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My boyfriend loves me, but he won’t tell me he loves me.

Mallory Ortberg
Mallory Ortberg
Sam Breach

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Dear Prudence,
I’m in a six-month relationship with an amazing guy. He’s kind, generous, funny, and supportive, and we click on all levels. He treats me better than any man who ever said he loved me—but he’s not ready to say it yet. I’ve said it already, and I don’t regret saying it because I know I mean it. He says he feels the same thing I do but isn’t ready to call it love—he wants to wait until we’re further down the line toward commitment before saying it. His only other relationship lasted for six years and ended badly, so he’s very cautious this time around. He also wants to wait until he knows where his job will be and where he’ll be living.

I know this is something you can’t force, but it’s really bothering me. I have absolutely no complaints about how he treats me. That’s why I want to tell him I love him practically all the time! But I have to hold back because I know not hearing it back will hurt. I also don’t understand why outside factors like where he’ll be living would influence how he feels about me in the first place. How do I process this and not fixate on it but allow myself to be happy with someone who clearly cares deeply about me, even if he can’t say the same words I do? And is there a time limit by which he should say it? I’m just so worried he’ll never say it at all.
—Three Little Words

This is such an individual thing that I’m almost reluctant to give you any advice more specific than “Do what you think is right for you.” Your boyfriend has made it clear that he’s not ready to say he loves you and he’s given you a number of reasons for that decision. Whether or not you think those reasons make sense, whether or not his decision can work for you, whether or not there’s a point at which you would need to hear “I love you” in return in order to continue your relationship, those are questions that only you can answer. There’s no one-size-fits-all time limit, no date by which all boyfriends have to say, “I love you,” or become loveless monsters.

I can say a few things with relative authority. I think your best way forward is to share your fears with your boyfriend. I think that “having no complaints” about how he treats you is not necessarily a reason to stay in a relationship if you decide it’s not working for you. I think that his previous romantic relationship may provide useful context for where he’s coming from but is ultimately irrelevant to how the two of you relate to one another. If you think it’s odd that he’s willing to say he all-but-loves you unless and until he gets a job lined up, then I don’t think you should try to convince yourself to stop “fixating” on it. I think you should pay attention to your own feelings, which matter every bit as much as his. That doesn’t mean you have to offer him an ultimatum tomorrow, but don’t spend too much time trying to convince yourself that it’s silly to care about hearing “I love you” in response. It matters to you. That’s important, and you should be honest about it, and see whether the two of you can work through this together. If you can’t, it doesn’t mean you threw away a good relationship for frivolous reasons.

Dear Prudence,
I own a rental house down the street from my own residence. I rent it a bit below market with the understanding that tenants will be “easy.” The current tenants (a couple and their 8-year old) have been generally OK, if not the best I’ve ever had. However, I’ve recently heard from a few neighbors that “Tommy” is a terror at school and has bullied several neighborhood kids. They’ve hinted that I might do our local elementary school a favor if I didn’t renew their lease. (I am within my rights to do so; it ends in May, and I would give 60 days’ notice.) There are very few rentals in the local elementary school catchment area, so “Tommy” would likely end up at a different school next year were his family to move. My neighbors are nice people, and I doubt they are exaggerating—and they have always been welcoming to my tenants in the past. Any advice on how to handle this?
—Playground-Tenant Dispute

You have an opportunity here to not get involved in someone else’s parenting challenges, and I suggest you take it. If Tommy is causing problems at school with someone else’s children, then it’s up to the school and Tommy’s parents to address it. As long as Tommy’s parents are living up to their half of the rental agreement, there’s no reason for you to evict them based on secondhand information that their kid is a bully. Even if Tommy is in need of serious discipline, he’s also 8 years old.
Not to mention the fact that simply sending him to another school would do nothing to address his behavior! This is a situation that calls for some classic, old-fashioned butting out.

Dear Prudence,
About two years ago my parents separated and are now divorced. They both had affairs, and my dad left my mother for the woman he had an affair with. We’re still working on blending the families, but two of my siblings, one in particular, have refused to accept my dad’s fiancée. My brother has said that he will not budge until they break up. My dad says that he’s done appeasing my brother and has to stand up for his relationship. I’m worried that he’s about to torpedo his relationship with my brother, but I can hardly expect him to end his engagement. My brother steadfastly refused to go to my dad’s for Christmas and continues to reject any of my dad’s attempts to get them in the same room together. I don’t know how to talk to either of them anymore. How do I help keep my family from falling completely to pieces?
—Family Breakup

I know this isn’t the answer you were hoping to hear, and I know you’ve already had to deal with a lot of destabilizing new developments over the last couple of years, but your first and most important task is to resign from the job of “person responsible for keeping the family together.” Your family is still your family even if your parents get divorced, even if your brother and your father keep fighting, even if your brother and your father stop speaking to one another. I imagine that lately it feels like everything is out of your control and that your family is disintegrating, but as long as you make yourself responsible for keeping everyone together, you’re going to drive yourself crazy—not to mention set yourself up for failure.

Encourage your brother and your father to talk to one another, then let the subject drop. After that: Talk to your brother about any subject that isn’t your father. Talk to your father about any subject that isn’t your brother. Remind yourself, whenever the little anxiety engine in the back of your mind that whispers, “This family is dissolving into pieces and if you don’t do something right now, we’ll never be able to be a family again” starts to fire up again, that you cannot manage your father’s and your brother’s relationship for them, and that you will be OK no matter what happens between them.

