Dear Prudence

Just a Little Crush

Prudie advises a parent whose son sent thousands of texts and emails to a girl at school.

Daniel 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

Daniel Mallory Ortberg: Hi, everyone! I’m currently in New Zealand, where it’s coming on 6 a.m., so please bear with me. Also: Everyone come to New Zealand, as I have been informed there are no problems here.

Q. My son has been accused of stalking: Last summer, my 14-year-old son Andy went to the same summer camp as his classmate Jenny. He claims they “dated” while at camp and that she “ghosted” him as soon as they came home. I wrote it off as a popular girl dumping a sweet but socially awkward boy due to peer pressure. Recently, Jenny’s parents contacted me claiming that Andy has been stalking Jenny. Unbeknownst to me, Andy sent Jenny thousands of texts and emails; he also called her a lot. Jenny never responded or told him to stop. At school she ignored him. Jenny claims she and Andy never had a relationship. Her parents have wanted to meet with the principal of their school (and possibly with the police) so that we can discuss how to protect Jenny from Andy’s “stalking.” I’m a single mom, and Jenny’s parents are wealthy. How should I advocate for my son?

A: I think you should speak to him with this new information and see how capable he is of responding to it. If he continues with his “summer romance” story, which seems fairly obviously untrue, it may be that he is experiencing a break with reality and needs immediate psychiatric help. You say Jenny never “told him to stop,” and it concerns me that you’re trying to place equal responsibility at her feet. Whether they dated or not, your son (and you!) should be aware that sending “thousands of texts and emails” to someone who has stopped responding is a wildly inappropriate, threatening response to being dumped. He absolutely is stalking her. Whether Andy perceives his messages as friendly or not doesn’t matter; the fact that he has sent thousands of messages to her that are clearly unwanted meets just about every definition of stalking there is. Either way, the best way you can advocate for your son is to find a counselor you can trust and get him the help he needs—and make sure he leaves his classmate alone, for good this time.

Q. Out of the “friend zone”?: I am a 33-year-old woman, and two years ago, while having a fling that ultimately didn’t work out with someone else, I reconnected with a friend from college. He had become really handsome and I grew very attracted to him while my broken heart was healing. He has a girlfriend (no children), but when he talks about her it’s mostly in a mildly complaining manner. I would love for him to think of me as an alternative, but I’m not sure if it’s possible to take myself out of the “friend zone” that I once enthusiastically placed myself in. We see each other about once a month, and while he always seems overjoyed to be with me, he does not do anything to increase the number of encounters. Then again, he is a self-described shy guy who has always needed women to take the romantic initiative. Do I stand a chance, or is it a lost cause? If I should try to take the initiative he needs, how do I do that without coming across as a vulgar and/or deluded home-wrecker?

A: Nothing in your letter suggests to me that your friend is interested in you. It’s possible that he’s too shy to say anything, but that doesn’t mean he’s incapable of doing it—I don’t recommend assuming all shy people are secretly desperate to be wooed by their friends. He sees you once a month, seems happy to see you but doesn’t go out of his way to contact you on a daily basis, and sometimes complains about his girlfriend: It sounds to me like what you have is … a friend.

Q. Seriously putting my foot in my mouth: Three months ago, “Sandra” started working at the same company as me. I’m not going to come off well in this story, and it’s too late to hope for Sandra to like me. Basically, I have asked her three times if she is pregnant/when the baby is due. I’m forgetful by nature and often ask family, friends, and co-workers the same question—although never a question this offensive. Sandra is overweight and sometimes wears dresses that I mistakenly think are trying to emphasize the bump. Sandra has been gracious but increasingly less happy answering me, and I feel like an ass each time. I apologize profusely but by now she thinks I’m making fun of her. How do I convince her otherwise/prevent this from becoming a HR nightmare for me?

