Family wants to support nephew without condoning behavior

Dear Eric: My adult nephew and his girlfriend recently had a child. They are both in their mid-30s and neither has gainful employment. My nephew has also struggled with mental health issues. His mother passed away several years ago, so his remaining family system consists of grandparents, aunts and uncles.

I am trying to reconcile my feelings of not “punishing” the baby while not “encouraging” the parents’ current pattern of behavior. To this end, I established a 529 college account and will be happy to pay for supplemental experiences for the child, such as camp, classes.

One part of the family says we need to help the baby now, not years from now. How do I get over my anger and frustration at the new parents not demonstrating either basic parenting skills or basic adult behavior?

— Raising a Baby and a Nephew

Dear Raising: Decide if you’re more interested in giving a gift or a lesson. What you’ve offered is generous, but a 529 account can seem like a cold comfort when one is struggling to buy formula or diapers. Ask yourself if helping the family now really “encourages” behavior you don’t agree with or if it is simply standing in the gap for a relative in need.

I’m curious what your relationship with your nephew is like outside of your financial support. Can you offer guidance or advice? What does the rest of the family’s support look like?

Maybe you’re all doing everything you can, to no avail. But attaching strings to your money is just going to cause you more frustration.

Start by accepting that this is where your nephew is right now and recognize that life has dealt him a challenging hand that he’s not playing very well. This may not motivate you to spend more cash up front and that’s fine. But separating your feelings about his actions from the needs of the baby will help everyone.

Dear Eric: One of my closest lifelong friends passed away recently. I’ve been friends with her husband also, since their marriage, where I was a bridesmaid. Their 50th anniversary is coming up next month. I’m heartbroken that “Lou” won’t have his wife, my friend, there to celebrate with him.

Is it appropriate for me to send him an anniversary card? I feel this milestone should be acknowledged in some way, and it might bring him some joy to know I remember. He has a close family and I’m sure their children will acknowledge the date also, but I’d like to acknowledge it myself. We are all grieving.

— Friend in Grief

Dear Friend: I’m so sorry for the loss of your friend. Lou would surely appreciate hearing from you and even be encouraged by the warm memories of that special wedding day. Send a card or even consider giving a call if you feel up to it. You both lost someone who meant a lot to you, so this could be an opportunity for connection and healing, and for sharing happy moments and the hard parts. When we lose loved ones, it helps to know others miss them, too.

Dear Eric: I will be dog-sitting my sister and her husband’s dog in Hawaii when they go away for a 10-day vacation. The husband almost always accuses me of “stealing” something from their home, which I never do because I don’t need anything! He even went as far as accusing me of stealing an heirloom my jeweler grandfather had made and left to me.

The husband sent countless accusatory messages saying that I stole it. He even told me I could have it before he changed his mind about it. The situation lasted for years with no communication from him or my sister.

Should I address this ahead of my visit, telling them that I will not be “stealing” or taking anything because I have no interest in doing so or should I have them go through my luggage before I depart to prove so? Or should I just not mention it?

— Not a Thief