Dear Prudence

My Husband’s Female Colleague Volunteered to Manage His Email

I don’t want her to see our personal information, and I don’t love that he won’t handle this task himself.

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Dear Prudence,

My husband started his own business decades ago and has always used the same email address for both work and personal correspondence. He has trouble keeping on top of his inbox and often has hundreds of unread messages. I just learned that a female colleague volunteered to clean up his inbox occasionally, going through his unread emails and categorizing them. I’m uncomfortable with this, since plenty of those emails contain information about our doctors’ appointments, our kids, and other family stuff I don’t want his colleagues to know about. I also don’t love that a woman has volunteered to manage a task her male co-worker can’t or won’t handle himself.

He does have a personal account now, but whenever I use it, the messages go unanswered. Now I feel guilty for messing up his system. He says this woman is trustworthy and I don’t need to worry. Is he right?

—Who’s Answering This?

It was an ill-thought-out, badly managed system, and I don’t think you’re the one who messed it up, given that your husband was already having trouble staying on top of it before you voiced an objection. So release yourself from whatever guilt you’re still hanging onto, because things were broken way before you got involved. His defense—that his colleague is trustworthy, so you shouldn’t worry—is nonsensical. Your objection wasn’t “I worry that your colleague will use this information for nefarious purposes,” but “I’m worried that your female co-worker has to pick up your slack and do extra unpaid work because you can’t do something as basic as maintain a separate email account for work and another one for our kids’ doctor’s appointments.”

You say she’s his colleague and not his employee, but if he started the business himself, he’s probably pretty high up on the chain. She may very well have felt pressure to cover for him, especially if his unresponsiveness made her look bad in front of clients, no matter how often she might say that it’s no trouble. It’s exploitative and unprofessional—the problem isn’t that she might be untrustworthy, but that he is. It wouldn’t be unusual for a company founder to hire an administrative assistant to help manage his calendar, sort through his inbox, or remind him about personal appointments, and there’d be no problem if you knew someone was being paid for this work and expected them to share his correspondence. Push some of this guilt off of yourself and onto your husband. It’s long past time for him to either hire someone to do this work for money or come up with a better system for keeping his personal and professional lives separate.

Help! I Love Giving Gifts—a Lot. My Therapist Thinks It’s Weird.

Danny M. Lavery is joined by Aminatou Sow and Ann Friedman on this week’s episode of the Dear Prudence podcast.

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Dear Prudence,

My boyfriend and I have been together for two years, and I couldn’t be happier with him. He’s my favorite person in the world, and I feel so appreciated and supported by him. I even like his family—except for his dad. I’m uneasy and stressed-out around him. Once he invited himself on a long drive with me (that I’d been planning on taking solo) and we sat in almost total silence for seven hours. He turned off the music right away, drank from my water bottle without asking, and made what appeared to be a charged comment about my parents’ ethnicity (I was later assured that it wasn’t).

I’m involved in the Black Lives Matter movement and dread his jokes about how “stupid” it is to try to take down statues of Confederate generals. I end up biting my tongue a lot. My boyfriend’s family keeps inviting me over, and while I’d love to see them (I haven’t seen anyone in a long time due to the pandemic), I’m dreading seeing his dad again. As I look ahead at a possible future with the person I adore, I wonder if I’ll have to spend years feeling awkward around his beloved parent. How should I express this to my boyfriend, if at all? Do I speak up or bite my tongue to keep the peace, especially as a guest in their home?

—Dad Silence

Consider what your life with your boyfriend might look like if you committed to never mentioning your discomfort with his father even once: hiding your dread in the lead-up to every family trip, biting your tongue every time another relative informs you that you’ve “misunderstood” one of his racist comments, covering moments of awkwardness or distress with a tight smile, all the while worrying that your boyfriend has already intuited that something’s wrong but doesn’t want to know what or why. Even if things really are great the rest of the time, that’s an awful lot of time dedicated to keeping your feelings from your boyfriend. Why is protecting him from possible hurt so much more important than protecting yourself from your own discomfort?

