Hi Everyone,
Welcome back to Ask Leslie — the monthly advice column where you get real answers to real-life dilemmas, no identity required. This month’s DMs landed right where love meets boundaries. We’ll be navigating family vacations, dodging political questions, and carefully deciding whether an old friendship deserves a comeback (been there!). The common thread was clear: how do we honor ourselves and our relationships at the same time?
There’s no script for these moments, but the thoughtful choices we make speak the most. As always, my goal isn’t to tell you what to do — it’s to help you trust yourself as you do it, like any good friend would. Let’s dive in!
xx
Leslie
For the past few years, our family has vacationed one week over the summer in Nantucket with my parents in a shared vacation rental. It’s been fine, but it never quite feels like a true vacation with so many people under one roof. Now that our two kids are older, we’d like to rent a vacation house just for our family. How do I tell my parents our plans without hurting their feelings, especially knowing they value this time together and may not be able to afford a similar rental without sharing the cost?
Dear Nantucket Negotiator,
This is a potentially sensitive topic, especially since you’ve had this tradition going over the past few summers, and your parents might just assume you all are vacationing again and budgeting for it.
While this summer shift might come as a surprise to your parents, I think that family traditions are fine (and healthy!) to evolve, just as families do. Your parents may see this Nantucket week as a symbol of closeness, not just a vacation, so let them know that your desire to vacation separately isn’t about distancing yourselves — it’s about embracing your new phase of family life.
Position this as a “this year” decision rather than a permanent thing. That softens the message and leaves room for future flexibility, assuming you’d be open to their company down the road. You’re not closing the door; you’re just opening a new one for yourself and your own family.
You might also explain that now that the kiddos are older, you’re wanting a chance to reconnect, just the four of you.
And if you have siblings, consider looping them in. It’s possible one of them would welcome the opportunity to continue a summer vacation tradition with your parents, which could help everyone feel included.
— Leslie
How can I respond to a political question without oversharing or offending the person asking? Is it reasonable to treat politics as a private matter, and if so, what’s the best way to say that politely?
Politics. Yikes.
It’s completely reasonable to treat politics as a private matter. When asked a political question, try answering the person, not the question. Acknowledge them, then redirect. Phrases like, “I try to keep my political views personal,” or “I’ve learned I’m happiest keeping politics out of my social relationships,” are polite.
Adding something like, “I enjoy hearing different perspectives; I just don’t always share my own,” keeps a neutral tone, and most people will take the cue and move on.
It’s smart to keep politics off-limits with people outside your inner circle. I’ve seen differing political views ruin relationships. Protecting your relationships sometimes means protecting your privacy — and that’s totally OK!
— