“I’m Jealous of My Boyfriend’s Relationship with His Sister”

I found your website when I Googled about “How to deal with close bother/sister relationships.” My situation is not as creepy as the letter that was posted on your site but nevertheless, I have a similar worry.

I have known my man for near seven years. He has a sister who he is “very fond of” and has indeed said he loves her very very much. The two have a “secret lingo” that they use when they text each other. He has never said a bad word about her and I can see he feels very protective of her and is a little too full of admiration for her.

She is 45 and has never married and has no relationships to talk of. She is a teacher, has a cat, and brings out this alpaca wool teddy bear whose name is a derivative of her brother’s name. I have seen her “feeding” the teddy a biscuit!!! My boyfriend is 46 and has also never been married. I am 46 too and divorced with no children. I feel we’re all a bit dysfunctional but the sister more so. I have extended the hand of friendship twice and wanted to introduce her to my sisters, but this has never happened.

Initially, I was happy that my man related to women well and was close to his sister, but now I get annoyed at the humor they share and that I’m not part of and I can’t appreciate it. They have sickly pet names for each other.

My family loves my boyfriend and he is completely “normal” when with them, but his family has never really been friendly towards me. I accept that they are a more private bunch and I will never be more involved with them and don’t want to be now either. His parents are elderly and he still lives with them but stays with me at my place at weekends. The sister has a place of her own that he visits frequently.

I would dearly love to pool our resources and get a property together, but he always has excuses so I have no choice but to be happy with the amount of time we get with each other and not to push for more. I could end it, but I enjoy his company very much and think it’s only natural that I should want more.

A little over a year ago he told me he didn’t love me anymore and we split up. We had no contact at all, and I picked up the pieces and carried on. I was devastated. Six months later he wrote me a beautiful letter saying he had missed me every day, learned so much about himself lately, and was there any chance I would take him back? I did–and now we are back to the same routine even though I said I would want a bigger commitment on down the line.

Why do you think he has not been able to commit to me completely – and will he ever? — Jealous of His Sister

You have it wrong. It’s not that your “man” is unable to commit to you completely; it’s that he simply doesn’t want to. He likes your current arrangement. For whatever reason, living with his parents works for him. Maybe they take care of him in a way he doesn’t want to give up. Maybe he takes care of them. Maybe spending weekends with you is all the time he cares to be around you. For him, it’s enough. Obviously, it’s enough because, after seven years, he is still resistant to giving you more.

Will that ever change? I have no idea. Probably not. It’s probably better that you accept that this is how it’s always going to be rather than hold out hope that after all these years things are going to change. And once you accept that this is how it’s always going to be, the next step is to decide whether you’re willing to live with how things are for the rest of your relationship. Is this enough for you or are you always going to be nagging him to commit more fully? If that’s the case, you might as well MOA because living with only a fraction of what you want from someone is a miserable way to have a relationship.

As for his sister, I guess I don’t really see what’s so strange about their sibling relationship. Sure, she sounds a bit eccentric what with feeding her alpaca wool teddy bear and all. But other than that, I’m not sure what the issue is. So her brother is “very fond of her.” Why’s that a problem? And he’s never said a bad word about her? The horror!

I don’t know. It sounds like you’re looking for reasons to feel jealous of the sister when the real issue here is that your man doesn’t want the same kind of relationship that you do. This issue is separate from his sister. It doesn’t concern her. It concerns only the two of you. You want one thing and he doesn’t. So decide whether you’re willing to sacrifice what you really want and settle for what he’s offering, or if you’re sick of settling and you’re ready to move on. Those are your options.

After seven years and one long breakup, your boyfriend has made it clear what he’s able to give you. If it’s not enough for you, cut your losses and MOA.


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


  1. You should MOA, to cut to the chase on this one. Is his behavior with the sister totally weird? Well, not totally, but it’s making you uncomfortable, so there is that. Also, the living with the parents thing doesn’t sound like a temporary situation. It is more of a quirk that isn’t going away.

    It sounds like he is nice and that he has some genuine qualities that you enjoy; but it also sounds like these people are strange and not only that but they are really attached to said strangeness. Which is fine for them, but if you want more, go seek it out–with someone who doesn’t have a sister who feeds their Teddy and preferably, someone who doesn’t live with their parents (which, frankly, would be of greater concern to me).

