Dear Prudence is Slate’s advice column. Delia Cai is filling in as Prudie for Jenée Desmond-Harris while she’s on parental leave. Submit questions here.

Dear Prudence,

I need help handling my boyfriend’s attitude about work. In every other area, our relationship is going great, and I think if I find the right words to say this, he will hear me, and we’ll be able to figure this out. I’m a 27-year-old woman and have been with Charlie, who is 29, just shy of a year. He hates his job. He has to deal with not great corporate bureaucracy and has a bad boss who looks to him to manage the team because Charlie has more experience. He is actively applying to new jobs, but has not had many solid leads, I think because of the holidays. Despite the steps he’s taking to leave, Charlie’s attitude about his job is really difficult to interact with.

He acts like it’s the worst job in the world, like he’s the unluckiest guy in the world, and like work is more difficult for him than anyone else. I can get where he’s coming from, working can suck! But his current job offers him such great tangible and intangible benefits. He gets paid well, has remote flexibility, and works only about 30 hours/week. This flexibility allows him time to pursue time-consuming hobbies and take a nap every day. Meanwhile, I work a job in a traditional field that is notorious for overworking its employees. My employer is pretty good, but I work about 45 hours/week exclusively from the office. I am really tired of his complaining. Every meeting on his calendar is a slight against him and everything his boss does is for the sole purpose of making his life miserable. I suggested talk therapy to help him cope during his job search, and he wasn’t offended by the idea but didn’t seem too interested. I guess I am struggling because 1) it’s a lot of complaining to me every day, 2) his job is pretty good to him, and I don’t think he knows how good he has it in some regards, and 3) I worry this is just his attitude about work generally and he will be similarly miserable in any job. He has picked up on my thoughts about his job’s perks and has felt invalidated because of that. I don’t want him to feel that way, but I need help.

—Not Looking for a Provider, Just a Partner

Dear Partner,

There’s a fantastic scene in Sex and the City (Season 2, Episode 13) where Carrie’s friends confront her about her needing to see a therapist because they can’t take her obsessing about her on-and-off again beau Mr. Big anymore. This may sound trite, but I think you should give that scene a watch because it’s a perfect example of how to tell a loved one that their complaints are starting to become above your pay grade—or “It’s out of our league,” as Charlotte says.

When you talk to your boyfriend, make the issue about how it’s obvious that you’re simply not able to offer the support that he needs when it comes to his feelings about his job, and that it’s time to call in the big guns (aka, professional help). Tell him that you know that he’s unhappy and that he needs an outlet to dissect every frustration related to the job hunt and his less-than-ideal work situation, but that it’ll be infinitely better for your relationship if you’re not the go-to repository for those complaints.

It may be that his sense of entitlement and his attitude will ease up once he’s channeling his frustrations through a proper outlet. For many people, turning 29 represents a major moment of personal reckoning, whether or not you actually believe you have to have life “together” by age 30. (To which I’ll say: Only boring people do.) Give your boyfriend the benefit of the doubt as he works through this turning point, but also permit yourself these observations about how unattractive you’re finding his current work ethic. See if you can notice these things without reading too much into what they mean. At this stage in a relationship, you’re naturally going to start figuring out what parts of your partner you actively dislike. That’s part of the journey! What matters right now is that you make your immediate needs known, and that you give the relationship (and your boyfriend) a chance to keep growing.

Dear Prudence,

I think I might be the problem, and I want to hear it straight. My husband works from home, and I sometimes commute an hour-plus away. We have two kids in school. I would say 10 percent of the time when I call him, he’s unreachable for up to an hour (doesn’t respond to calls or texts). The explanations vary—he forgot his ringer was off, he was on a work call, or he fell asleep away from his phone. He’s apologetic but it doesn’t stop

But it makes me INCREDIBLY anxious not to hear from him. Even though he does this frequently, I always end up worried he’s keeled over from a heart attack or injured himself with his power tools. And I always think about what I’d have to do if one of the kids was sick and needed to be picked up immediately and he was incommunicado. Or that he’ll sleep through meeting the kids at the bus stop. When he finally does get in touch, I am inevitably furious.

