Joan October 13, 2017, 9:15 am

    LW, if you want to be with Jim, be with Jim. I guess I’m not entirely understanding why you are so concerned about the relationship with the rest of his family. There are plenty of cases where people are estranged from the rest of their family, or from individual family members, on account of some pretty toxic dynamics. Sometimes the estrangement is temporary, sometimes it’s intermittent, and sometimes it’s permanent. I guess it just strikes me as a little odd that you are so focused and heartbroken on the wrong thing: he seems very supportive of YOU and of your relationship, and protective of himself to be able to block contact from toxic elements in his life. I’m just wondering if you aren’t stirring the pot yourself, because of the expectations that you have of his family. If they’re all that crazy and dramatic, it’s better to have a distance even if it may cause a certain amount of pain.

    Reply Link
    • Sketchee October 13, 2017, 2:55 pm

      Leslie, I think this is good advice. Jim needs to figure out his family situation. Support him in doing so and otherwise the relationship with him is about the time you two spend together. No one likes to be disliked. And at the same time, it’s okay if people don’t like you. Just be politely unaffected. Focus on your hobbies and life without building it around Jim’s family.

      Reply Link
  • Hannanas October 13, 2017, 9:15 am

    I feel like Wendy’s on to something: this behavior doesn’t make a whole lotta sense without proper context. I mean either they’re both super crazy all of a sudden and only the LW and her boyfriend noticed. Or … the LW has some part in the overall crazy here.

    Reply Link
  • Kate October 13, 2017, 9:25 am

    Gayle and Rebecca put aside their differences and entered into a deal whereby Gayle stole the large sum of money and split it with Rebecca in exchange for Rebecca becoming her advocate with the family, her goal being to get rid of you and reinstate her relationship with your boyfriend. You’re welcome.

    Reply Link
    • Bels October 13, 2017, 10:37 am

      That’s real not a bad theory… You might be onto something

      Reply Link
    • Anonymousse October 13, 2017, 11:10 am

      Ha ha ha.

      Reply Link
  • dinoceros October 13, 2017, 9:27 am

    Two things that stood out to me. I may be wrong, but it seems like you guys went from one extreme to the other in trying to contain Rebecca. You don’t indicate that you tried to do much to distance yourselves from Rebecca up until cutting her off. I may be wrong, though, and if I am, then disregard some of what I’m saying. But I don’t know a lot of people who go to dinner with their partner and one sibling, so it sounds like you guys were trying to have a fairly close friendship with her. Is it possible to create boundaries that are a middle ground between cutting her off and letting her harass you all the time? Did he ever sit Rebecca down and talk about this? Being nice is cool, but it’s not super helpful if you just try to be nice instead of actually communicating about issues. I get that you want an apology, but sitting around and waiting one is not going to resolve things. Can he sit down with her and express his disappointment about their conflict and see if they can work through it?

    I say this because you say you are “quite sure” it may ruin your relationship. I don’t know if this was just vague word choice, but if you think it’s likely that your relationship will end if his family can’t get on board with your relationship, then you need to put your pride aside and try to work it out. Some relationships can handle distance from family, but that’s only if the person whose family it is doesn’t need to be close. I can’t tell if your boyfriend needs that or not. Maybe sit down with him and discuss what your future looks like under various scenarios. (“What if we never make up with her?” etc.)

    Reply Link
  • Boo Berry Waffles October 13, 2017, 10:08 am

    Maybe I missed it, but did you guys ever attempt to sit her down and figure out what the root cause of her approach to you is?

    Everyone’s behavior seems so whip lash, both yours and hers that it lends a lot of credence to Wendy’s assertion that there’s something missing from the narrative. She mentioned edited pieces from the original letter that painted Jim’s sister in a (possibly unjustified) bad light that I wonder if your dealings with her were very judgmental of her and might have spurned on the hostility.

    Nobody’s behavior in this really fits with the facts we’re given, and it all feels kind of off.

    Reply Link
  • Avatar photo

    Dear Wendy October 13, 2017, 11:47 am

    From the LW:

    I’ve just read your reply to my email and wanted to fill some of the details in which you’ve sort of had to guess at.

