Dear Amy: My guy and I have been dating for five years, engaged for three, and living together for two.

It’s a second marriage for us both; we are seniors.

Every time I discuss it, he says he’s not ready to set a date, but doesn’t know why. I said I moved in with him because I thought we shared the same long-term goals, and if we don’t, I need to make another plan.

He said, “I will get married to make you happy, but I don’t feel like I’m ready.”

I can easily support myself, and we both contribute to our shared household. It’s his home.

He recently updated his will to bequeath his two homes and a huge amount of money to me. I’m confused. Marriage, more than money, is so important to me.

I don’t understand why he ever asked me to marry him if he doesn’t want to.

I don’t want to force him to get married. His ex-wife cheated on him decades ago and took half of his hard-earned money in the divorce.

I’m going to make one last attempt and ask if a prenuptial agreement would help him feel better about setting a date.

I’m privately in anguish. I also feel humiliated and ashamed with family and friends, because I moved in with marriage as the reason, and now that may not be in the cards for us.

I owe it to myself to resolve this. I could continue to cohabit and wait for when he might be ready, which makes me feel resigned and sad, because it might never happen. Or I could leave, which I don’t want to do.

Do you have any advice for me? I’m lost.

— C

Dear C: You can resolve this only by resolving it for yourself. You cannot resolve this for him.

Your options are stark: You can certainly test to see if a prenup (preserving his assets in case of divorce) will move him closer to a marriage commitment. If he waffles, delays or refuses, and if marriage is a core value and requirement for you, then you can resolve your own anguish by making the very tough choice to exit the relationship.

I understand the embarrassment and possible humiliation you might feel at the failure of this relationship to fulfill your own goals but dragging a reluctant partner over the finish line is hardly the path to the sort of balanced and loving marriage you deserve to have.

This is the kind of important conversation a couples’ counselor could help to facilitate.

Dear Amy: I am the oldest of four siblings. My other siblings live out of state. Our mother passed away many, many years ago. It was just two years ago that her cremains were interred.

We all agreed that we would split the cost of a headstone, with each responsible for 25% of the cost. My sister said she would take care of securing a headstone, but she never did.

Our mom’s 100th birthday is this year. Since this was at a standstill, I took it upon myself to get (and pay for) a headstone.

I sent an email to each of my siblings with a photo of the installed headstone and detailed cost around Mother’s Day.

I offered to be flexible about payment options. I’ve only heard from one sibling. We are all on text/email terms, and I’m wondering how to kindly ask again.

— KK

Dear KK: Wait another couple of weeks. Email your siblings as a group, saying, “I’m circling back around to make sure you all received the email I sent on Mother’s Day. Attached is a photo of the headstone I got for Mom’s grave, along with the cost. So far, I’ve only heard back from Kathy. Let me know if you have any questions about this. I hope we get to see each other in person soon …”

Dear Amy: Thank you for your compassionate response to “Struggling Dude in the Midwest,” the young dad who was so anxious about his stress and the state of his relationships as a result of the pandemic.

This got to me: “Tiptoe out into the world in stages, and you’ll encounter parents of young children and other people (like me) who are also fumbling, blinking and gingerly emerging.”

— Grateful

Dear Grateful: My heart broke for this man. I hope he feels less alone.

Copyright 2021 by Amy Dickinson

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