I’ve told him all this, that his behavior is unacceptable and ratchets my anxiety sky high. He promises he’ll do better, but he never does. I’ve gotten so, so angry at him over this and it makes no difference. Are my expectations unreasonable? I know I’m probably angrier than I should be because my anxiety is higher than it should be. What do I do? I can’t change him, but that’s what I want the solution to be. If I could snap my fingers and not care, that still doesn’t fix the potential problems of kids stranded at the bus stop or a sick kid waiting around at school.

—Whose Fault Is It That I’m Left to Wonder If He’s Dead?

Dear Fault,

From my personal perspective, your husband taking up to one hour to respond roughly 10 percent of the time you call seems fairly reasonable. I do think your expectations to have him effectively on call during the day are rather high, but I don’t think this anxiety of yours materialized out of nowhere. I would advise you to talk to a good therapist about these fears and where they came from. Was there an obvious inciting incident in your past where it was actually debilitating to not be able to get ahold of someone?

If your primary concern is not having a constant stream of reassurance from your husband that he’s present and healthy, perhaps you can negotiate a specific lunchtime check-in or a code for when you just want to hear that he’s OK. But I’m not convinced it’s fair to expect anyone in one’s life to never go more than an hour without checking their phone. When it comes to your concerns about kid-related emergencies, I believe on most phones you can change the contact settings for the school’s phone number so that any call from the school will ring with a different ringtone or volume; there should be a feature called “Emergency Bypass” on your phones. Make it crystal clear to your husband that this phone number (and/or that of your kids) needs to be able to get through at all times. But otherwise, you may need to address your more helicopter-y habits on your own.

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Dear Prudence,

What should I say to a guy who I have no romantic connection with (we went on a date but he said he didn’t feel a romantic connection, and I totally agreed, we are not suited), but keeps messaging me? They have been friendly messages up to now, although he often tries to meet up for a drink or events, which I always refuse. But he’s now sending me topless selfies, photos of him sunbathing, and some sexual jokes. I want to try and tell him it’s not acceptable without being too aggressive. Also, am I being too sensitive in finding this creepy and off-putting?

—Creeped Out

Dear Creeped,

You’re absolutely not being too sensitive. I think you’re well within your rights to simply block him without explanation. If you prefer a different approach, you can be direct and say, “I’m confused why you’re texting me like this if we’re not pursuing a romantic connection.” It sounds like he’s bored and wants attention, and you’re the nearest source. Make it clear that he needs to pick a new one.

Dear Prudence,

I’m finally in a relationship with a man I see a future with. That being said: I find myself regularly thinking about an ex. This ex is not someone I can have a future with based on their maturity level, among other things. However, I felt very understood by them and connected to them. We have a friendly relationship. Meaning I do not spend time with them, or go out of my way to see them but we do run into each other on occasion and it can leave me really overwhelmed and confused after we chat for a bit. I sometimes wonder whether we should be together. Logically, I recognize this is probably just my brain’s way of fantasizing while I am entering my first very calm relationship. I think with time this will probably go away but my brain keeps nagging at me and I keep dreaming about him. What do I do?

—Can’t Get You Out of My Head

Dear Head,

It’s absolutely normal to spend some time comparing your current relationship with one from your past, especially if there was a genuine connection. If I were to use the parlance of attachment theory as an extremely unlicensed civilian, I might say you’ve probably got a bit of an avoidant impulse in you that’s a little freaked out about being in a calm, healthy relationship. Your brain is going overboard analyzing and justifying such a big decision to be this close to someone new (and who’s so different from your ex). If you’re anything like me, you might find true intimacy and compatibility to feel so uncomfortable that you start daydreaming about alternate lives or escape routes.

The advice I’ve gotten is this: You’ll likely always wonder a little bit about “what might have been”—that’s human nature, and maybe just our personalities. But if that daydreaming is getting in the way of your happiness in this current relationship, or you’re toying with the idea of becoming friendlier with this ex, you may need to seek out a good therapist or some dedicated alone time to consider what unresolved questions you might have about this past relationship. But overall, I wouldn’t read too much into it. It’s natural that your brain is having a little compare-and-contrast field day, simply because finding a great connection is so rare.

—Delia

Classic Prudie

I’m a 28-year-old woman who used to have a tight, supportive friend group, but I seem to have alienated them all since dating “Aaron.” I met Aaron in my hometown during a really bad time with my family (involving drug abuse and a young relative’s death). He was supportive and made me laugh when I really, really needed it, and the sex was incredible. Because of this, I overlooked A LOT of problems with him.