  2. WWS.

    i think this just boils down to the fact that he is unwilling to have the kind of intimacy/closeness he has with his sister/family (not in a weird way) with you. in the “perfect” situation you are thinking of, you would probably get married, im assuming, and with that comes the legal and social implications of you and he becoming each other’s next of kin. he isnt willing to do that. he has, for lack of a better term, ranked you below his family. that isnt necessarily a bad thing, if that works for the two of you, great… but i dont think that is ok with you.

    1. Avatar photo MaterialsGirl says:

      agreed… she’s jealous because to him, his family, especially his sister, comes before his girlfriend. She wants more, obviously, he’s not willing to budge.

  3. Yeah, it feels like this LW is clinging to the close sibling relationship as a scapegoat for the real issue. This guy is happy where he’s at, & that’s not the sister’s fault. He is complacent, doesn’t want a commitment, and has already broken up with you once. I’m sorry LW, but this guy is not going to give you what you’re looking for.

  4. I think Wendy nailed it with this: “It sounds like you’re looking for reasons to feel jealous of the sister when the real issue here is that your man doesn’t want the same kind of relationship that you do.”

    The sister isn’t the issue here, at all. It sounds like you and your boyfriend want different things out of your relationship. You need to have a serious conversation about what you want, and where you want this to go. If you don’t want the same things, it’s probably time to MOA.

    For what it’s worth- my brother and I have all kinds of “secret lingo”. We have inside jokes and stupid sayings, and we get along great. I think he’s one of the best guys I know. My husband isn’t close with his siblings the way my brother and I are, so he doesn’t get it. But he doesn’t resent my brother because of it! He just thinks we’re both nuts 🙂

    1. Yeah, the same thing happens with my brother and I. We both have the same stupid sense of humour, and Arturo lots of the time doesn´t get the jokes. But he has a lot better relationship with my brother than his own sister.

      1. Same thing with me and my brother. We had this inside joke where we kept hiding a spiny pineapple top in each others stuff. I’d find the stupid thing in the weirdest, most random place and then I’d have to outdo my brother by hiding it somewhere equally awesome for him to find it unexpectedly. This went on for like a month and his wife thought we were nuts, but then she started helping us think of places to hide it.

        SWEET! Now I know what to get them for a house warming present… I’m going to gift wrap a pineapple!

      2. haha, my brother and I had a similar joke going with a HIDEOUS doily , but we would dift wrap it and regift back and forth on the holidays and birthdays. Up until my eldest found it, decided she liked it, and kept it hahaha.

  5. Whenever you ask “why” someone is behaving a certain way, the answer is always “because they choose to”. The fact of their behaviour is what you have to address. You are okay with it or you aren’t. It isn’t about you getting him to behave differently. It’s about you making the choices you need to make to make sure you are happy with your life. He is responsible for his choices. His sister has nothing to do with it. And YOU are responsible for your decisions – no one else.

  6. The “boyfriend” has a priority list, and LW is not happy being third, but that’s the way it is.

    One warning, the guy has such a small “world” that he may not do well when his “elderly” parents fade/pass. He may self-destruct, move in with his sister, or appear on LW’s doorstep (no matter what she does now, including moving out of state!).

  7. Talk about burying the lead!

    Sister… secret handshake…biscuits…cats… oh and he dumped me a year ago declaring his lack of love for me and came back six months later, entirely on his terms, and now I’m back to happy time and blaming the sister for the fact that my man doesn’t want a real intimate relationship, and we aren’t on the same page at all. Seems like you are settling LW, MOA!

  8. First of all, when he begged you to take him back you should have laid out your own set of rules for what has to be different this time instead of just saying yes. By agreeing to get back together without talking about what made you unhappy last time, you set yourself up to be unhappy again. Wendy’s right. This isn’t about his sister, although she does sound a bit odd. Anyone who “feeds” an inanimate object beyond their childhood has to be a little off.