A: You say you’re “forgetful,” but if you’re so forgetful that you’re incapable of remembering that a co-worker isn’t pregnant on three separate occasions in as many months, I worry about your memory and cognition skills. The most important thing for you to do right now is leave Sandra alone. Unless it’s work-related, don’t ask her any questions at all. Write it down if you have to—“Don’t ask women if they’re pregnant.” Write it on your hand in Sharpie every morning if that’s what it takes. I promise, if a woman is pregnant and you need to know about it, she will tell you. Your thinking her dress “emphasizes a bump” does not qualify you as needing to know. You’ve already apologized, so don’t go overboard trying to pressure Sandra into thinking you’re a good person. Just leave her alone.

Q. Re: Stalker son: If you’ve ever read Gavin Debecker’s The Gift of Fear, one of the things he suggests to stalking victims is that they avoid engaging with their harassers because any amount of attention can reinforce the behavior they’re trying to stop. Jenny’s ignoring him for as long as possible was a smart choice on her part.

A: Absolutely; it sounds like Jenny is doing everything right in a very unsettling situation. It’s a little worrying that the LW takes this as evidence that Jenny hasn’t done “enough” to discourage stalking. I’m getting a few other letters confirming that the LW’s son is in need of immediate professional evaluation. This is not normal “lonelyhearts” behavior.

Q. How do you even know where we live?: The last person my spouse dated before me had some tendencies one might colloquially call “psychotic”—mainly in the form of lying to manipulate situations. In the 15 years we have been together, this former flame only contacted my spouse one time—to say they had begun a career in my spouse’s field and hoped they might collaborate at some point. I forgot about that entirely until last week. We live in a neighborhood where the houses are very similar looking. A neighbor on our street just put their house on the market. Out of the blue, this ex-partner sent my spouse a message referencing that listing asking if WE were moving. We have no mutual friends with this person and know of no reason other than having specifically staked us out that said person would know where we live and, moreover, what our house looks like. My spouse did not respond to the message. Is this really as creepy as it feels or am I overreacting here?

A: This really is creepy, and I hope the LW from earlier whose teenage son is exhibiting similar behavior can take note. Stalking does not always involve direct threats, but it can often look like a series of outwardly benign check-ins: “Remember, I can always find you. Remember, you cannot choose to end our contact. Only I can do that.” Your spouse was right not to respond, and I hope that their ex continues to keep his messages to an absolute minimum.

Q. Not a black widow: I am 39 years old and have been married five times (widowed four times and divorced once). I married straight out of high school, only to be widowed before the year was out due to the Gulf War. I then married and lost my second and third husbands to a falling tree branch and a drunk driver, respectively.

I had a short, disastrous marriage and divorce after fleeing my hometown, and then I met the love of my life. We had a son and a 10-year union, and he died of a heart attack two years ago. I am just now getting back into dating but on the few dates during which I revealed my history I was met with awkward silence and horrible jokes about my being a “black widow.” It has awakened old nightmares—my former mother-in-law accused me of murdering her son with my bad luck when he died in a car crash! Her drunken daughter was the one driving but it was my husband who died! My entire small hometown decided to scapegoat me for daring to fall in love and trying to start a family! How do I respond to these bad reactions beyond just freezing up? I do not want to be alone for the rest of my life.

A: I’m so sorry for your losses, and I’m keenly aware of how additionally painful it must be to hear some of the most traumatic experiences of your life laughed off as bad luck. There’s something about increased tragedy that decreases sensitivity—I can’t imagine people would tease you if you had only lost one husband, but there’s something about the idea of losing several that renders people incapable of empathy. At the very least, consider this a weeding-out process. You who have suffered so much do not want to be with the kind of person who makes “black widow” jokes to deal with an uncomfortable, painful moment. You should be with a person capable of great compassion and understanding.

I don’t think you need to be alone for the rest of your life, but it may be that you’re not ready even after two years, or at least not ready to date in your old hometown if this is bringing back nightmares for you. If you can’t afford to move at the moment, I highly encourage you to seek grief counseling—you have an enormous amount of tragedy to deal with. There is no need to rush.

