Help! I Just Discovered My Boyfriend and I Got Divorced for the Same Reason. Oh No.

Dear Prudence is Slate’s advice column. Submit questions here. (It’s anonymous!)

Dear Prudence,

I’m a 50-year-old woman. My boyfriend George and I have been dating casually for over two years and became exclusive at the beginning of this year. When we met, we knew we were both divorced and not looking for a serious commitment. We also didn’t disclose the reasons for our divorce, which was fine with me. The only information we knew was that both our divorces turned into an ugly mess. Three weeks ago, I attended the wedding of George’s son. I was warned ahead of time that George’s ex-wife Linda would be difficult and might be resentful of my presence. As predicted, Linda made a scene at the reception. After she was escorted away, George’s sister Melissa went to check up on me. We got to talking, and I pressed Melissa to reveal the reason for George’s divorce.

Linda had persuaded George to have an open marriage, and after being unhappy with the arrangement, they divorced. The revelation hit close to home for me, as that was what I did to my ex-husband. All of the guilt and remorse I felt in the months leading up to and after my own crumbled marriage resurfaced, and I saw myself in Linda. Like Linda, I too was viewed as a pariah by my own children and relatives. I’ve long regretted the choice I made and the hurt I caused my ex-husband and my children. It has taken me years to turn a corner and build back my relationship with my children. I’ve continually feared having to explain to any of my future partners the full details of my divorce. I had hoped after a few years of being together, I would feel comfortable enough to tell George the whole truth. Never in a million years did I think I would meet another man who went through the same struggles as my ex-husband. George is a sweet and loving man whom I feel comfortable moving forward in my life with. My heart would be broken for a second time if things were to end between us. I fear that once George learns about this part of my past he’ll end what we’ve just started. I’m not that woman anymore, and the reasons I wanted an open marriage were no longer important to me. Should I tell George the truth? I worry he will eventually find out. I’ve intentionally tried to limit George from any contact with my family. But my own children’s wedding days will be coming soon, and an easy slip-up could just as well happen. Should I confess my past deeds?

—Opened Past

Dear Opened Past,

You have to tell him. “I got divorced because I wanted an open marriage” would probably be hard for George to hear, but “I got divorced because I wanted an open marriage, and I completely regret it. I’m not the same woman anymore and have no interest in that kind of lifestyle these days. I know this is probably a sensitive issue for you because of your history, so I hesitated to bring it up, but I didn’t want to hide anything from you” will be a lot easier to digest. Or at least, it should be.

Keep in mind, this is not the same as you dropping this on him on the second date. He knows you. He loves you. He’s serious about you (enough to bring you to a wedding and risk the resulting drama!). If your connection is as strong as it seems to be and if he’s reasonable, I think that this conversation can happen without any major repercussions. You have to tell him because if you don’t, the secret (which, by the way, isn’t anything to be ashamed of) and the fear of what happens if it’s revealed will take a real toll on your ability to enjoy the relationship.

Dear Prudence,

I am a cis female in my early 30s married to an incredible partner (cis man in his early 40s). We have been married for about a year and a half and both want children. However, I am hesitant to start trying because we haven’t had a dream, tropical honeymoon yet. We both brought some financial debt into the marriage (his debt was about twice as much as mine). Following our wedding, we opted for a local getaway at a bed-and-breakfast, with plans to one day do a big vacation in the future when we could afford it. Since getting married, we have worked hard to save and pay off our debt—and I’m proud of the progress we have made so far!

Now that becoming debt-free is on the horizon, discussions about what’s next for us have begun. I want to save up to finally go on our honeymoon—but he wants to start having kids ASAP. We both want a family, but my husband is more anxious to hurry up and get started on that because he has concerns about being an “old dad.” Meanwhile, I feel like if we don’t take our belated honeymoon before we get pregnant, we never will! I’m worried if that happens, I will end up silently resenting my partner and even worse, my future child! Of course, we could always go on vacation after becoming parents and leave our child with family (his parents or mine), but I feel as if the experience would be more enjoyable before having a kid, without having to stress about being separated from our child. I have voiced these concerns to my partner, and while he appreciates and understands my perspective, he still feels pretty strongly about prioritizing our family planning over our dream honeymoon. Am I being totally irrational, selfish, and silly about this?

—Paradise or Pregnancy?