    To be honest, it sounds like this man isn’t ready for the things you want like living together and owning property. He’s 46 and has never lived away from his parents; he probably depends on them for certain things and has become so completely codependent now that he can’t fathom moving out. I have a sister like that. She’s the oldest of the 4 “kids” in my family and she’s currently 39. She’s the only one who still lives at home with the parents and has never moved out. She hasn’t dated since high school and expresses no interest in moving out, even though my parents are begging her to. In her childhood, I know that she was severely learning disabled and my parents were worried that she would never be able to live an adult life and learn to do simple things like drive a car or balance a checkbook. Their theory is that she’s afraid to be on her own because everything is harder for her than it is for the rest of us. Maybe something similar is going on with your boyfriend. Whatever the reason though, it seems clear that this arrangement is not working for you so you need to communicate with your boyfriend about the situation. If he really does love you, he’ll work on becoming more independent and setting future goals for the two of you as a couple. If he’s not willing to do that, it’s time to move on.

    1. To your first paragraph, though, she makes it sound like HE was the one who was unhappy and left her – not that she dumped him because she was unhappy and he begged to be taken back. I can see your advice applying if that second situation were the case, but I’m not sure what demands she would have made if she didn’t have problems with the relationship in the first place.

      Second, if the man in question is 45, his parents are likely getting up there in age, probably 60s or 70s – I’d be willing to bet it’s more likely he is taking care of them than that he is so dependent on their support that he can’t fathom moving out. That arrangement is becoming pretty common these days, especially with the costs of retirement and a lot of people losing out hugely on their retirement funds in the recession. I think you may be projecting your sister a little bit on this guy.

      Although I will say, if all of what I said above is true – that he’s a caretaker for his elderly parents – it would be a little weird that she phrased it as “he lives with his parents” not “his parents live with him.” So I could be wrong. But simply living in the same house with one’s parents, even at age 45, does not equal being overly dependent on them.

  9. AliceInDairyland says:

    Ahhhhh, not super related. But WHY did Wendy introduce me to Fab in her newsletter?!?! I have an exam to cram for, and no money to speak of. But I have already wasted 45 minutes on there…….

    PS… WWS.

  10. As Wendy and the others said, it’s not about the sister. Maybe if you guys had a good relationship except for issues with her, but you don’t. He clearly is not willing to give you what you need in the relationship. I don’t know why he’s so weird about his family (have to disagree with Wendy — if the sister was actually playing with the bear and feeding it biscuits, I do find that a little odd for someone her age) or why he won’t commit, but he won’t, it seems.

    1. SweetPeaG says:

      It all depends on the context. There might be some joke that goes along with the bear and she does it (knowing it’s a little nuts) to get a laugh. I have some pretty bizarre inside jokes in my circle.

      But… I lean more towards these people being a little (or a lot) strange. I don’t think the LW would mention the stuffed bear feeding if it was clearly a joke.

  11. WWS for sure. I was reading the letter and trying to connect the relationship with the sister to the out-of-nowhere break-up and then her real question at the end. After reading Wendy’s response I realized, it’s because one has nothing to do with the other!

  12. artsygirl says:

    Anyone else wonder what the parents did that raised two children who are emotionally stunted? The family sounds really interdependent.

    1. Sadly, it must not be that unusual for the area if the LW doesn’t seem to have any red flags about an adult man in his 40s still living with the parents. That’s way more disconcerting that what his sister feeds inadament objects, especially if she’s the one who has managed to get a place of her own!

    2. My hypothesis: they were sheltered too much. My parents tried their hardest to keep me in their little cave and keep me away from all lines of thought that didn’t come from them. It didn’t work on me; I ran away from the insanity in favor of an independent adult life. My sister, however, is exactly like the siblings described here so obviously it worked on her.

      1. the attack says:

        Mine tried that on me too. Now that I’m grown and out of their house my mom is acting a little insane about it. She’s in straight up denial that I don’t live at home with her. She suggested that I keep my medicine at her house and just take a few pills with me because that would be more convenient when she was three hours away from me. She’s always asking my fiancé to quit his really good job and start his own firm in their rural town so we can move in with them…. Uh no. She opens my mail that arrives at her house and then just throws it away saying she’s sure I didn’t want it. I’ve missed bridal showers and other events because of this. I’m so glad I was a rebel and learned independence on my own because she never left my side as a child. Every field trip, every softball practice, every Girl Scout function, every trip to a friend’s house. I was so badly smothered I couldn’t say a sentence without her hearing it. Sorry for the venting session. My brother is in really bad shape from all this too.

