Dear Abby: Navigating Friendship Dilemmas and Life’s Disappointments
In today’s column, we explore two heartfelt letters that touch on the complex nature of friendship, trauma recovery, and the pursuit of life dreams. These stories remind us that even in our most challenging moments, finding a path forward is possible with self-reflection and courage.
The first letter comes from a woman in Wisconsin who belongs to a close-knit group of friends she’s known for decades. These women gather monthly for dinner and drinks, rotating restaurant choices based on whose birthday they’re celebrating. While this tradition has been a source of joy, it’s become complicated for our letter writer. She occasionally skips these gatherings when they choose a restaurant frequented by a man named Bob—someone who traumatized her twenty years ago. Shortly after her first husband’s death, Bob broke into her home, stole items from her late husband’s office, and frightened her by entering her bedroom while she was dressing. Though he claimed he was “checking on her,” the experience left her with lasting psychological scars. Despite Bob’s troubling history, which her friends acknowledge, they continue patronizing his regular hangout because he’s a “jolly bar guy” who buys drinks. Some friends have even suggested she should “get over it,” failing to understand the depth of her trauma. This situation has created a painful dilemma: miss out on cherished time with friends or risk triggering her PTSD.
Abby responds with compassion, validating the writer’s traumatic experience and offering practical advice. She suggests the letter writer continue declining invitations to gatherings at Bob’s hangout and reconsider how “wonderful” friends who knowingly put her in such an uncomfortable position truly are. Abby also recommends professional help from a mental health specialist if her PTSD symptoms persist. This response recognizes a fundamental truth: real friendship includes respecting boundaries and acknowledging trauma, not dismissing it for convenience. The writer deserves friends who prioritize her well-being over maintaining a comfortable relationship with someone who caused her harm, regardless of how much time has passed.
Our second letter comes from a 38-year-old in Indiana who has experienced three broken engagements. Though marriage remains a cherished dream, each attempt has ended in disappointment, leading to uncertainty about whether this dream will ever become reality. The writer asks whether to keep hoping for marriage or to set this aspiration aside. This question reflects a common human dilemma: how long should we pursue a dream that seems increasingly elusive? When does persistence become self-defeating? Many people face similar crossroads when long-held desires—whether for marriage, career success, or other life goals—fail to materialize despite repeated efforts.
In her thoughtful response, Abby encourages the letter writer to engage in meaningful self-reflection about what went wrong in each engagement. This isn’t about assigning blame but about identifying patterns that might be preventing lasting relationships. She then suggests creating a fulfilling life independently of the marriage goal—pursuing interests, adventures, and activities that bring personal satisfaction and growth. This approach serves two purposes: it creates a rewarding life regardless of relationship status and potentially introduces the writer to compatible people through shared interests rather than through actively searching for a partner. Abby doesn’t suggest abandoning the dream of marriage entirely, but rather reframing it as a possibility that might emerge organically while living a rich, self-directed life.
These letters, though different in circumstance, share common themes about respecting personal boundaries and finding fulfillment despite life’s disappointments. The first writer must stand firm in her boundaries even when friends pressure her to compromise her well-being. Her trauma response isn’t something to “get over” but a valid reaction to a frightening violation of her safety and privacy. Similarly, the second writer faces the challenge of honoring their desire for marriage while creating a meaningful life that doesn’t depend on achieving this particular goal. Both situations require courage—the courage to maintain boundaries and the courage to reimagine dreams when reality doesn’t align with our original vision.
Dear Abby’s column has endured for generations because it addresses these universal human struggles with wisdom and compassion. Founded by Pauline Phillips (the original Abby) and now written by her daughter Jeanne Phillips, the column provides a space where readers can seek guidance on everything from family conflicts to ethical dilemmas. In both responses today, we see Abby’s characteristic blend of practical advice and emotional insight, acknowledging the pain of each situation while offering constructive paths forward. Whether dealing with insensitive friends or adjusting life expectations, her message emphasizes self-respect and personal agency in creating a life of meaning and connection.
