My son was a principal partner in a start-up business and after ten years of very hard work, had the great fortune of being bought out. His share was in the millions.

Meanwhile, his sister’s struggling financially. She made some bad decisions with her education and her choice of partner, and is now a single mom whom I help support. She works part-time.

When my son got his buy-out, he gave us both a one-time gift of money. She bought a car with hers; I put mine into a fund towards her daughter’s higher education. But I worry about their future.

I’m 65, and pretty healthy still. I believe in leaving equal shares of whatever I have at the time of my death, to each child, but wonder if, in these circumstances, if I can leave it all to my daughter without offending and hurting my son?

Planning My Will

You may yet live a long life, so whatever you decide, make sure you’re putting aside money for your own care and comfort, as you grow older.

Get legal advice regarding what you consider as complications.

Then, talk to your son. He’s aware of the difference in his sibling’s circumstances… but he’s not responsible for them, so don’t impose guilt.

Ask his financial advice as to how you can best try to help her now, and how he thinks you should structure your will to help her later. He may even suggest that he requires no legacy, or that he’ll “look after” his sister (not for you to suggest).

BUT, remember – he’s a self-made man, whose decisions and labour paid off. Your daughter won’t develop the drive and determination she needs for the future when you’re gone if you set up too many cushions for her to lean on now.

Do what you believe is necessary for your grandchild, but encourage your daughter’s own efforts with a hand up – towards upgrading courses, self-esteem boosters, etc. - not just handouts.

FEEDBACK Regarding the aunt who’s outraged about neglect of her developmentally-delayed niece (March 28):

Reader – “Your brother-in-law and his wife are now allowing the school psychologist to see the girl. The parents were in denial before, this is a difficult journey for them - respect their journey.

“Forget nutrition for now. Feeding kids often becomes an area of conflict in families - it's something people easily try to control.

“Developmental issues are more important, but more elusive for families to deal with. Good nutrition may come later, if and when parents accept their child’s developmental needs.

“Build your relationship with the parents and get on "their side." This takes time and a lot of listening and being quiet (by you).

“Be helpful, like hosting family gatherings or organizing kids’ activities at a gathering. Spend time with their child (but ask parents’ permission first to show you know they’re in charge of their child).

“Even if the parents get a diagnosis, they may never admit this to you because of anger from your past conflict-based relationship. Accept this. Be content if their child is getting help. Be a support without asking what the diagnosis is.

“If you see lack of movement toward getting help, share with the parents stories about kids you know or heard about, with good outcomes, highlighting areas you know will be of interest to them. Keep the good stories coming.

“If parents continue to be stuck in denial, the school most likely will involve children's services if needed.”

My best friend knows this guy at her school. He hasn't had a happy past year so she became friends with him. I've met him, we started talking and she thinks he’s using me for attention.

I don't want to upset her or her relationship with him. I don't want to choose between her and this guy.

He's a nice person and seems intriguing. I don't want to be mean by ignoring him… or do the opposite of what my best friend thinks I shouldn't do.

Friendship Triangle

You’re talking yourself into this friendship. You already know the BFF rules: If she likes the guy – which is likely since she’s giving you reasons for you to re-think getting closer to him – then he’s no-go territory for you.

Your use of “intriguing” is the clue that you’re starting to get interested and playing with fire with regard to her feelings. Back off.