    I cannot tell you, or understand what it is that made ‘Rebecca’ and ‘Gayle’ close, neither can my partner- which is actually why he feels so hurt and betrayed by his sister. I completely understand why you assume I’ve had a role to play but in total honesty, I didn’t know either the sister or the ex until my partner and I got together, and I actually got on well with the sister until I was on holiday with some girlfriends and I received a call from my partner saying that his sister had asked him to come over, that she was with his ex and she really wanted him to come down, talk to her and try to work things out. When he refused, his ex turned up at his door, begging him to hear her out. This carried on for six months, during which time we tried to talk to his sister about the whole situation so many times, but her answer was always ‘I will not change who I am friends with’. That’s not even what we were asking from her! All we wanted her to do was simply separate her friendship with this woman from her relationship with her brother. After it became crystal clear that wasn’t going to happen, and his ex was going to continue using his sister as an excuse to be present in my partners life, that’s when he ended all contact with his sister.

    I will absolutely hold my hands up and admit now that I cannot stand the sister anymore- I think she’s selfish and manipulative. But at the time I really tried bloody hard with her. Even after the holiday incident, I text her inviting her out with me and my boyfriend, and even a girls night with my friends (thinking that maybe if we became friendly that she would stop pushing his ex back in the picture). The reason I included personal details about her was to show what kind of person she is, and no under normal circumstances I wouldn’t expect family to meddle in a 30 year old woman’s life, but she leans on the whole family so much- and then behaves in such a destructive way that you start to wonder at what point anyone is going to tell her to buck her ideas up.

    As for the strength of our relationship, we are very happy and very much in love but frankly, I’m terrified to lose him to the woman crusading against us that he spent a decade of his life with, who is still involved in his family and lives 5 miles down the road. He has of course assured me that he would never go back to her, but a girl’s self confidence can only stand up against so much.

    There was no affair (actually, she broke up with him the last time), no children etc and that’s exactly why I wrote in. The situation is bizarre, I don’t understand it, or why it even happened in the first place, and I have absolutely no clue how to make it better.

    I am still amicable if I run into the sister, although my partner completely refuses to speak to her. The whole situation has basically been placed on hold for the past 18 months, getting no worse but also getting no better- and yes, the sister and the ex are still friends despite this being the sole cause of the rift in the family.

    Now you know more of the details, as a fresh pair of eyes on the situation, if you still think my partner and I are to blame please tell me because if that’s the case, we probably need to start trying to rebuild some walls.

    Reply Link
    • dinoceros October 13, 2017, 12:52 pm

      Is your boyfriend also questioning whether cutting off contact was the right thing? Because it’s mostly his call here. If he doesn’t want to repair things, then you sort of have to go along with it. It sounds like overall, you’re mostly just afraid that this conflict will cost you your relationship. Nobody here can predict that. If your boyfriend is reassuring you and there’s no indication it’s affecting your relationship, then I think you’re going to just have to trust that.

      Reply Link
    • Leslie Joan October 13, 2017, 6:38 pm

      Sure sounds to me as though Rebecca wants her brother to have a de-stabilized life: she feels a kindred sense of screwed-uppedness with the ex, which is why they get along so well, and why she keeps forcing herself and the ex as a package into Jim’s life. She doesn’t want her brother to be happy, and she’s got a breathtaking lack of boundaries.

      Thing is, Bels, please don’t let this shatter your self confidence. It’s like this: if he actually ever WANTS to go back to her, then you don’t want HIM, because it means he’s as crazy as she is. The fact that he’s cut off contact with them both is a very healthy thing. The rest of the family seems to be in enabling mode; pretty useless, but they don’t know how to manage Rebecca’s craziness and they aren’t going to start. I am sad y’all live so close – this’d be the sort of thing that makes a multistate move look really appealing. But the last thing you want to do is feel any regret for missing out on that toxic family. Sounds as though you two are doing great. Don’t do the man the disservice of doubting him. Stand firmly by his side; that’s what he needs .

