Dear Prudence

Nuts on Dates

Prudie counsels a 32-year-old virgin too anxious to go out with women.

Mallory Ortberg, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up below to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at

Readers! Ask me your questions on the voicemail of the Dear Prudence podcast. Just leave a message at 401-371-DEAR (3327), and you may hear your question answered on a future episode of the show.

Q. 32-year-old virgin: I’m a 32-year-old straight man and I’ve never been in a relationship with a woman. I can count on one hand the number of dates I’ve been on. I’ve had many female friends and am perfectly comfortable around women in that context, but as soon as it’s a “date” my anxiety takes over and ruins everything. Although a professional has never formally diagnosed me, I’m pretty sure I have avoidant personality disorder (I have all the symptoms listed on various psychology websites). I’m afraid of going to therapy or taking medication. I’m sure you would advise me to try either of those things. What bothers me is that even if I went to therapy and was able to manage my anxiety, I worry about reactions to my lack of romantic experience. Do I try to hide it for as long as possible or be totally up front about it? I feel like I’m past the point of no return, and it’s just too weird to date now.

A: It’s a bit difficult for me when a letter writer both predicts what I’m going to say and forestalls me by saying they’re not going to do what it is they think I’m going to say to them. But I’ll give you my best shot. If your goal is to become more comfortable socializing with women, I’d advise you to spend more time with friends in a less-intimidating setting than first dates. If your goal is to find a romantic relationship, I’d advise you to be very upfront with women before you go out about your social anxiety, as naming certain fears and dynamics often (but not always) removes some of the power from them. Consider dating women who also experience social anxiety, or who at least have some familiarity with conditions like yours and who are not put off by it. I’d also encourage you to pursue therapy, despite your fears. You mention being afraid to see a therapist in-person but seem comfortable searching for your symptoms online; there are numerous online-only treatments for anxiety that you may find helpful. I can’t vouch for any of them individually, but certainly some treatment is better than none. I also want to give a plug for seeing if marijuana alleviates any of your symptoms, if you’re comfortable trying it and don’t fear using it compulsively. That doesn’t mean you should get majorly high for the first time right before a date, but it’s worth considering what small doses might do for your anxiety. It’s not a magical cure-all, and it might not be right for you, but it merits a mention, all the same.

I don’t want to rush to reassure you; I have no idea if you’ll ever have a romantic relationship. But I do think that it would be worth finding avenues to manage your anxiety even if it never results in your having sex or finding a girlfriend. Improved stability, calm, and a sense of mental well-being would be good goals in and of themselves, even if your romantic life never improved as a result.

Q. Overstay: I own a two-bedroom, one-bath condo that is right in the heart of downtown and close to work, family, and friends. My long-term boyfriend has lived with me for three years and everything was awesome until his brother’s house accidentally burned down. Everyone is OK and the insurance will cover the cost of rebuilding, but now my boyfriend wants his brother, sister in-law, and their large dogs to come stay with us for the next six months. His parents live three hours away in the country so a commute is impossible on a daily basis. The dogs are large, poorly trained, and completely destroyed the backyard at the old house, and the sister in-law is a slob. She is a sweet girl, but I am constantly picking up wet towels from the floor, putting up dirty glasses, and closing cabinets she leaves open when they visit for a weekend. I will go crazy if I have to live like that full time. My boyfriend is putting pressure on me saying I let my family stay with us (for a week at Christmas) and a friend for two months while she house-hunted (we barely saw her). I’ve been focusing on the dogs and suggested they stay in his parents’ backyard and I get called heartless. I am fine with the brother staying with us during the week and that get shot down. I feel guilty, ashamed, and mad all the time. I don’t want to wreck my relationship over this! Help!

A: If your boyfriend’s brother’s insurance is willing to pay for the rebuilding, they will also pay to put them up while they are effectively homeless; “additional living expenses” are part of homeowner’s insurance. Now would be the time for any insurance agents in the audience to let me know if I’m way off the mark. Is there ever an instance where a company would agree to pay to rebuild a customer’s home, but not to cover the cost of living expenses while their actual home remained unlivable? Regardless: six months of two houseguests and their poorly trained dogs? That merits a “hell no.” They’re not suddenly out of work, their insurance is paying to repair the house, and they are not without options. What they’re asking for goes way above and beyond the call of family duty, and suggesting that you are “heartless” by asking them to consider putting their dogs with family in the country for six months is rude, manipulative, and overdramatic. Stand your ground.

