Ask Amy: We have talked about marriage, and then he revealed his debt

Dear Amy: I am a divorced mom in my early 30s, with primary custody of my 8-year-old child.

I have been dating “Ben” for the past two years. He is a great guy and he is very good with my son.

We have been talking about getting married. He has never been married before (no kids), and I am gun-shy, to say the least.

I own my home, my son is happy, and I am trying to be extremely careful about our future.

Last week Ben took me out for a drink. He said he had something important to tell me. He confessed that he is almost $20,000 in debt. He said he is trying hard to clear his debt, but he isn’t making much progress.

I have a stable and successful career. I am extremely financially responsible and have already started saving for my son’s college education.

Ben seems underemployed. He is a relaxed, fun person. He said the debt came from purchasing a car and more recently from a ski vacation he went on with some friends.

I feel extremely uncomfortable now. I am wondering if Ben expects me to clear his debt by using some of the equity in my house. He didn’t ask me anything specific and I’m not sure how to feel or how to react to this.

Your wisdom?

– The Responsible One

Dear Responsible: Are you prepared to be a parent to Ben, as well as to your son? Because his choice to lay this on you without a specific plan of action seems to be a bid for you to take this on.

People who have a lot of consumer debt and continue with their spending will sometimes try to get their problem to go away by simply shifting it to someone else.

I suggest that you take this conversation to the next level. Ask for complete transparency and documentation. I think it is somewhat likely that more debt will emerge, once he opens up his books.

Do not marry, commingle your finances or bail him out. He needs to demonstrate a concerted commitment to clear this debt on his own. He is an adult single man with no people to support. He could clear this in under two years, but it would require that he make some big changes.

Dear Amy: My husband and I have a 4-year-old son, and I am pregnant with our second child, due in two months.

Lately our son has been leaving his room and crawling into bed with us. He has done this periodically for the past year, but now it is almost every night.

I have been taking him back to his room, but I am physically pretty uncomfortable getting in and out of bed.

I’m wondering what you think we should do.

– Losing Sleep

Dear Losing Sleep: Leaving their own bed and climbing in with a parent is a fairly common occurrence for children at this age. Sometimes, they don’t even seem quite awake as their homing device leads them to a parent’s bed.

Your son is also experiencing your pregnancy as a child will – with a combination of anxiety and excitement. You can expect him to possibly regress a bit before and after his sibling’s birth.

The most obvious answer is for your husband to take on this nightly task as a way to provide some closeness and comfort for your son while he puts him back to bed.

Otherwise you can do what many parents have done and make a “nest” in your room for him, with a sleeping bag and pillow.

Continue to put him to bed in his own bed, and if he wanders in at night, tell him that mom and dad need their sleep and he can either go back to his room or curl up in his nest until morning.

Also use these last weeks of your pregnancy to snuggle in with some extra closeness with your son. Don’t go overboard with “You’re a big boy now,” but adjust to his needs, answer his questions about your pregnancy, understand that he might be anxious, and offer him lots of reassurance and love.

Dear Amy: “Distant Grandpa” is trying to build a relationship with his granddaughter, who lives across the country.

I resented that you described him as “a nice old man she doesn’t know very well.” He is her grandfather!

– Upset Grandmother

Dear Upset: “Grandfather” is a role this man needs to grow into. So far, he’s not doing a very good job.

You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.