      Reply Link
      • Leslie Joan October 13, 2017, 6:54 pm

        Oh, and make no mistake: it’s not that his sister and his ex are friends that’s caused the rift. To describe it that way is playing the crazy toxic hostile sister’s game, because that’s what SHE is saying. The reason that Jim implemented a break is that the two of them were actively and repeatedly shoving their oars in where they had no business being. That would be like a family member kidnapping him repeatedly and taking him to a job they wanted him to go back to after he’d quit. It’s just plain not her business to lobby for another person and to actively interfere with her brother’s relationship. Even if the person she’s lobbying for *didn’t* cheat him out of a bunch of money.

        He understands the magnitude of the violation, and he’s not wrong to be stunned at how venomously fuck-awful her behavior is. I can be friends with someone without interfering in anybody else’s life on their behalf; don’t misunderstand this to be about “friendships”. It’s not her friends, it’s both of their behaviors.

  • Bels October 13, 2017, 11:51 am

    There was no other woman, they had been broken up for months before we even met. As for why she doesn’t like me? Up until the first time she started meddling, I thought we got on pretty well…

    Reply Link
  • saneinca October 13, 2017, 11:53 am

    Why shouldn’t the LW and Jim cut off their relationship with Rebecca ?
    “until the torrent of texts, calls, and visits from Rebecca and Gayle became too much to handle and he blocked both of their numbers and cut Rebecca from his life.”

    Wendy and others have advised people to cutoff relationships with family and friends for far less aggravation than that.

    Reply Link
    • dinoceros October 13, 2017, 12:41 pm

      My assumption was that if they were fine with the impact of cutting Rebecca off, she wouldn’t have felt the need to write in. She stated that she feels like the family conflict may result in their relationship ending, so it sounds like she’s having doubts about it already. I think if her boyfriend is totally cool with the effects on his relationship with his family, then they should go for it. But if he’s not, then it’s going to continue being an issue for them as a couple.

      Reply Link
    • Avatar photo

      Dear Wendy October 13, 2017, 1:01 pm


      Reply Link
  • LisforLeslie October 13, 2017, 12:00 pm

    Thanks for the update LW. Very helpful. Based on this I go back to my original thought which is that the sister simply wants control and doesn’t want her brother to have a separate life. Her behavior is very manipulative and she’s a drama queen.

    I have a relative with a sister in law very much like this. When she was still dating her now-husband the sister was trying to throw a wedge between them and would say awful things about her. Finally the guy told his sister that he was done listening to her nonsense. That it wasn’t acceptable and if she made him choose, he would choose his girlfriend. He had to deal with a number of similar issues over the years as his parents would expect him to put his sister before his wife and he had to very gently but very clearly say “That’s not how this is going to work.”

    Reply Link
  • Anonymousse October 13, 2017, 12:30 pm

    Be kind to his family, even his sister (fake it! Grey rock her crazy antics,) and let HIM deal with his family and crazy sister. He needs to set boundaries and stick with them. Not you. Never you, at this point.

    I don’t mean ‘be a wallflower,’ but he needs to take the lead and work on this, not you.

    Reply Link
    • Vathena October 13, 2017, 1:43 pm

      Yep. Unfortunately, right now it’s his circus and his monkeys.

      Also, I realize you’re frustrated with how his family has backed up Rebecca and her less-than-awesome behavior, but think about it from their point of view too. (Assuming you are talking about Jim and Rebecca’s parents here, mostly?) It’s their child and grandchild you’re talking about. My daughter is only four, but I know I’d put up with a shit-ton of BS from her before I’d ever consider cutting her off, and that goes triple if she has a child. I’m not really sure what you expect the rest of the family to do. It sucks that they don’t seem to be backing up your BF in his entirely reasonable requests of his sister, but it’s a complicated situation for them too.

      Reply Link
  • Ron October 13, 2017, 1:53 pm

    I think Wobrster109 presented the correct explanation toward the start of the thread. Add to that the fact that the ex lies nearby and you don’t, perhaps raising the fear that her brother will move to you. Competing grandkids/nieces is also an issue if brother starts a family, which the on/off nature of relationship with ex says it wasn’t going to happen with her.