      2. Eek, I’m sorry to hear that, theattack. I’ve had issues setting boundaries with my mom too so I can relate at least on that level. Applause for you learning independence despite your mom’s constant presence in your life. Just curious, do you feel this has affected how you interact socially? Are you a more private person now that you have your privacy, or do you thrive more with others around? Again, just curious, you don’t have to divulge if you don’t want to.

      3. theattack says:

        Parents don’t realize that when they “shelter” their kids, they actually drive them to do even crazier things as soon as they get away from you. I went totally insane immediately after graduating high school and did as many drugs as I could get my hands on, having sex with anyone I thought was mildly cute, etc. So the part about learning independence is really scary because teens will do it one dangerous way or another if parents don’t let them have an appropriate amount of control over their lives, ya know?

        I’m definitely a more private person. I can barely stand to be around other people because I’m always afraid of having someone “too much” in my life, so I’m really cautious. It’s also sad because I’m at an age where I want to be able to transition into being friends with my mom, but she’s still so far in denial about me being an adult that we can’t. She gets upset that we’re not close, but I can’t be close to her. Anytime I tell her something she criticizes it and gets too involved.

        Example: Last week my fiance and I went to a wedding a few hours away. We originally planned on going up the night before and making a weekend trip of it. When he got off work that Friday though, we didn’t feel like driving and just decided to go up the next day. No big deal whatsoever. When I talked to my mom on Sunday, I was telling her about our weekend, and she would not let go of why we didn’t stay overnight! She kept suggesting “alternatives” as if it was a problem we were trying to solve presently, and she kept criticizing the decision and basically turned it into accusing me of not wanting to spend time with her (Note that she wasn’t going to the wedding, nor was she anywhere close to it) because in the past I’ve liked to drive up to things the night before but this time I didn’t want to. The fact that we made a different decision which was completely inconsequential meant that I was trying to get away from her and I’m really selfish.

        Another example: I interviewed for a job working with sexually abused children last week. I told her about it, because getting the interview was my first success and I was happy about it! Instead of being happy for me, she uses the opportunity to drill me about why I would want to go into that field and if I was abused as a child. When I told her that was a ridiculous thing to ask, she told me I was avoiding the question.

        How can I be close to someone who acts like that? I really want to have a relationship with her, but it’s impossible to be close when she tries to pretend I’m still six years old. I don’t know if that answered your question, but yes, it’s definitely affected me socially. I’m just lucky that I didn’t let her run over me, which would have been so easy to do.

      4. Wow. I can relate on the “Why can’t you just be happy for me” note – it’s just been recently (like the last year or so) that I’ve learned that I have to carefully tailor how I tell my Mom about things, because the more information I give her, the more ammo she has for questioning/criticism. Just yesterday on my drive to work it suddenly hit me that I can be guilty of doing the same thing – whenever my husband gets a new contract, for example, I immediately jump to looking for faults, complications, or things he may not have thought of. Which is what my mother does to me and it drives me crazy. It was a SHOCKING thing to suddenly become aware of this and I am most definitely going to try to reverse course on that!

      5. Avatar photo theattack says:

        At least you’re catching it now and making an effort to stop! It’s so hard to not slip into habits like that that you’ve seen your whole life.

      6. My mom used to do the same shit. She’s gotten much better when I outright told her to knock her shit off (I’m just a very direct, no-nonsense person). My sister is a very stunted person, and I think that even if my mom hadn’t stunted her, she still would be nuts. She takes after our father, and well, my half-brother is just as incapable of caring for himself as my sister is (from what I hear).

        I finally had to tell my mother that unless she truly wanted the answers to some of her questions, she had better not ask. Luckily, she doesn’t want answers to her questions. She’d rather be in denial (it’s much better for her blood pressure and bad heart).

