There is something universal about picking up an advice column, because no matter how different our lives may be, we all find ourselves tangled in the same kinds of human relationship questions. We want to be good people, but we also want to protect ourselves. We want to do the right thing, but we often don’t know what that is until someone else helps us see it clearly. The two letters featured here show two very different struggles, but they both deal with the same core issue: how do we manage the emotional weight of our relationships with honesty and kindness? The first letter comes from a father who is watching his teenage daughter manipulate a boy who adores her, and he is disgusted. The second comes from a woman who has spent more than four decades in a friendship that has soured, and she is now wondering whether she should attend her old friend’s funeral someday. Both writers are torn between love and disappointment, between obligation and self-respect. Dear Abby answers them with a mix of firmness and warmth, gently pushing them toward honesty, compassion, and action rather than avoidance. In doing so, she reminds us that the hardest conversations are often the ones that matter most, and that the time to repair or correct a relationship is now, not later.
The first letter introduces a father who describes his sixteen-year-old daughter, Lindsey, as popular, beautiful, charming, and usually well-meaning. She runs with the “in” crowd at school, but she is also friendly and engaging with everyone, which her parents have always encouraged. The problem is Henry, a quiet boy who is not part of her social circle but who is genuinely sweet on her. Henry gets excellent grades, treats people with respect, and is considerate in every way. The father has grown to genuinely like Henry, and he can see that Lindsey has been giving Henry the impression that she is romantically interested in him, even though she isn’t. She has let Henry help her with school projects, she invites him over to keep up the charade, and she has essentially turned him into a personal helper and emotional support without ever intending to be his girlfriend. The father tried to talk to Lindsey about this, but she dismissed the concern with a cold and troubling rationalization: she said she was “just using what God gave her” to better her life, and she claimed that since Henry seems happy being around her, she isn’t doing anything wrong. The father is disgusted by his daughter’s behavior and is considering talking to Henry directly, or at least to Henry’s parents. He loves his daughter, but he doesn’t want to see her destroy the heart of a good kid who has been nothing but kind. Dear Abby’s response is immediate and firm. She points out that Henry may be happy now, but both the father and Lindsey know that he will be crushed when the truth eventually comes out. She tells the father that this manipulation must end immediately, and that Lindsey should be informed she will face consequences if she doesn’t come clean and sincerely apologize to Henry. Abby adds that the father needs to be prepared to follow through with whatever normal discipline he would use with a self-centered, misbehaving child.
There is something deeply painful about watching someone you love act in a way that contradicts the values you tried to teach them. The father in this letter is not just worried about Henry; he is worried about what Lindsey’s behavior says about her character. When a teenager learns that she can use charm and attractiveness to get favors, she is learning a dangerous lesson about power, relationships, and self-worth. She is also learning to see other people as tools rather than as human beings. Lindsey’s comment about “using what God gave her” is especially troubling because it twists the idea of natural gifts into a justification for exploitation. Henry is not a resource; he is a person with feelings, and he has trusted her enough to help her and to believe that her interest in him was real. The father’s instinct to talk to Henry or his parents is understandable, but Abby wisely redirects him to the more meaningful task: making his own daughter accountable. If the father goes behind Lindsey’s back to Henry, he may protect Henry from some immediate hurt, but he will also teach Lindsey that she can avoid responsibility for her actions. Better for her to face the uncomfortable truth head-on, to apologize genuinely, and to understand that behavior has consequences. This is not just about discipline; it is about character. The father has an opportunity to help Lindsey become the kind of person who does not use others casually, who understands that her charm does not give her a license to manipulate, and who knows that real friendship and love are built on honesty. It will be hard, and Lindsey may resist, but the most loving thing a parent can do is refuse to let a child become someone who treats people as disposable.
