Difficult Sister

I would really appreciate some advice about how to deal with my older sister. She is 53 (I’m 46) and went through her 2nd divorce 3 years ago, ending a fairly turbulent relationship with a narcissistic man. Since then she has been seeing various men from the Internet and usually sleeping with them. She has also been on a TV dating show where she got drunk. One of her Internet dates was a man who has had previous convictions for stalking. He writes a blog and in it he has talked about my sister and given lots of details about their sex life. My sister has broken off with him numerous times but always ends up getting back with him. I believe she enjoys the drama of it. She has now told me she is going to pursue a relationship with him even though she doesn’t like him. All her 3 children think he is a total creep. He has told her he thinks her youngest son (13) is a despicable human being. I am worn out with the emotion of it all. We have always been very close and I am finding it hard to work out how I can continue a relationship with her when she is seeing this awful man. I can’t support the relationship, but I don’t want to lose my sister.


If you have to choose it will be a losing battle. Your sibling is technically a mature adult but she seems far keener on dancing with her demons than destroying them. She’s not alone; as we get older plenty of us find it so much easier to live with the devil we know. Contrary to popular assumptions that tends not to be our partner but ourselves! Further entrenching our dysfunctional tendencies rather than trying to evolve beyond them is the easy option and it’s a route we naturally lean toward. Grumpy old men and women have become a stereotype because so many of us allow the accruing of experience to lower our tolerance rather than open our eyes. Indulging your worst instincts is like slipping into old shoes; they may lack support and accentuate bad habits but they feel so right!

Your sister is on a romantic path that will bring her only woe but it’s what comes naturally. She seems to have a serious problem with her sense of her own value. Exposing herself through her lover’s blog and humiliating herself in public are not signs of a healthy state of mind. She seems to have a problem with self-value. I fear that telling her that she is making mistakes might be more destructive than constructive as she lacks the self-awareness right now to see a bigger picture. A good reason for refraining from further judgment but hovering in the background is to keep an eye on your nephew. Pursuing a relationship with a man who appears to have little regard for her privacy or her children’s wellbeing suggests she’s capable of being truly reckless.

You are a few years younger than your sister and won’t yet know how profoundly reaching the fifty mark can impact on a woman’s mental health and sense of self-worth. I would definitely advise a trip to a sympathetic GP as there might well be medication that can help build her confidence about herself. There’s a vast ocean of negativity around mature womanhood but many negative traits stem from physical causes that can be attributed to turbulent hormones rather than wilful bad behaviour. You suggest this particular stream of irresponsible indulgence is a recent thing and I suspect a health check might prove more productive than trying to analyse her behaviour. So much is being discovered about the impact of hormone loss at this transformative time and many women fail to get the help they need or are embarrassed to ask.

All that notwithstanding, having just emerged from “the season to be jolly” I bet there’s plenty of readers out there who are sick to death of family members. Your sister does sound like she’s failed to mature into adult relationships and is behaving pretty irresponsibly as a parent. Wasting your time on narcissistic, attention seeking, unreliable and untrustworthy men is bad enough in your twenties when you have time on your side and naiveté to excuse you. Three decades on and two divorces down the line she really needs to wake up to the futility of the endlessly repeated mistake.

Life needs some form of forward momentum or it becomes barely livable; whether that comes through working on your personal foibles, raising another generation or finding continuing challenges to inspire you doesn’t matter, but stuck in a groove is a form of early retirement. Altering the behaviour of those close to us is almost as tough a challenge as changing ourselves and you don’t want to make it your personal vocation. It sounds like you’ve been a pretty good sister to date, there when she needs you and prepared to stick with her. I’d try talking about physical health rather than emotional issues and encourage positive action with a trip to the doctor. I’m sure that if your sister was feeling strong, well and confident she’d wake up to her foolishness on the romantic front. New Year is a popular time to resolve to make changes and there are few among us who wouldn’t benefit from a little fine-tuning. Your sister is in good company!