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Dear Prudence,
I grew up in far-from-privileged circumstances, but I typically got what I wanted, particularly away from home. Maybe I just had a way with the adults in my life, but I considered myself a hard worker who demonstrated persistence and determination. Yet, now that I’m a sophomore in college, I’ve been forced to reckon with the fact that my peers—who, in this setting, have more influence—aren’t as easily persuaded by my own persistent efforts to achieve a goal. Over the past year and a half, there have been a number of setbacks where I’ve felt powerless to alter the outcome, which I’m not used to. Could you give some advice on how a college student could adjust to this change and leverage it for future success?
—How to Adjust to Not Getting Your Way?

I think it’s probably worth developing a more nuanced attitude to failure for its own sake, not merely because you think it might result in future success. Part of the college experience—part of being a young adult regardless of whether you go to college or not—has to do with experiencing failures and setbacks, sometimes for the first time without familial aid. They’re often surprising, they’re generally unlooked-for, and they usually hurt. That’s not to say that you have to resign yourself to every failure that comes your way, or that there’s no value in persistence and determination—simply that figuring out how to deal with disappointments is an important component of becoming a well-rounded adult. I can’t promise you that learning to lose gracefully will ultimately become part of a strategy for future success. Silicon Valley promulgates a belief in eternally transformative failure, that every single failure brings one closer to a more thoroughly optimized outcome, and I don’t think that’s true. On any given day, in any given circumstance, there will be a number of things that are totally outside your control, and any number of outcomes you will be absolutely powerless to alter. Failure is inevitable, and therefore it’s important to figure out how to respond to each individual failure with relative equanimity—whether that leads to a later success or not. You can be a persistent, determined person, a hard worker, and any number of other positive attributes and still fail; it’s not a reckoning on your individual worth. Consider these current failures as good training for the rest of your life.

Dear Prudence,
I have reconnected on social media with a former girlfriend, and she has become a very close friend. We dated briefly in our early 20s. It was an intense relationship that fell apart because we were both young and immature. I am now a middle-aged, divorced single dad; she is happily married with two daughters and lives several states away. The chemistry between us is unmistakable. She even came back to my area (alone) several months ago to visit family, and she invited me out for dinner and mentioned that her husband was in poor health. The remark about her husband’s health was only in passing. We didn’t have a whole conversation about that. But as you can tell, I put a whole lot of meaning into it. I can tell she has feelings for me. How strong, I don’t know, but she clearly loves her husband and their kids.

I am absolutely smitten with her. I think about her every day. We talk on social media maybe once a week or so. I don’t want to break up her family or even sow any hint of trouble there, so I haven’t told her how I feel. On the other hand, it is hard to think seriously of anyone else romantically—just in case something happens in her husband’s life. And I feel like total shit for even thinking that. If I break off contact with her, I lose a good friend. And how do I do that? And what do I say to our mutual friends? I know I am in a destructive pattern, but I don’t know what to do.
—Can’t Extinguish Old Flame

This is the sort of thinking that can quickly spiral out of control in a closed environment like the inside of your own head. The next time you find yourself obsessing over your ex, I think it might be helpful to counter some of your fantasies with reality.

Fantasy: She mentioned that her husband’s health isn’t great! Maybe he’s going to die soon, and the two of us can get back together, and I’ll be 22 again.

Reality: My ex clearly loves her husband and her kids. I know that she’s happily married. I will never be 22 again. I am middle-aged and divorced and have to deal with the complicated feelings that engenders within me. We had dinner once a few months ago. Now we talk about once a week and there seems to be some sort of charge between us that, while pleasant, does not incline her to express a wish to leave her family to be with me. The fact that I think about her every day has more to do with me than it does with her.

You don’t have to say anything to your mutual friends, because there’s nothing going on, aside from a rekindled friendship that may or may not carry a slightly flirtatious vibe. (I’m inclined to take your claim that you “can tell” she has feelings for you with a grain of salt, not because I don’t think she likes you, but because you’re clearly bringing a lot more intensity to the table than she is.) I get where you’re coming from! This is a woman you have an intense, albeit brief, romantic history with, who’s re-entered your life during a time when you’ve been feeling a little adrift, and you’ve been reminded of all the reasons you connected with her in the first place. But if you’re having trouble putting her out of your mind to such an extent that you’re not able to go on dates or focus on your own life, then I recommend you see a counselor and spend some time figuring out why you’re so fixated on this ex in particular. That’s a healthier and more productive strategy than hoping your ex’s husband dies in the next year or two, then feeling guilty about it.

Dear Prudence,
I recently decided to try a little light bondage with my boyfriend of just over a year. I stripped down, put on a blindfold, and let him tie me to the bed. Then I waited. And waited. Finally, I pushed off the blindfold (it was very light bondage!) and saw that I was all alone. I found him in the living room and asked what was wrong. He said nothing was wrong—he just wanted to see how long I would lie there. I called him a jerk, and we got into an argument. He said it was just a joke and that I should lighten up, but I’m still angry. Am I making too big a deal out of this?
—Unbound in New York

That move goes in the Bad (Ex-)Boyfriend Hall of Fame. The fact that he wants to call it a joke doesn’t mean you don’t get to feel angry and hurt about it, or ask him why he decided to make a joke out of your sex life or why he thought it would be funny to leave you alone, confused, bound, and vulnerable. Calling something “just a joke” is not the get-out-of-jail-free card some people think it is. The fact that he hasn’t apologized and doesn’t seem especially interested in how it made you feel says a lot about what you can expect from him in the future.

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