        For parents like this (it always seems to be the mothers, doesn’t it?), I think that they feel that if the “child” is still dependent on them, then they aren’t “old” yet, therefore, if they aren’t “old”, they are still “youthful”. Youth and the desire to be wanted/needed plays a very fundamental role in the way these individuals operate.

      7. Painted_lady says:

        I think it’s also that a lot of our moms were still of the generation that a woman’s children are the end-all and be-all of her existence. If you’ve been told all your life that this one thing is the most important thing you’ll ever do and that nothing else matters in comparison…I probably wouldn’t be okay with that thing demanding that it live its own life. I think it’s the same way some men get when they aren’t ready to retire.

      8. Wow, are we siblings who have never met? Your mom sounds just like mine. On holidays, if I say I can’t make the 2 hour round trip to their house in between my 11 hour shifts at work because I have to sleep she will honestly suggest that I drive to their house and sleep there instead of home in my own bed. Growing up, I was never allowed to go anywhere except school and church (and work when I turned 15 and got a job just because I was so desperate to get out of the house I would do anything). I’ve been pretty messed up socially my entire life because of this so I totally understand. My middle sister feels the same way and that’s why she was the first to leave home as soon as she turned 18 and has only come back to visit twice since 1999. She moved all the way to Florida.

      9. theattack says:

        That sleep thing is the EXACT sort of thing my mom does! Since I was in an LDR for two years, I would sometimes be driving all over the state, and she would suggest that I drive four hours out of the way to spend the night at her house on Sunday night because it would somehow be more “convenient” than if I drove the shorter distance home.

        I also forgot to say that she thinks she can still tell me how to wear my hair. She thinks my hair needs to be all the way down my back like a little girl, and now that I’m engaged, she keeps bringing up how I need to grow my hair back out for my wedding so I can have it down my back like old times. And it’s not just a suggestion either. She actually gets upset when I get my hair cut to a moderate shoulder length.

      10. Avatar photo GatorGirl says:

        I’m totally growing my hair out for our wedding. I plan on chopping it off the next day , like into a bob haha. I’m doing it for me though, not my mom. She could careless what my hair looked like.

      11. theattack says:

        Haha, More power to you if you want it long! I’ve had long hair my whole life, and I have one of those gowns where the back is open and decorative, so if I had my hair long and down my back it would ruin the dress. Your hair in your profile picture looks long already! Are you trying to get it much longer?

      12. Avatar photo GatorGirl says:

        I’m just letting the mess grow. I don’t have a goal…just long. It’s grown probably another half inch since that picture was taken. The back of my dress is VERY plain so I’m not opposed to my hair covering it. Although I might go with an up do since my long hair is so hot.

      13. theattack says:

        Yeah, the heat is a very good point. Wedding dresses are already so hot anyway there’s no real reason to make them any hotter. I think I’m going to do a loose up-do that hangs kind of around my neck so that it doesn’t give me a headache. Brides are always so uncomfortable. Big heavy dresses, tight uncomfortable hair, high heels. I’m trying to minimize as much of that crap as possible. haha

      14. I did the same thing! I grew my hair out for over year before the wedding (because I wanted to), and then couldn’t wait to cut it afterward. I almost stopped at a Great Clips and cut it on our honeymoon haha. I managed to wait until the week we got back. I’m glad I left it long for the wedding, though. Long hair is how I picture myself, if that makes sense.

    3. kerrycontrary says:

      I know…I really hope I don’t have children who turn out like this.

      1. Avatar photo lemongrass says:

        If you let them have age-appropriate independence then they won’t.

    4. The sister is 45, and the boyfriend is 46. That would lead me to believe they probably grew up very close, maybe with him in a Protector or Caretaker role over her that he still maintains on some level. Also, and I realize this could come across really bad, but the living alone/not-dating/teddy-bear-feeding thing made me think MAYBE she has some sort of mild developmental disability. Not that she’s cuh-razy, but just a little “off.” (I’m really bad about talking about such things in a sensitive way, so I hope I don’t offend anyone with this language.)

  13. You call the sister “dysfunctional”, but the only details you offer about her are that she’s a single cat-owning teacher who really likes her teddy bear. We all do weird shit sometimes, it’s a little strong to call her dysfunctional just based on jokingly feeding it a biscuit once?

