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Dear Prudence,

My husband and I are approaching our one‑year anniversary, and I’m questioning whether he is equally invested in our marriage. We met when I was 31 and he was 54. He is my first partner, while he has had many relationships and has six adult sons. Early on, we discussed boundaries with his exes, but those boundaries haven’t been respected.

A couple of months into dating, his youngest son’s mother called him before he was headed off to work and he acted very weird about it. When I asked about it, he said she ONLY calls their 29-year‑old son, not him, which clearly wasn’t true. He then told me, “She’s not going anywhere—she’ll be here whether I’m with you or not.” I didn’t know how to respond.

Two days after our wedding, he acted single at a family birthday outing—pointing out women he’d pursue if he weren’t with me and focusing on one woman most of the night. When I confronted him, he said he didn’t want to go because those environments “bring him back to his old ways,” then he tried to reassure me by comparing my looks to other women in a way that felt hurtful. Since then, he avoids date nights and social events, saying restaurants, clubs, and even funeral repasts are “too much temptation.” He says this is why he can’t spend time with me in those settings and that we “just need time to get to know each other over time.”

He also told me he had no contact with exes, but they’ve all resurfaced at different points. He has compared my lack of sexual experience to his exes and bragged about how they pleased him. He refuses to communicate about intimacy, saying the other women “just knew,” and I should figure it out myself.

More recently (and unbeknownst to me), he arranged for me to meet with his youngest son’s mother, and she reached out to tell me things he has supposedly said about me. His family and friends have hinted that he may still have feelings for her, though he denies it. She told me she doesn’t want him, but expressed concern that he may have ulterior motives for being with me. When I brought these concerns to him, he focused on being angry that I “listened to her,” rather than addressing or clarifying anything she said.

I’m struggling to understand what the hell I got myself into, and I’m confused on the steps I should take to rectify or end this.

—Broken Hearted Girl

Dear Broken Hearted,

You asked for the steps you should take, so here they are:

First step: Think of three people (probably women) who you respect. They should be friends who, whether they’re married or single, seem happy and stable. They don’t have to have perfect lives, but they should not be stuck in relationships, jobs, friendships or troubled family situations that cause them ongoing angst.

Second step: Ask them all to meet up with you for a meal or coffee or drinks or a walk.

Third step: Let them know that they’ve been appointed to your personal board of directors and you need their guidance.

Fourth step: Tell them everything you told me in this letter.

Fifth step: Say “I’m asking for your honest advice. Should I try to rectify things or should I end this marriage?”

Here’s a big spoiler: They’re going to tell you to get out. That’s because if you remove the uncertainty that comes with being in a first relationship, and the feelings that made you want to marry this guy in the first place, it’s undeniable that he’s offering you nothing but disrespect, confusion, and pain. Also, at the risk of shaming him for having many decades worth of romantic entanglements, he has a pretty significant history of failed serious relationships and doesn’t seem to have learned many lessons. Most obviously, you’re unhappy.

You see that I’m not diving into the details of the exes and the phone weirdness and the bizarre avoidance of social events. You’ll unpack all of these things over the prescribed gathering with your wise friends, but the specifics don’t even matter that much. The bottom line, which I feel confident people who care about you will pick up on, is that this older man targeted you as someone who would put up with his antics (which, if they aren’t emotional abuse, are too close to it for comfort) and has proceeded to be the worst spouse imaginable. You need real people in your real life to confirm that. You need them to rebut whatever arguments you make about how he said he will change, or about how you’re worried you won’t find someone else, or whatever other thoughts you have that might lead to you wasting your life with a person who offers no benefits at all over being single.

Dear Prudence,

I am in love with someone, but I don’t know what to say. He seems like he thinks positively of me, but it’s complicated. I just don’t know whether to stay quiet or do something.

—Lapis Lazuli

Dear Lazuli,

“He seems like he thinks positively of me” is a little underwhelming. Your colleagues at work might think positively of you. The person who works at the gas station shop where you fill up your car might think positively of you. Any number of individuals who perceive you as responsible or kind or nicely put together might think positively of you. Most of them would also be fine if they never saw you again. So it’s a very low standard. Unless you have reason to believe that your crush is so shy or unexpressive that he wouldn’t offer any real indication of his love, I don’t think your feelings are reciprocated. I’m sorry.

If the object of your affection is a casual acquaintance, stay quiet. There’s no need to open up and get rejected. But if he’s a good friend, you should fess up. A friendship in which one person secretly pines for the other and privately wants more is never going to be really authentic. And this dynamic will probably lead to you acting weird at some point. So for the sake of being honest (and the small, small chance that hearing about your feelings will activate him and you two will live happily ever after), come clean.

