Dear Abby often receives letters from people who are tangled in painful emotions and unsure how to move forward. The first letter in this collection comes from a man in his forties who is struggling with the aftermath of a workplace romance that ended badly. He and the woman met on the job, though they worked in different departments, and after their relationship fell apart, the atmosphere at work became incredibly awkward. Everyone in the office knew about their history, and he could feel their curiosity and judgment every time he walked past their desks. There were smiles and whispers when he approached, and when he reached co-workers, he was met with silence and intense stares. The burden of being so publicly connected to someone he still cared about was heavy, and he admitted that his feelings for her had not disappeared. In fact, he believed her feelings were still there too, because she had told him so and had shown it through her behavior. But after she ended the relationship, he was hurt and responded by giving her the silent treatment, pretending she did not exist. He knew that this cold behavior had wounded her, and he called himself stubborn, but the truth was simple: he missed her terribly. She had suggested they could be friends, but he did not think he could handle that kind of closeness without longing for more. Instead, he admitted that his desire to fix things and his fantasy of getting back together was probably misguided. He felt stuck, caught between hope and pride, and he asked Abby for insight.
Abby’s response to the first letter was direct and compassionate, cutting through the man’s confusion to reveal a deeper truth: he was the one making the situation awkward, not his co-workers. By choosing the silent treatment, he had put everyone around him in an uncomfortable position, and he had made no real attempt to repair the relationship he claimed he wanted to fix. He said he wanted to reconcile, but he had not even spoken to the woman in any meaningful way. Abby wondered what grounds he had for believing a reunion was impossible if he had never actually tried to talk to her. She gently challenged his self-description as stubborn, suggesting that fear was the more accurate word. He was afraid of being hurt again, and that fear had kept him frozen in a pattern of avoidance and resentment. Abby gave him two clear paths forward: he could muster the courage to talk to his former partner directly, telling her honestly that he wanted another chance, or he could choose to accept the end of the romance and speak to her as a professional colleague, burying the hatchet so they could at least be cordial at work. If neither option seemed possible, and if the pain and tension became too much, then looking for another job was a legitimate alternative. The advice was not about blaming him, but about giving him permission to take responsibility for his own life and his own healing.
This first situation holds a universal emotional truth that many people can recognize. Breakups are hard enough under ordinary circumstances, but when the relationship exists in a shared workplace, the pain becomes public and inescapable. Every glance, every conversation, and every silence can feel loaded with meaning. The man’s desire to hold onto something he lost is natural; so is his fear of making himself vulnerable again. The silent treatment, while childish on the surface, was actually a shield. It protected him from the painful possibility of being rejected once more. What he may not have realized was that the shield was also a prison. In refusing to acknowledge her, he was also refusing to acknowledge his own feelings and his own need for closure. Healing can only begin when we allow ourselves to be honest, not just with the other person but with ourselves. It may be that the relationship cannot be saved, and if that is true, then the kindest thing he could do for both of them was to greet her with warmth and dignity, leaving the door open for friendship or, at the very least, for mutual respect. It is also worth remembering that being “stubborn” is often praised as strength, but when stubbornness is driven by fear, it is simply another form of suffering. Abby’s advice offered him a way out of that suffering, if he would only take it.
The second letter in the column introduces a different but equally painful family dynamic. A person writing from Vancouver, feeling held hostage, described a troubling situation involving their father’s girlfriend, “Jane.” Jane had begun soliciting money for her charitable causes from everyone she knew, especially family members. The writer had donated a modest amount the first time she asked, not realizing it would open the door to a steady stream of requests. The writer had a limited budget for charitable giving and wanted to decide for themselves where that money went. However, declining future requests was risky because Jane and the writer’s father were very sensitive about Jane’s acceptance into the family. They both tended to look for slights and then blow them out of proportion. The father had even made it clear that unless his children fully embraced Jane, he would not be part of their lives. The writer admired her father for standing up for his partner, but also felt trapped, knowing that refusing to donate would likely trigger ugliness. The emotional pressure to give money in order to keep peace in the family felt like a form of coercion, and the writer wanted to know how to escape the situation without destroying their relationship with their father.
Abby’s response to the second letter was grounded in clear communication and compassion. She advised the writer to speak to their father privately, not to Jane, and to begin by telling him that they loved him. From there, they could calmly explain that their charity budget was limited, that they had their own causes they cared about, and that they had already donated to Jane’s projects more than once. It was important to frame the refusal not as a rejection of Jane, but as an expression of fiscal responsibility. Abby also urged the writer to be honest about the deeper emotional stakes: their father needed to understand that these repeated solicitations were jeopardizing the relationship he treasured with his children. The message was not about attacking Jane or demanding that the father choose sides. Instead, it was about protecting the relationship by setting a gentle but firm boundary. Abby’s advice recognized that money can sometimes become tangled with love and acceptance, especially in blended families where people are still learning to trust one another. Jane’s need to be accepted may have been driving her to overreach, and the father’s defensiveness may have been his way of trying to protect her. But neither of those needs justified putting the writer in a position where they had to make a choice between their own financial values and their father’s presence in their lives.
Humanizing this second scenario reveals the complexity of family loyalty and belonging. The writer wanted to be a supportive family member, but they also wanted to be respected as an individual with their own priorities. Jane, meanwhile, was likely searching for a place in the family, and her fundraising requests may have been an awkward way of building connection. She may have believed that participating in her causes would help the family bond, not realizing that the constant asking felt more like an invasion than an invitation. The father’s ultimatum, harsh as it sounded, likely came from a place of fear as well; he may have worried that his children would never accept his new partner, and he felt compelled to defend her at all costs. When we humanize all three people in this story, we see that nobody was acting out of pure malice. They were all responding to insecurity in ways that pushed the family further apart. The writer’s fears about setting a boundary are understandable, because boundaries often feel like walls, but they are actually doors. A healthy boundary lets people see where the limits are, and in doing so, it can create a sense of safety that makes intimacy possible. If the father could hear his child’s words without interpreting them as an attack, he might realize that his daughter or son was trying to stay connected, not push away. And if Jane could understand that a declined donation was not a rejection of her heart, she might relax enough to build a relationship based on something deeper than financial support.
Taken together, these two letters demonstrate how often we hurt ourselves by trying to avoid pain. The man in the first story avoided his ex-lover and ended up suffering more than he needed to. The writer in the second story considered giving in to endless demands just to avoid conflict. In both cases, the path to relief was not avoidance, but honest communication. Abby’s advice, written in a straightforward and no-nonsense tone, is ultimately an invitation to courage. She asks us to look inward and admit what we really feel, to speak our truth even when it is hard, and to take responsibility for our own happiness. She also reminds us that we cannot control other people’s reactions, but we can control how we choose to respond. We can choose to love someone while also saying no. We can choose to let go of a romantic fantasy and instead forgive. We can choose to believe that a parent and partner are not perfect birds, but that they deserve to be treated with honesty. In a world that often feels complicated and painful, these simple choices are not small. They are the heart of growing up. They are how we become mature enough to hold both joy and sorrow at the same time. And in doing so, we honor not only ourselves, but the relationships that matter most to us.
