Feeling Steamrolled in Pennsylvania: how to respond when friends change your plans last minute

05/14/25 • 8 min

7 Listeners

In this episode of Jenny Says So, Jenny dives into the complexities of friendships—specifically how to navigate awkward moments and misunderstandings with grace and empathy. She emphasizes the importance of curiosity and open communication, suggesting that friends should approach conflicts with a mindset of understanding rather than judgment. Jenny shares her tips for creating safe spaces for vulnerability, addressing misunderstandings directly, and handling tense moments with compassion and clarity.

Hey Jenny, I have a dilemma I need help with. So, two old friends and I have been getting together a few times a year for dinner. Since we are a little geographically dispersed, we all take turns being slightly inconvenienced, and we really try to pick a place that is convenient for everyone (as much as possible). For our recent outing, we picked a date, time and place that made sense for us all. However, at the last minute one friend wanted to change the time and place, and the demeanor was a little aggressive! Before you knew it, we had changed our plans to accommodate her. What would be the right thing to say to her to bring attention to the fact that she was inconsiderate? Is it wrong to read aggressiveness in a text? Thanks for the help. Signed, Feeling Steamrolled in Pennsylvania

Jenny dives into this relatable friendship dilemma with her signature compassion and straightforward advice. She discusses how easy it is to misread tone through text and emphasizes the importance of face-to-face communication to clear up misunderstandings.

Jenny shares practical tips on how to address inconsiderate behavior with kindness and honesty, suggesting that open-ended questions can help uncover intentions without placing blame. Her advice highlights the importance of curiosity, understanding, and direct communication in navigating friendships.

Previous Episode

Need Boundaries Advice in New York City: how to manage social obligations when out-of-town people visit you

7 Recommendations

In this episode of Jenny Says So, Jenny dives into the complexities of social obligations when friends or acquaintances visit a city. She emphasizes the importance of setting boundaries, being authentic in interactions, and managing expectations. Jenny also shares practical advice on how to prepare for visitors, including creating a recommendations list and practicing responses to maintain personal well-being.

Hi Jenny, I have a question for you. I recently moved to Manhattan and am about to turn 40, which has me reflecting on how my friendships and social dynamics have evolved over time. I’m an extrovert and an entrepreneur, so I’ve built many connections over the years through work, school, and networking. But now that I’m in New York City, I’m finding that people from my past—some of whom I haven’t seen in years—reach out when they’re visiting the city. They often expect me to act as their tour guide, coordinate their plans, or be on-call for catch-ups, even if it’s not convenient for me.While I value these connections, it feels one-sided and draining, especially when there’s no reciprocity or deeper relationship involved. On top of that, I’ve had situations where people bring others along, making the dynamic even more complex, leaving me feeling like entertainment rather than a friend.As a people pleaser, I struggle with setting boundaries in these situations. How can I create clear criteria for myself to decide when to say yes or no? And are there ways to navigate these interactions so they don’t leave me feeling so depleted? I’d love your thoughts on how to protect my energy while maintaining authentic relationships. Signed, Need Boundaries Advice in New York City

Jenny dives deep into this relatable situation, offering heartfelt advice on setting boundaries, honoring your own time, and not feeling obligated to play tour guide when it’s not genuinely aligned with your energy. She shares tips for gracefully saying no, offering curated recommendations instead of your time, and recognizing when a visit is more about convenience than connection.

Jenny encourages listeners to listen to their instincts, practice direct communication, and prioritize their own well-being without guilt. Her practical advice is perfect for anyone feeling the weight of social obligations and looking for a way to protect their time while still maintaining meaningful connections.