Life Advice



Sister Is Dating a Felon

Annie Lane on

Dear Annie: My mother died at the age of 67 from COVID-19 in January. My stepfather wanted to wait a year to have the memorial so everyone could attend. Since my mother's death, my stepfather has remarried. Yup, remarried. And now his new wife has moved into the house.

My stepfather is now saying everything in the house is his and is being resistant about allowing me or my brothers into the house to get my mother's belongings that are sentimental to us. My mom, unfortunately, did not have a will. What do we do? -- Remarried after Death

Dear Remarried: First, I'm so very sorry for the loss of your mother. Sixty-seven is too young, and I'm sure you miss her every day. Try to be happy that your stepfather has found another companion; everybody grieves at their own pace.

Inheritance laws vary state by state, so the best thing you can do is consult a lawyer. I would give your stepfather the heads-up that you are doing this; it might persuade him to let you into the house and take items of sentimental value before getting lawyers involved.

And remember: No matter who lives in that house, no one will ever replace your mother.

Dear Annie: My sister has recently become involved with an old high school boyfriend. Our family had issues with him 30 years ago. He now lives across the country from her. Recently, she went out to visit with him for a week, and she took her 21-year-old daughter and daughter's boyfriend with her.

We did some checking before she left. He was convicted of rape and assault about 10 years ago and served five years of a 16-year sentence. I confronted her, and she says she has known about it for years. I found some jailhouse letters from him when I cleaned her car.

She has a 21-year-old daughter and a 16-year-old daughter. They both feel that if he makes her happy, so be it. They both know about his criminal record.


The family has told her he will not be allowed around any of us for any family events. She is hinting he might move around here. She is hoping for a long-term relationship with him. She has no self-confidence. She's shy. She says he's a changed man and that he was set up and drunk when the crimes were committed. We are really worried about this. He has abused other women, according to trial records. Help. -- Terrified for Sister's Safety

Dear Terrified: Your concerns are valid. Regardless of whether he was "set up" or "drunk," he is a convicted criminal with a history of violence against women. This, combined with your family's disapproval of him 30 years ago, is evidence enough that the man he used to be is not worthy of welcoming into your family.

And from your letter, it sounds like he's not much better today. The fact that he's giving your sister excuses shows he hasn't owned up to the pain he's caused. A second chance is already a big ask, and your sister shouldn't even consider it unless he takes accountability and proves he's taking steps to becoming a new, better man.

You can also explain to your sister that dating a felon could jeopardize the custody she has of her 16-year-old daughter, assuming the father is still in the picture.

Remember, forgiveness is one of the most powerful gifts we can offer -- but it would be foolish to give it to someone who hasn't earned it.


"Ask Me Anything: A Year of Advice From Dear Annie" is out now! Annie Lane's debut book -- featuring favorite columns on love, friendship, family and etiquette -- is available as a paperback and e-book. Visit for more information. Send your questions for Annie Lane to




A.F. Branco Brian Duffy Barney & Clyde Brilliant Mind of Edison Lee Tim Campbell Nate Beeler