I am the youngest of three siblings and no longer close with either of them. My eldest sister has a severe drinking problem and is always looking for her next drink. My older brother is an “entrepreneur” in constant search of his big discovery. He’s 65, she’s 62 and I just turned 60.

Neither of them wished me a happy birthday or tried to do anything special with me, let alone get me a gift. They completely ignored and/or forgot. The next day, my sister was at my door, “sweetly” asking if I had any rum because she was “baking a cake” for her boyfriend.

She doesn’t bake. She doesn’t cook. She’s a drunk.

The following day, my brother called to ask if I wanted to invest in a new product he was hoping to bring to Canada – side saddle bags for dogs to carry their own items to the beach. We live in a suburb of Toronto, an hour from any beach!

I want to excommunicate myself from my family, but I know it would break my mother’s heart. The saddest part of all is that my parents are constantly giving my sister whatever alcohol is in their house and investing in whatever garbage my brother is working on. They have remortgaged their house twice!

I have told them to stop buying any alcohol whatsoever, so that when my sister comes over, they literally have nothing to give her. And I’ve told both them and my brother to stop giving him money for all his unsuccessful ideas.

How can I extricate myself from this mess?

Last man Standing

I was unsure how to respond to this question, so I conferred with a lawyer. Since your parents are elderly, what your brother is doing can be considered abusive. However, if your parents are of sound mind, then they aren’t being coerced, so much as acting how many parents would, believing in their children and wanting to help them out any way they can.

However, if you’re noticing some decreased capacity, which wouldn’t be surprising at their age, you could request they have an assessment done, which could then prove that your siblings are putting them under undue influence, and you could request a financial guardian be put in place, so your siblings don’t completely bankrupt them.

It would behoove you to discuss their power of attorney plans. You won’t be creating any sibling harmony by insisting you take over both, but from your description, neither of your siblings should have control over either.

If you walk away, your worst fears could come to pass, so decide what you’re capable of handling.

I’ve recently started dating a young widow, whose husband was almost two decades older than her. Financially, he took care of her, even though she has a very good job. He was also from another era of chivalry and romance. I’m worried that her expectations are too high and that I’m competing with a ghost.

I really like this woman and would love to see if we have a chance. What should I do?

Not old enough

Stop competing and just be yourself. Is she going to compare you to her deceased husband? Yes, of course, because she loved him and he was a good husband. And it sounds as though he set the bar high. None of that should be a deterrent to you.

She obviously likes you if she’s been on a few dates with you, so just be yourself. You could learn from his example without becoming a replica. And she may enjoy the fresh, younger version of a partner after years of being with someone much older and seemingly more traditional.

Give it time.

FEEDBACK Regarding MAID (July 2):

Reader – “It’s not YOUR life and therefore NOT your choice.  As an adult, she has agency over her life and her decisions whether you agree or not. By acting like it’s you who were inconvenienced – you’re not thinking of her; just wanting to exert your own control and power over someone else’s life.

“How is this loving or supportive?  It’s hard to let go of someone you love, and hard to live without someone – but this isn’t a choice you get to make for someone else. You have no right to stand in the way of others if it’s their legal choice or to second guess their definition of quality of life.

“MAID exists so that people may make their own choice about how they live their lives and how they choose to exit.  Personal agency is always critical but especially when one is facing a significant health issue.”