You say your boyfriend appreciates and supports you. Is he in the room when his father makes dismissive jokes about racism and the Confederacy? Does he later assure you that you’ve misunderstood those jokes, too? Or does he pretend not to hear them? What does he think about your involvement with Black Lives Matter, and does he share your commitment? Perhaps most importantly: Are you really afraid of breaking your boyfriend’s heart, or are you afraid that if you tell him, he’ll say that you’re making a big fuss over nothing? You’re not asking your boyfriend to cut ties with his father or denounce him in the public square. You want to tell him what’s been bothering you, enlist his support in declining impromptu “Can I come too?” requests in the future, and ask him to push back when his father dismisses your civil rights work. Those are very modest requests to make of someone you want to spend the rest of your life with. Give yourself permission to make them.

Dear Prudence,

My girlfriend and I have been together for three years (we’re both women). “Kay” has a habit I find gross, and we’re at an impasse over it: She is constantly selling her stuff. Clothes, jewelry, shoes, small pieces of furniture … almost anything. She’ll do about two big sales per year. She then immediately spends all the money she made on new stuff. Kay always loses money in the sale—the items are in fine shape, but obviously won’t sell for as much as she originally paid—and, more importantly, it comes off as materialistic and selfish. I obviously find this whole cycle weird, but wouldn’t mind as much if she sold these items to a thrift store or donated them to a local charity. I’m worried that people in our small community are starting to view both of us as just out to make a buck off of others. I also don’t like that Kay seems so unwilling to just let items go without profiting. We come from similar backgrounds, so I don’t think this is a reaction to childhood deprivation. She just seems miserly. We have no other big issues and are happy together. Should I be treating this as a dealbreaker? Is it too much to hold an intervention? Please help.

—Garage-Sale Frenzy

If you want to treat this as a dealbreaker, you certainly can, although I’m not convinced this habit is especially gross. Your girlfriend has a biannual garage sale because she likes to go shopping and doesn’t want a house overflowing with duplicate items. She doesn’t expect to break even from these sales or delude herself into thinking a side table or a new jacket is a sound financial investment. She just wants to defray the cost of a summer wardrobe overhaul. It’s not the most eco-friendly habit in the world, and if she’d written to me, I might encourage her to consider cutting back to an annual sale or making more donations, but I don’t think it makes her irredeemably selfish, either. And I definitely don’t think you need to displace your own discomfort onto your neighbors whom might think of her as a venal opportunist for reselling a lightly worn trench coat. They don’t seem to worry about this half as much as you do! If you really can’t bring yourself to let this go and believe you two simply hold incompatible views about money, shopping, and what the neighbors might think, you can certainly decide to look for another girlfriend. But don’t waste your time or hers by trying to hold an intervention over her rummage sales.

Catch up on this week’s Prudie.

More Advice From How to Do It

I am a woman seeing a new man, and we waited a few dates to sleep together, mostly because he didn’t try. I didn’t think much of it, but when we did have sex, he was sheepish to take off his underwear, and yep, it turns out he has a small penis. This is OK for me—I do prefer some size, but he’s eager and good at other things, so I am not too worried about it. (I’m pretty sure he’s below average, if you’re wondering what I mean by “small”; I’d say 4 inches or fewer.)

He eventually opened up and confirmed the reason he waited to initiate sex is that he wanted to get to know me a little bit so I wouldn’t reject him outright. I was a little hurt by this, but I understand he’s had bad experiences. However, he also told me that his past experiences with women, especially as a teenager, have given him a fetish to be ridiculed for his small penis. I guess it happened enough that it turns him on. Basically, he was embarrassed to tell me he likes to be embarrassed because of his junk. This just feels wrong to me. I don’t want to “kink shame,” or whatever, but I also do not think it’s right for me to further pathologize a normal dick variation, even if he wants me to. I also feel like he should get therapy for this. What do you think?