Q. Recovering memories: My mother and I are no longer speaking, on my own terms. During my childhood, she neglected me and allowed her boyfriends to abuse me verbally. I can’t move on from the pain while she’s in my life, so I cut contact. My issue is that I’m attempting to move on from my father’s abuse and subsequent death 15 years ago as well. My mother has all the pictures, videos, etc. of what little childhood I spent with my father, and it would really help the grieving process if I had access to those memories. Do I attempt to ask her for them? Do I have the right to ask in the first place? Should I try to move on without those memories?

A: What a painful position you’re in. I’m so sorry that the only tangible mementos of your childhood are in your mother’s hands. It may have been an unpleasant childhood, but it’s the only one you’ve ever had, and I understand your desire to revisit it, albeit in a carefully controlled way. While I do think you have the right to ask, I don’t encourage you to do so, because I cannot imagine your mother, who has previously been neglectful and abusive, would simply hand over the photos just because you asked her to. I think she would deny you, or try to start a fight, or offer them in exchange for some demands she’s had in waiting, or some terrible combination of all of the above. It may be that seeing your old childhood photos would help you grieve, but I don’t think they’re absolutely necessary to building a satisfying adult life away from your family. Seek that out in therapy, with healthy friendships and relationships, in solitude, in nature, but don’t reopen contact with a mother you don’t trust over this.

Q. My new co-worker is too nice!: I act as a sort of Gal Friday in my office. I have a lovely new co-worker in a position higher than mine for whom I often do small tasks as part of my job description. During the first few weeks of her being here, she would buy me coffee when she went to the coffee shop near our workplace as a token of thanks for my help in getting her settled in. However, she’s now been here for a couple of months, and she’s still getting me coffees—between one and three times a week! I am flattered by the thoughtfulness and appreciation, and I always thank her profusely, often offer to pay her back, and ask if I can get her anything when I make runs for food or drinks. But I worry that she feels locked into this habit now and might not want to get me coffee anymore, but feels beholden to because that’s what she’s established. I don’t want her to think I expect this from her! Is there a way I can politely let her off the hook—to say, “Thanks so much for the coffee, and they’re so appreciated when you bring them, but you really don’t need to feel like you have to do this all the time”?

A: If she’s both senior to you and you’ve repeatedly offered to repay her or return the favor, I don’t think you have to worry that she’s accidentally trapped herself in a pattern of debilitating helpfulness. (Her presumably higher salary likely defrays the $5 to $10 a week she’s spending on you, and she may even have a discretionary budget for situations like this.) If it’s really troubling you, you can always politely decline when she asks if you want anything from the coffee shop.

Q. Dating someone with trauma: I have a friend of a few years that I’ve shared a mutual attraction with. However, circumstances never worked out that we were both single and living in the same place at the same time, so we’ve never pursued a relationship. Things changed recently, though, so I had been planning on finally asking him out. Before I could do so, my friend was caught up in an extremely violent episode. He came through it with relatively minor injuries, but it has left him with a fair amount of emotional trauma. It’s been almost two months, and he’s over most of the physical issues, and has been in counseling, but I know he still struggles with the mental fallout of the whole episode. I’m torn; I want to go ahead and ask him out now, but I want to be sure that I’m being sensitive to his emotional needs. On one hand, I tell myself that if we did start dating, I could help support his recovery, but on the other hand I don’t want to jeopardize his healing process, particularly if things didn’t work out between us. Maybe he’s not ready, and if he did start dating, it would just be an emotional crutch, rather than the support he needs? And then I ask myself if it’s still too soon, when would be the proper time to initiate anything? How would I ever know what would be the appropriate cutoff between too soon and enough time has passed? I just keep going through all of these questions, and don’t know what to do.