    You also say that your boyfriend is “a little too full of admiration for her” but then you admit that “I get annoyed at the humor they share and that I’m not part of and I can’t appreciate it”. It sounds to me like you’re just jealous of the attention that he pays her, and that feeling is exacerbated because you feel like your boyfriend isn’t as committed to you as he should be.

    But really, your boyfriend’s sister probably has nothing to do with your boyfriend’s unwillingness to commit. I think you’re just scapegoating her and their relationship so you have a concrete thing to be mad about, when really, you feel insecure that he dumped you and hasn’t committed to you like you want him to. After 7 years with the guy, and in your 40’s, I think you already should have had multiple conversations being very explicit with your wants regarding commitment. If you want to get married down the line, I hope you’ve told him so.

    As for the sister, I say maintain a positive relationship when you see her, and don’t let your own relationship issues cloud your view of her. You might not have enough in common to be best friends, and that’s ok. And you may never be included as part of her and your boyfriend’s close knit duo, and I think that’s ok too. If you’re lacking for companionship, work on other friendships with people who do want to be your friend.

  14. The LW has been settling – for 7 years! – for a relationship that isn’t meeting her needs. Why? Why are you settling for less than you want? I truly believe that it’s better to be alone than with the wrong person. And what, exactly, would a commitment get you? Do you think that would change everything? He’d still be the same guy with the same family. You’d just have a ring on it.

    I say MOA and open yourself up to finding the love of your life. New romance. New love. Sure, you’d be risking getting your heart broken, but at least you’ll be living your life!

  15. llclarityll says:

    Too many “relationship won’t work” red flags. You sound incredibly immature.

    Side note, anyone think this letter is a fake? The language and structuring of some sentences is odd. i.e. “I would dearly love to pool our resources and get a property together”. Reminds me of the spam emails I get asking me to help get a huge family fortune out of Africa.

    1. I don’t think she’s American. Pretty sure “biscuit” means cookie, too.

    2. Avatar photo bittergaymark says:

      She also found Wendy via google… I assumed the LW was British, too. Biscuits… “Very fond of…” It all sounds decidedly across the pond to me. Not fake, just a bit charmingly foreign…

  16. WWS. The problem isn’t with your bf’s family or his sister. It’s with him. If he wanted more, he would have shown you. All that he’s shown you is that he’s happy with the way things are. It’s not worth waiting around to see if that is going to change at this point. Learn to speak up and assert yourself in your next relationship. If you’re not happy let it be known, and don’t go back expecting things to get better without setting firm guidelines to make sure that the changes happen.

  17. Sisisodapop says:

    So….. say let’s say “my friend” also “feeds inanimate objects”….BUT only when playing tea party / baby dolls with her toddler. Does that still classify “her” as crazy??? (::crossing fingers, hoping I’m not crazy)

    1. Don’t worry there is a little known fine line between crazy…and adorable.

      It also makes my wonder what was happening with the Teddy-bear and biscuit – was it a joke or during a ‘tea party’ – hard to imagine a grown woman out of the blue sharing a cookie with a teddy bear without something else at play…

      1. Maybe she´d forgotten to feed it lunch? I get what you mean though, cookies aren´t the best food for teddy bears. 😉

      2. rangerchic says:

        All the tea party talked reminded me of an episode of Criminal Minds where a grown “woman-child” would kidnap women, paralyze them (but they were still aware), sit them around a table and have a tea party…all because her psychologist father took her doll collection away. So, don’t take away her teddy-bear!

      3. God that episode was freaky-creepy.

        Also, I not supposed to watch that show alone, which I did.

        Creepy. So so creepy.

      4. 🙂

  18. Avatar photo lemongrass says:

    I think the real issue here isn’t that he’s close with his sister- it’s that you would consider buying a property with a man that makes you uncomfortable enough that you would write into an advice column about.

  19. So, I try not to generalize, but in this case:

    “My boyfriend is 46 and has also never been married.”

    “His parents are elderly and he still lives with them…”

    MOA. That is, if “still” means what I think it means, which is “he never left”. MOA. A man who has forced away the social norms of leaving the nest and finding their own life til his almost 50’s is a man who NEVER WILL. And you’re saying the sister is odd?? She’s at least got her own place. Respect.

