Few advice columns have managed to capture the messy, tender, and often contradictory nature of human relationships quite like “Dear Abby.” For decades, the column has served as a quiet confessional, a place where strangers write in with their most private struggles—grief, guilt, resentment, and the awkward gap between what we feel and what we know we should do. In a recent collection of letters, the wisdom on offer is remarkably human: it acknowledges that love is not always neat, that closure is sometimes impossible, and that the best we can do is act with kindness, even when we are uncertain or hurting. The first letter comes from a person still mourning the loss of a long and complicated friendship. The writer, “Cared for Him in the South,” explains that a friend named Ben and he shared thirty years of ups and downs, marked by periodic blowouts and reconciliations. Three years ago, they had one of their usual falling-outs and stopped speaking. The writer later discovered that Ben passed away a year after that, but no one had told him. The online obituary gave no cause of death. A letter of condolence to Ben’s widow was returned, and the widow had since moved away. The writer cares deeply, wants to know what happened to his friend, and is tempted to reach out through Facebook, even though it feels impersonal and heavy. Abby’s advice is simple, practical, and protective: find mutual friends and ask privately. She warns against approaching the widow online, especially because the friendship was strained at the time of Ben’s death. It would be off-putting and possibly hurtful. Underneath this advice is a deeper truth—grief does not require permission, but our methods of seeking it should be gentle, respectful, and mindful of others.
The first letter resonates because so many of us have unresolved relationships with people we once loved. We assume there will be time to fix things, to apologize, to understand, to say goodbye. But life does not always provide that tidy ending. When someone dies before reconciliation, the grief is tangled with guilt and regret, and the unanswered questions can feel unbearable. The writer’s desire to know what happened is not mere curiosity; it is a need to place a final stone on a friendship that mattered, even if it ended in silence. Abby’s response gently redirects that need toward a safer avenue—not social media, not a direct message to a grieving widow, but trusted people who can share information with care. There is something profoundly humane in this advice. It recognizes that the writer deserves closure, but not at the expense of a widow’s emotional safety. It also reminds us that friendship, even a broken one, leaves a permanent mark. The writer can honor Ben privately, perhaps by writing his own letter and keeping it, or by remembering the good years without demanding an explanation for the bad ones. The hard truth is that sometimes we never learn the whole story, and we have to find a way to carry our love and our loss without resolution. That is not failure; it is part of being human.
The second letter shifts from the finality of death to the discomfort of being celebrated. “Older in Israel” is about to turn sixty-three, but has never enjoyed birthday celebrations. He would prefer the day be completely ignored. He knows his wife of nearly thirty-eight years, along with their two sons and their significant others, are planning something. He wishes they would spend the money on themselves or donate to charity instead. His question is a familiar one: should he say something and risk causing ill will, or just grin and bear it? Abby’s answer is refreshingly practical and empathetic. She reminds him that his wife, who has been with him for almost four decades, likely already knows his feelings. The solution is not silence and resentment, but a gentle conversation. He should tell her he knows something is being planned, express his preference for a small celebration, name a charity he cares about, and suggest the birthday budget be sent there rather than spent on him. But then Abby adds a crucial caveat: if his wife ignores his plea and a big party happens anyway, he should endure it with grace and a smile, because the people celebrating him are doing so out of love. This advice is beautiful in its balance. It encourages honesty without demanding control, and it reminds us that our loved ones often express affection in the ways they know how, even when they miss the mark. A birthday is not just about the person being celebrated; it is also about the joy of the people who want to celebrate them. Sometimes accepting love—even awkwardly, even in a form we do not enjoy—is itself a gift.
This second letter touches on a universal struggle: how to honor our own preferences without hurting the people we love. Many of us have felt trapped by a celebration we did not want, or frustrated by a gift that showed more enthusiasm than understanding. The urge to push it all away, to say “spend it on charity,” is often rooted in a deeper discomfort with being the center of attention or receiving generosity. But Abby’s advice gently challenges that impulse. She validates the man’s wishes, but she also asks him to consider the intentions behind the party. The party is not a trap; it is an offering. And there is something humbling about accepting an offering with gratitude, even if it is not exactly what we would have chosen. This is the kind of advice that applies far beyond birthdays. It applies to holidays, family gatherings, weddings, and all the rituals where our individual preferences meet collective love. We can set boundaries and communicate honestly, but we must also know when to soften and let ourselves be cherished, even imperfectly. In a world that often celebrates independence and self-sufficiency, Abby’s gentle reminder to receive love is a quiet act of wisdom.
The third letter addresses a quieter, more private kind of struggle. “Crushing in Illinois” is married and has developed a crush on a co-worker after four years of working together. He is clear that he will not pursue anything because cheating is against his morals, but he still feels guilty for having the feelings at all. He asks what he can do to get his feelings in check. Abby’s response is short but remarkably freeing: guilt is a good thing because it has kept him from making a terrible mistake, and crushes usually lessen over time, even if they make the present uncomfortable. This advice is so compassionate because it separates thoughts from actions. It acknowledges that attraction and infatuation are not always choices; they can arrive unbidden, even in happy marriages. What matters is what we do with them. The writer is already doing the right thing by not pursuing the crush, and his guilt is not a sign of failure but a sign of his moral compass still working. Abby does not shame him for being human. She does not suggest he quit his job or confess to his wife. Instead, she offers the reassurance that this, too, shall pass. In a culture that often equates feelings with identity, Abby’s wisdom is a reminder that we are not defined by every fleeting emotion. We are defined by our commitments, our choices, and our willingness to let uncomfortable feelings exist without letting them rule us.
The final piece in the column is not a letter but a note from Abby herself: a Happy New Year to readers of the Jewish faith during Rosh Hashanah, a time of repentance and reflection, when observant Jews make amends and seek a closer relationship with God. This brief blessing ties the entire column together. Each letter has been about the need for reflection, amends, and the courage to handle complicated feelings with grace. Whether it is reaching out after estrangement, accepting a birthday celebration we never wanted, resisting a temptation that goes against our values, or simply finding peace with an unresolved loss, the underlying message is the same: life is full of difficult human moments, and our job is not to be perfect, but to be kind, honest, and willing to grow. Abby’s advice, across decades and hundreds of letters, has always been grounded in this kind of practical compassion. She does not offer harsh judgments or impossible standards. She offers understanding, boundaries, and hope. The man who lost his friend may never get his answer, but he can honor the friendship in his heart. The man who hates birthdays may still have to smile at a surprise party, but he can do so knowing he is loved. The married man with a crush can hold steady, wait for the feeling to fade, and be proud of his integrity. And all of us, at the start of a new year, can take a moment to reflect on our own relationships—the ones we have hurt, the ones we have neglected, and the ones we still have time to heal. That is the real gift of Dear Abby: not a rulebook, but a reminder that we are all imperfect people doing our best, and that kindness, patience, and honest communication are the threads that hold us together.