A: This is someone you’ve known and trusted for a long time, and who knows and trusts you. I think you should feel comfortable asking him if he feels ready to consider dating, because you’d like to ask him out. There’s no timeline for recovery here; it’s entirely up to him. He’s physically healed and doing his best to address his emotional trauma. He might feel overjoyed at the prospect of some good news, or he might feel unsure and unready. You’re not doing anything wrong by asking. I think, based on your letter, that this is your primary concern—that there’s some invisible timeline you’re ignoring and if you ask him “too soon” you could somehow cause a psychological relapse. But that’s not how trauma works, and you should feel comfortable asking him what he wants. Tell him, “I trust you to be honest with me about what you are and aren’t ready for. I think you’re cute and I’d love to go out with you. If you don’t feel up to dating just yet—or if you’re no longer interested in going out with me—let me know, and I won’t mention it again, because our friendship and your recovery are important to me. If you do, I’d love to take you to dinner sometime.” (And write back with updates! May fortune attend your quest!)

Q. Wondering why a friend won’t speak to me: I had a good friend growing up who has shut me out of her life and I have no idea why. We were close as kids, and then she and her family moved to another state. We stayed in touch sporadically, but our connection seemed genuine. Then a number of years ago she stopped responding to me. I have written to her via email and actual letters, and left messages on her voicemail, but never get a response. I send Christmas cards every year to her parents, and they often respond with letters about what they’re up to and also about her life, but I never hear from her. After my mother passed away, I couldn’t find her parents’ contact info, so I emailed my friend via a social media site to let her know and asked her to tell her family. She did so, but didn’t respond to me, not even to send a single word of condolence about my mother, whom she was close to growing up. I’m OK with having lost this friendship, but I remain completely baffled about what I did to make her cut me out of her life. There was no conflict between us, no tension, just a sudden silence that’s now gone on for years. In a situation like this, do you think it’s worth contacting the person and asking why? If I did something that hurt her, I’d like to know. I considered mentioning to her parents, the next time we correspond, that “Beth” won’t speak to me, but that feels a bit passive aggressive. From the tone of their letters, they don’t know. Should I leave them out of it, let this go, and just accept that this will remain a mystery?

A: Leave them out of it. We don’t know if Beth simply found it easier not to maintain your friendship due to distance and laziness, if she harbors a secret resentment against you for something you said or did that mortally offended her, if she feels so guilty about losing touch with you that it’s easier to pretend you don’t exist than to acknowledge all the times she’s failed to respond to your friendly overtures, if she was secretly in love with you and keeps you at arm’s length out of self-preservation—yeah, it’s a mystery. Asking her parents to mediate your estrangement is unwise. She’s an adult and you should not try to pressure her family members into forcing her to divulge something she’s decided to keep to herself. As frustrating and unpleasant as it may be, she does have the right not to speak with you. You’ve asked repeatedly, and she’s refused to reply, and while you don’t have to like it, you do have to respect it.

Q. Not a cafeteria: I am a Southern gal who has always prided myself on my cooking and hosting ability. I have a secret addiction to Pinterest. I have happily hosted luncheons, bridal showers, baby showers, and paid-my-college-loan parties, but since I have moved to the West Coast with my husband, I have been at a loss. I understand religious or dietary restrictions, but I have never had someone who wasn’t over the age of 3 tell me they don’t eat mushrooms. Or crunchy food. Or fish. It is a bizarre fixation, where trying to plan a dinner party is like planning a war campaign. Never in my life would I think to tell a host to their face that I was unhappy because the food wasn’t exactly to my taste. Or having a lemon meringue pie was horrible faux pas because I forgot Brittany hated lemon. This keeps coming up every time I start trying to assemble a steady group of friends. Am I missing something? A generational thing (my husband and I are in our early 30s)? A West Coast thing? It has gotten to where I only want to bring out the wine and go out to eat, but I miss entertaining in our lovely new home.

A: Potlucks, and stop inviting Brittany over. Brittany is rude as hell. Just say “no thanks” when you’re offered a slice of lemon meringue, Brittany.

Mallory Ortberg: Until next week, I tear myself from your respective sides.

Discuss this column with Dear Prudence on her Facebook page!

If you missed Part 1 of this week’s chat, click here to read it.