Q. My brother-in-law is God’s telemarketer.: My husband’s brother has done well in life—he has a great job, comfortable life, and a beautiful family. He recently decided to give up his job and home to go on a mission to serve as year-round staff at a wilderness Christian camp, family in tow. To do this, he must fundraise about $40,000 a year and recently approached my husband for funds. Neither of us wants to donate as we feel like this mission is motivated as much by his desire get back to the outdoorsman lifestyle he loves as it is by piety, and we are not convinced of the mission’s worth. I would rather donate to a charitable cause in line with my personal beliefs (I’m not Christian). Finally, things are tight—we have good jobs but live in an area with a high cost of living and feel pinched. Is there a polite way to reject future fundraising for this endeavor?

A: What a great setup for him: “I’d like to live in the woods, please send money.” I genuinely hope he gets it! Tell him you’re happy for him but money is tight, and moreover you prefer to give, when you can, to nonreligious charities. Hopefully he’ll understand that just because he’s found his dream job, it’s not the responsibility of his friends and relatives to pay his salary. At the very least, he lives in the wilderness, so he probably can’t call very often.

Q. Re: Black widow?: The Gulf War ended in 1991, which would have made the LW about 15 when it was over. Who graduates and gets married at 15? Seems unlikely. The 2003 war in Iraq was referred to as OIF or the Iraq War so I assume she means “the Gulf War.” Also, she would have been long out of high school when OIF kicked off.

A: The declaring of “fake” I must leave to you, the readers, otherwise I’d be too paralyzed by fear to ever answer a single question.

Q. Brother problem: My boyfriend and I moved in together and, since we’re not getting married, we decided to have a very small get-together (family only) to celebrate. Here’s the thing: I don’t want to invite my brother! He was diagnosed with depression and a personality disorder last year, and has since developed bulimia and a drug addiction. He has been admitted to a psychiatric institution for a few weeks, but since he got out he lies about everything: taking his medication, going to college, seeing his therapist, taking drugs … you name it. I know he will have bulimic episodes if he comes to the gathering, and it will be tricky not to invite him because he lives with my parents. What should I do?

A: I think you should invite your brother. You don’t have to. And if you don’t, you’ll have a number of good reasons. But it sounds like he’s experiencing more pain than he’s causing, and that he’s telling lies not out of malice or a desire to cause chaos but out of fear. If you feared for your safety, I’d advise you not to, but I don’t think he’s a threat to anyone but himself right now. What if you were to invite him while also freeing yourself from the responsibility to monitor his bulimic episodes? Even if he’s struggling with drug addiction and depression, he’s still a member of your family and (presumably) someone you care about. I know addicts sometimes have a penchant for becoming the center of attention at other people’s celebrations, so don’t feel like you have to manage his experience every moment. But have your brother over, and let him know you still support him.

Q. Long-term/long-distance girlfriend unfaithful: This past weekend my girlfriend of 2½ years made out with a random guy at the bar while she was drunk. She confessed, and that’s how I know. She doesn’t have many friends where she lives so she has been out with the few current friends in order to make more friends, but they all seem to be guys. I love her very much but she knows I have had a girlfriend cheat on me before. I am torn and am debating whether to give her another chance. We are at the point in our relationship where I am accelerating grad school to possibly change careers/cities to be with her. It would be at least another year before I would be able to make the move to her city. I saw a future with her before this happened but now I am not sure. Does she deserve a second chance or should I move on?

A: Are you dating last week’s letter writer? If so, she sounded awfully contrite and very serious about her feelings for you, and I think you should try to make it work. It was one kiss and she told you right away—it might be painful, but it’s a one-off mistake, not a habitual pattern of infidelity.

If this is the other half of the same couple, I hope one of you writes back a year or two from now, and lets us know how things work out. Good luck!

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