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Dear Prudence,

My wife loses everything! Phone, keys, wallet, chargers, papers, rings, water bottles, bags, shoes, other articles of clothing, sentimental gifts, you name it. She even loses digital items. I am completely the opposite. I almost always know where everything is, physically and digitally. I even have all my emails neatly organized by folders. When we were dating, I found this rather cute, and I loved helping her find her missing things. But I can’t take it anymore! I’m also worried about what this would look like with kids and the implications of losing their things, as we want to have children in the near future.

How can I help her keep track of items? We put AirTags in her wallet and on her keys, but we can’t AirTag everything she has. She’s medicated for ADHD, and while it helps in a lot of areas, this isn’t one of them. Any advice would be appreciated!

—Sick of Scavenger Hunts

Dear Scavenger Hunts,

If this is my husband writing in, please know that you don’t have to create a fake email address and try to sneak your concerns into the Prudie inbox. That’s not healthy communication.

Seriously, my husband could have written this about me—especially me a couple of years ago. Every trip outside the house began with a search for multiple belongings. I was famous for losing Airpods—so much so that I admitted I wasn’t ready for the level of responsibility that owning them requires and eventually decided to just buy multiple super cheap knockoffs so that I could always find at least one pair. I left my laptop in the TSA bin at the airport more than once. It was bad! It’s good that your wife is already medicated for ADHD because that was the first thing that came to mind for me (and what made a big difference in keeping up with my stuff), so I’m sorry it’s not helping as much as she hoped it would.

I’m still not perfect, but here are some additional things that have saved me from a life of constant scavenger hunts for life essentials:

Decide on a home for every object in the house. The key part is that the home (some kind of surface or container) has to be in the place where you’re naturally inclined to drop the thing, or to look for the thing. The basic version of this is having a hook or basket for keys at the front door. She needs a place to place her rings, in the area where she normally decided to take her rings off. And one spot for any papers that may be important. Forget a filing system. If she’s not an organized person, she’s not going to use it. The point is just to be able to throw stuff somewhere where it will be contained and can be found. This will help for sentimental items, too. They’re probably lost because they don’t have a designated place.

Then create another home in each room for random items that need to go somewhere else. So if you’re looking for a kid’s toy that has migrated from the playroom, you’ll know to check the baskets or boxes in the other rooms. And if you see that she’s abandoned her gloves on the bathroom counter, that’s where you throw them.

Stock up on multiples of things that tend to get moved around. For example, just put a phone charger anywhere that anyone might need to charge a phone, so there’s no temptation to unplug one from one place and put it somewhere else.

Identify common hiding places for lost items. For example, I know that for some reason whenever I open my closet, I tend to put down whatever I’m holding on top of the dresser that’s inside it (and then walk away), so that’s one of the first places I look when something is missing. I also know that the one time I let go of my phone is when I’m doing laundry, so it’s often going to be found on top of the dryer. The crack between the front seat of the car and the center console is also a common offender.

Finally, I have a phone case that is also a wallet and has a wrist strap and a place to hook keys. This has been huge for me because, thanks to my phone addiction, I’m rarely going to go without my phone for more than a few minutes, and that means I keep track of everything else too. I replaced a debit card because it expired rather than because it was lost for the first time in my life using this system.

All of these interventions will help and will be essential for keeping track of your future kids’ things, too. And most of it can be achieved without your wife doing much except being open to trying them. (I’m guessing that deciding on and creating new systems might not be a strong suit for her.) But you may also need to practice some acceptance. She is unlikely to transform into a person who always knows where everything is. I know that’s hard to hear, you say you “can’t take it anymore” and I hope that’s not the case because I really believe that with a few tweaks, this problem can be downgraded from unbearable to simply annoying.

To aid in that acceptance, you may want to see what it feels like to take a step back and let your wife handle it if something is lost rather than jumping in to try to help and getting all worked up. If she says she’s misplaced her favorite sweater, you can just say “Oh no. I’ll keep an eye out” rather than turning the house upside down. If there are truly important items that will cause real problems for you if they’re lost (her ID while you’re traveling, the car keys, any essential paperwork, etc.) gently suggest that you be the one to hold onto them. For other things, remind yourself that it’s not an actual emergency when they go missing. Finally, build in some “looking for stuff” time when you are deciding how long the two of you will need to leave the house, because when you’re rushing is exactly when things are likely to disappear. Ask me how I know.

Classic Prudie

I’ve been good friends with a co-worker for many years. I’m a married woman, he’s a single guy, and over the years it feels like our lives have become so intertwined that I never get a break. We go to the same gym, he travels with my family and friends, and he has generally become a part of my social circle. He’s had some difficulty with boundaries and has slept with several of my married friends when they were going through rough patches in their marriages. I’m not worried this will happen to me, but I find that behavior really troubling. He justifies it by saying their husbands weren’t treating them well enough.

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