    No, this dude likes staying with his parents, and unless you’re waiting for a skinny gentleman with a sythe to take care of that parent problem for you (which would be SCARY so please don’t be doing that), I would either be ok with him never committing to you like you need him to, or leaving.

    Ok, actually creepy sister/brother relationship story time: I once dated a younger guy (20, virgin) who still lived with his parents and had an older sister who he was VERY close to. Like, she used to join us on dates and he wouldn’t object. Or, we would be in his room (God, I would NEVER date a younger guy again) trying to get bizzay and his sister would just walk in and sit there. Plus, her personality was THE WORST. She was a blankface.

    Anyway, when we got a little farther into dating, he started telling stories about her and him. Like, sometimes she would ask him to come home when she was going to have a guy come over and then be there with lingerie on, acting surprised that her brother was there. These stories got creepier and creepier and he’s telling them LIKE THEY’RE NORMAL and it was all I could do to keep the 7 days after watching The Ring video expression off my face. SWEET GOD was that creepy.

  20. SweetPeaG says:

    If you don’t want to date a man child, don’t date a man child.

  21. Pant-less drunky says:

    What does the sister have to do with the LW’s question?
    It seems like he’s wants everything his way, he gets a girlfriend without making any sort of effort or compromise and you seem like you just want him to magically want to change for the hell of it even if it makes him unhappy (as selfish or unselfish as that may be). Lay down what you want in the relationship and if you can’t reach some sort of middle ground why bother with him anymore?

    1. Avatar photo lemongrass says:

      Can we be friends?

      1. Pant-less drunky says:

        Of course.

      2. Can we be friends too? Can I call you pant-less for short? I’m dying to know who you are!!

  22. Moneypenny says:

    When I started reading this letter, I was expecting the actual question to be about the sister, not the boyfriend! I have to agree with Wendy though. This guy is way too comfortable with where he is, and at his age, is probably not going to change. Sad to say, but likely true. And he’s getting his cake and eating it too- he gets to stay at the ‘rents (even if he’s taking care of them, he might be getting reduced rent, or other perks), and gets to stay with you, LW when he wants. Sure, his sister may be a little off, but that’s not really the point. He’s too comfortable with where he is as he gets his needs met, and this -may- never change. And there is nothing wrong with you for wanting more! After all of this time, I would definitely want more. You should make your needs clear, and if he can’t or won’t try and make something happen, you should definitely move on and find someone more willing.

    Oh and on the teddy bear topic- I have taken the train (commuter train) with a woman who had a number of teddy bears, and set them all up on the seat and proceeded to talk to them. She even yelled at one to be nicer or else he’d be punished.

  23. Avatar photo bittergaymark says:

    WWS. The sister seems a convenient scapegoat for all that is wrong with your relationship where — lets face it, sweetie, he’s just not THAT into you… He likes you, sure. But not enough to build a real life with you. MOA.

    PS. Oh, and it may be high time to look into getting a cat of your own.

  24. I just want to state for the record, that there is absolutely nothing wrong with having an appropriate caring and loving relationship with your companion pets — dogs, fish, birds — even cats 🙂

    Plenty of animals need good homes, and wouldn’t judge at all feeding treats to teddy bears!!

  25. I am basically of the the opinion of WWS. You are identifying the sister as the problem to avoid confronting the fact that your realtionship with this man is a slow-moving catastrophe.

    In addition, am I the only one who noticed the disconnect between “I would dearly love to pool our resources and get a property together” and “I could end it, but I enjoy his company very much and think it’s only natural that I should want more.”

    You enjoy his company very much, do you? How spiffing. It’s not exactly the best criterion for moving in with him though, is it? In fact, the whole thing appears to be a stealth attempt to create a faux marriage with someone you don’t even love, and as such it’s at least six kinds of pathetic. Plus, of course, it WON’T WORK!

    Repeat to yourself until it sinks in: “HE DOESN’T WANT TO MARRY ME”. You are an accessory to his weird, dysfunctional life, and unless he decides he wants to change that, you can’t alter that situation.

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