Dear Abby: Navigating Modern Tipping Expectations and Family Dynamics

In today’s economy, tipping etiquette has become increasingly confusing and sometimes uncomfortable. One reader from Idaho shares their frustration with the seemingly endless expectation of tips in every service interaction. They describe pulling up to a cookie store drive-through, only to be asked about tipping before even receiving their order. Their niece experienced something even more jarring when a server actually followed her outside a restaurant to question why she had left a smaller tip. With rising prices everywhere, the traditional 20% guideline feels increasingly burdensome, especially when simple transactions like drive-through service now come with the implied obligation to tip. The pressure creates awkward moments, with disappointed looks from service workers making customers feel guilty for not contributing extra.

Abby responds with practical wisdom, acknowledging that many service workers depend on tips to supplement their sub-minimum wage earnings. However, she firmly states that tips should never be directly requested, and a server confronting a customer about tip size is completely inappropriate. While some establishments now suggest tips as high as 35%, Abby notes that most customers typically give between 15-20% of the total bill for adequate service. Her straightforward advice to the reader is simple: if you believe you received good service, leave an appropriate tip without complaint, and you’ll likely be welcomed warmly wherever you dine. This pragmatic approach acknowledges both economic realities for service workers while respecting the customer’s right to determine appropriate compensation based on service quality.

Family gatherings should be occasions for connection and joy, but sometimes they become sources of tension and discomfort. Another reader writes about a monthly music trivia night they organized with their brother and sister-in-law, hoping it would strengthen their relationship. Unfortunately, what started as a fun activity has become uncomfortable because the sister-in-law consistently belittles her husband (the reader’s brother) in front of everyone. What the reader and their spouse initially mistook for playful banter has evolved into something more concerning. The brother typically remains silent during these interactions, apparently preferring to avoid confrontation, but this passive approach leaves everyone feeling awkward as the evening concludes. Now the reader faces the difficult decision of whether to continue inviting them to these gatherings.

Abby’s advice on this family dynamic is direct but sensitive: have a private conversation with both the brother and sister-in-law together, explaining that public criticism makes everyone uncomfortable. This honest approach addresses the problem without being accusatory. Abby acknowledges this conversation might result in the couple choosing not to participate in future trivia nights, which would effectively solve the immediate problem. However, if they do continue to join and the behavior persists, Abby suggests simply ending participation without further explanation. This balanced approach respects everyone’s dignity while establishing clear boundaries about acceptable behavior in social settings.

The questions posed to Dear Abby highlight how social expectations and interpersonal dynamics have grown increasingly complex in modern times. Whether navigating the evolving landscape of tipping culture or addressing uncomfortable family situations, many people struggle with setting appropriate boundaries without causing offense. Both scenarios reflect broader societal tensions: service workers depending on inconsistent tipping systems while customers face financial pressures of their own, and families trying to maintain harmony while addressing problematic behavior. These situations require a delicate balance between honesty and tact, between standing up for oneself and maintaining important relationships.

Dear Abby’s enduring appeal comes from her practical, straightforward advice that acknowledges real-world complexities. Founded by Pauline Phillips and now written by her daughter Jeanne Phillips, the column has guided readers through changing social norms for generations. The advice offered doesn’t shy away from difficult truths – sometimes you need to speak up about uncomfortable situations, and other times you simply need to accept social conventions like tipping as part of participating in society. What makes Abby’s counsel particularly valuable is how she balances empathy for all parties involved with practical solutions that preserve dignity and relationships whenever possible. In an increasingly complicated world, this combination of compassion and clarity continues to provide a valuable roadmap for navigating life’s interpersonal challenges.