Years Later, Divorce Leaves Doubt About Remarriage

Dear Sugar Radio is a weekly podcast from member station WBUR. Hosts Steve Almond and Cheryl Strayed offer "radical empathy" and advice on everything from relationships and parenthood to dealing with drug problems or anxiety.

Today the Sugars hear from a man in doubt. He says he's found an "incredible woman" and the two of them "match up splendidly." He wants to propose to her, but an earlier experience with divorce has left him hesitant to remarry. How long should people date before getting engaged?

Dear Sugars,

I have found the most incredible woman. She's smart, beautiful, warm, caring and my friends and family think she's fantastic. We haven't been dating all that long, so I'm not going to rush into anything — it's too soon. But we see eye-to-eye on everything, we've had some pretty significant talks — things like where we'd like to live, views on life, money, work, relationships, sex, etc. Big conversations. All the major items on our respective checklists are sorted. We match up splendidly, and I cherish our time together.

Here's the issue: I'm divorced. I broke up with my ex four years ago, and I've learned a lot since then about myself, about relationships and especially about life. At 35, I've finally had healthy relationships, and I've found forgiveness for my ex. I feel ready to be married again. But the question that lurks at the back of my mind is, "How do I really know?" Divorce was the worst thing I've ever experienced, even though I'm the one who initiated it. There's no way I want to do that again. I rushed into marriage the first time, I see now. But when it comes to doing it again, I don't want to wait forever.

My girlfriend and I have plans to take a trip to Europe later this year. I see that as the perfect time to ask her to marry me. At that point, we won't have been together a year yet, but it'll be getting close. Is that long enough? Why am I worried about if it's seen as long enough? Am I worried that others think I'm rushing into it again? My best friend is the only one I've told that I could see myself marrying her. He can be brutal when it comes to analyzing relationships, and he's been right about every one I've been in — including my former wife. He didn't flinch when I told him I thought she was it. He said he'd be happy to see it.

Lend me your insight, Sugars.

Signed,

Help Me Be Ready

Cheryl Strayed: Help Me Be Ready, when people ask us a question, it often arises because they're asking themselves. You are feeling doubt about doing this. I say, trust that. I don't think you need to wait terribly much longer, but a European vacation is not the only cool place you can propose. Why not give it a few more months to quell the doubt that you seem to have?

That's my advice to you. And then do it. You know what's in your heart. You know that marriage is never a guarantee. You know that you could get married again and divorced, as much as you don't want to do that. And you need to enter into it embracing that sense of doubt and uncertainty.

Steve Almond: Help Me Be Ready, you said you've had talks, the big conversations, about life and money and work and relationships and sex — everything. And I say, but not about marriage and divorce and children. Have you had those discussions and told your partner, "I really feel good about this, but I also have been bitten, so I'm twice shy"?

Have you thought about the events that led to your divorce and whether there are similarities or distinct differences in how you've conducted yourself in this relationship? If you have doubt, it's not coming from nowhere. You need to have big conversations with this woman that you love so much.

Cheryl: You asked, "How do you really know?" What I've come to understand in my own life is, you can know what's true in a moment in your life but also know that those truths will change over time. Listen to the doubt that compelled you to write to us. That doesn't mean you won't marry this woman someday. It just means, listen to those doubts. We wish you all kinds of love and luck in this relationship.

You can get more advice from the Sugars each week on Dear Sugar Radio from WBUR. Listen to the full episode to hear more from people doubting their relationships.

Have a question for the Sugars? Email dearsugarradio@gmail.com and it may be answered on a future episode.

You can also listen to Dear Sugar Radio on iTunes, Stitcher or your favorite podcast app.

Copyright 2017 WBUR. To see more, visit WBUR.