Dear Paradise or Pregnancy,

No, you’re not irrational, selfish, or silly. You both have valid concerns but if you have to break a tie between the concerns of a person who is not going to have to physically carry a baby and deal with all the changes and challenges that come with that and a person who is not, I think the person who’s going to carry the baby should get to win. Of course, insisting on winning isn’t a great way to have a happy or healthy relationship so my telling you, “You’re right and he’s wrong” won’t help anything long-term. But it could give you some good information.

I completely support you refusing to get pregnant until you feel ready to be pregnant—whether that’s physically, emotionally, or in terms of the items and experiences you’ve checked off your child-free bucket list. And until you feel ready, you should observe your husband. If he shares his stress about becoming an old dad, suggests a compromise (like taking the honeymoon in six months rather than a year), or asks to work an expensive gym membership into your household budget so that he can get into better shape and feel less angst over his age, fine. But if sulks his way through the honeymoon, boycotts it because it wasn’t what he wanted, or continues to insist that you should have a baby before you want to, you’ll really want to give some thought to whether that’s someone you want to deepen your commitment to by having a child together.

Submit your questions anonymously here. (Questions may be edited for publication.) 

Dear Prudence,

My brother is a 38-year-old, heterosexual male who has never dated. He is very private so trying to discuss this in person is difficult. He is discouraged or too shy to put himself out there. He has so many wonderful traits—he’s a helpful friend, takes care of our aging parents, and is great with kids, handy around the house, athletic, and in great shape! However, he is on the shorter side and works a less glamorous blue-collar job so some of the superficial filters women tend to use on dating sites would overlook him. I am sad to think he might miss out on finding a life partner or becoming a father. He would be an absolute steal for a single mom looking to date! I would like to send a genuine offer to help via email (less confrontational). What advice would you give him?

—Hopeful Sister

Dear Hopeful Sister,

Your brother sounds great and your love for him comes through in this letter. But I have to be honest and say, that shy, short blue-collar men everywhere are in relationships and married. So while I’m sure the things you mention aren’t helpful when it comes to having success on the apps, I think there’s more going on here, especially if he has never dated in his entire life. What exactly, I don’t know. Maybe he’s asexual. Maybe he’s one of those men who thinks he has to reach certain milestones before he can meet a partner and provide for a family. Maybe his priority is taking care of your parents and he knows he doesn’t have the time nurturing a relationship would require. Maybe he’s in a relationship—or has been in a series of relationships—that he’s elected to keep secret for some reason. Maybe he thinks the apps seem stressful and is willing to hold out for an organic, in-person “meet cute,” even if it doesn’t come until he’s much older. Maybe he thinks being married with kids sounds absolutely awful!

So I don’t think you should offer to help or send him your advice. That’s because even if none of the scenarios I’ve imagined are accurate, and he really would actually like to have a partner, dating is hard. It takes a lot of stamina and resilience. I worry that someone who isn’t motivated enough to drive the process himself isn’t going to be equipped for the inevitable roadblocks and disappointments. Imagine you email him saying, “If you want to find a girlfriend, one good place to go would be a wine bar. There are always groups of single women there,” and he takes your advice and goes. What happens if he’s rejected when he asks for someone’s number or if he goes on two dates and gets ghosted? Now you’ve set him up for disappointment, and will probably feel the need to give more tips—on personal grooming, on how to flirt, on the right way to send a text. If it does work out and he connects to that amazing single mom, you’ll have to watch him stumble through the growing pains of his first-ever romantic relationship and all the mistakes and misunderstandings that come with that. And you’ll be in way too deep, tempted to send another email full of advice every week.

Of course, if he ever asks you to set him up or for general help, jump right in. I don’t mind if you want to keep a list of single friends who you think might like him, so you’re ready to set up a date if you’re called into action. But until then, the best thing for you to do is to make sure he knows how great you think he is—just as he is now, without a wife and kids—and continue to be a supportive sibling. Romantic love is great for people who want it, but it’s not the only kind of love out there and it’s not the only path to a happy life. The relationship your brother has with you and your parents is something to celebrate, not just something to settle for until the right woman comes along.

My husband and I have been married for three years. We have a 4-year-old son and 16-month-old twins. I have four older children. My husband was briefly married once before me; I was previously married for 12 years. We were both going through our divorces around the same time, messed around, and got pregnant. We hadn’t planned on anything serious, but we gave it a shot and ended up falling in love. Early in our relationship, I shared something vulnerable with him: I got pregnant with my oldest at 16, and I never told her birth father.