The second letter shifts from the concerns of a parent to the regrets of an old friend. A woman writes to say that she has had a college friend for more than forty-five years, but over the decades they have had issues. She admits that she has a bit of a temper, and because of that, her friend has said many times that she belongs in a mental institution. The last disagreement happened several months ago, and all communication has stopped. During that final argument, the friend spoke to her in the same tone of voice you would use with a two-year-old, which was humiliating and hurtful. Now the woman is dealing with medical issues that the friend and her husband do not know about. They are no longer young, and the woman is faced with a painful question: if her friend or her friend’s husband passes away, should she go to the funeral? She now uses a walker, and if the church’s chair lift is broken, she would not be able to attend anyway. She also lives quite a distance away, so traveling would be complicated. She signs off as “Estranged Friend in New Hampshire,” and her question is heavy with unspoken emotion. Dear Abby’s response is surprisingly gentle and direct. She notices that the writer never said her friend is the one with health issues, and she gently reminds her that, in light of their long friendship, the friend should be made aware that she is unwell. Abby suggests that the woman tell her friend she would not want their long friendship to end as things stand. Then, addressing the funeral question, Abby reminds her that funerals are intended as a support for the living. If she would like to attend when the inevitable does occur, she should contact the person conducting the service and ask if the funeral home or house of worship is accessible under the Americans with Disabilities Act. There is no need to stay home because of what might go wrong.
This second letter is full of the quiet pain that comes with long relationships that have soured. Forty-five years is a lifetime, and so much shared history is wrapped up in that friendship. There were probably countless good times, inside jokes, late-night conversations, and shared memories. But there was also a recurring pattern of cruelty, with the friend using the woman’s temper against her and suggesting she belongs in a mental institution, which is not just an insult but a stigmatizing and dehumanizing thing to say. Then there was the final word spoken in a tone that reduced the woman to something small and helpless, like a child being scolded. It is no wonder she stopped speaking to her friend. But now she is facing her own mortality, and the question of the funeral becomes a question about what their friendship actually meant. Is it worth attending the funeral of someone who hurt you? Is it better to let the silence stand, or is there too much history to let it end this way? Abby’s advice is wise because it reframes the question. She does not force the woman to forgive or to forget; she simply suggests that the woman reach out because she is unwell. That is not an admission that the friend was right. It is an act of grace, a way of saying that the friendship mattered, even if it was broken. Abby also reminds her that funerals are for the living. Going to a funeral is not necessarily about the dead person; it is about honoring loss, supporting the mourners, and finding closure for yourself. The practical details about accessibility are important too, because the woman’s fear of the broken chair lift is really a fear of being trapped, helpless, and out of place. By telling her to contact the funeral home and ask about accessibility, Abby gives her a concrete way to prepare, so that if she decides to go, she can do so with dignity and without anxiety.
In both letters, Abby’s advice points toward the same reassuring truth: we have more power than we think to repair the emotional harm in our relationships, but only if we act with courage and honesty. The father cannot control what Lindsey does every second, but he can refuse to let her manipulation go unchallenged. He can teach her that using people is not a strategy for success; it is a failure of empathy. The estranged friend cannot undo the years of harsh words and wounded pride, but she can take one small step toward reconciliation by sharing her own vulnerability. She can reach out to her old friend and say that she does not want their long friendship to end as it stands. That kind of reaching out is beautiful precisely because it is not naive; it acknowledges that the relationship has been difficult, but it still leaves the door open for a new kind of ending. Abby does not promise that either situation will be resolved perfectly. Lindsey might still be defensive, and the old friend might not respond with warmth. But the point is not to guarantee a happy outcome. The point is to act from a place of integrity, to speak the truth with kindness, and to stop living in the shadow of what might happen. Dear Abby, written by Abigail Van Buren and carried on for nearly four decades by Jeanne Phillips, has always known that behind every question is a human being who just wants a little guidance. These letters remind us that no matter how old we are, we are still learning how to love, how to apologize, and how to let go. The father may one day watch Lindsey become a more considerate adult because he chose to hold her accountable today. The estranged friend may one day sit in a funeral home and feel grateful that she reached out while there was still time. Life is short, relationships are fragile, and the heart is easily bruised, but we can always choose compassion over convenience.