    Reply Link
  • Boo Berry Waffles October 13, 2017, 1:56 pm

    Thanks for the update. As with any family dynamics with regards to significant others, I’m an advocate of the people who are actually related dealing with their family and vice versa. That means following his lead on this.

    The good news is Jim seems supportive of you and took this stand in your defense. The bad news is the family will probably blame you for this development, at least for now. I would encourage Jim to maybe reach out to more neutral relative to see about what it would take to defuse this whole situation.

    Reply Link
  • pearl October 13, 2017, 2:08 pm

    I think Wendy is being a bit harsh on the L.W. here. Sometimes,people (like the sister and Gayle) are just assholes. The L.W, sounds like she is sincerely puzzled and has tried many ways to fix this. The sister sounds lik a drama queen,who woul not like anyone-likely including Gayle-who dated her brother. Why,if Gayle stole money from the brother ,wuld the sister support her? Mystery here for sure-but I think it is wrong to put this all on the L.W.

    Reply Link
  • Anonymous October 14, 2017, 10:07 am

    Personally, I think that Jim needs to go see his sister and sit down and have a heart to heart talk with her. He needs to tell her he loves her and wants to have a good relationship and that all this has been hard for him. He needs to tell her he wants to get to the root of the problem. Then he needs to listen. At the end he needs to tell her he hopes she can accept you as part of the family and that it would mean a lot to him if she could. He needs to say nothing about her being friends with Rebecca. If his sister continues to be dramatic about all this, then he needs to let it go. He can just live life and be polite to his sister, but just kind of ignore her. He also needs to communicate better with his parents. (Not you. Him.) He can tell them he really wishes that his sister would accept you and would not be so dramatic and that he wishes to have a good relationship with her. He can tell them that he met with sis and told her this and that he hopes that she will have a good relationship with the both of you from now on. As for you…you should just not dwell on all this or think about it too much. Just stay out of it. (Jim cutting his sister out of his life is a big reason why this has gotten out of hand. His sister’s personality is probably the other reason.) My other advice is: if the drama keeps going on for years you can always choose to live farther away. My brother is on the opposite side of the country. We see each other once or twice a year. We have no part of each other’s life dramas and we just enjoy spending time together when we are together.

    Reply Link
  • Brise October 16, 2017, 3:04 am

    I think you are better off with Rebecca out of the picture. She is just a troublemaker. Don’t make a fuss about it. Your boyfriend was right to stop the pressure. One family rule is, in my opinion: “stand by your family”. In split or divorce situations, unless there has been abuse by one of your folk, you just stick with your own family, not with the ex. To pursue a relationship with the ex is undermining your own parent and is so wrong, as though it is sadder for the family to break up with the ex than for the concerned parent. So your boyfriend was right to cut his sister off for a while if she was off-limits. The problem is now half solved. His family WILL get bored at the end, especially as your relationship deepens. Gayle will get out of the picture, unless she is some kind of psycho, and I don’t think so. She will go on with her life. So will Rebecca. But Rebecca will always be hostile regarding you, in my opinion, because she is jealous. If you marry, she will get jealous of you, jealous of your children, and so on. She is borderline, probably. So my advice would be: just realise it, and accept the idea that you will have to deal with a crazy sister-in-law, and just do damage control. Don’t confront her, always be gracious to her, just know that she is nuts, and as your boyfriend knows it too: that is all right. It won’t prevent you from being happy, you know.
    As for his family: you make a wrong assumption if you think they all side with Rebecca. They can’t ignore her character but she is their daughter/sister/niece. They will want to have a relationship with you if you marry. So be the biggest person and don’t fall into the trap of developing a jealousy with Rebecca. Be graceful, genuine, and don’t make it an “either Rebecca or me” situation. Don’t expect any apology either: it will never come. Keep Rebecca at arms’ length, don’t make the mistake to get too close with her when she will want to reconcile (she is manipulative), and it will be fine.
    Last wrong assumption of yours: don’t think your boyfriend has any interest in Gayle. He doesn’t. Don’t be jealous yourself. Just enjoy the good relationship and go on with your life, your interests, your career.

    Reply Link

Leave a Comment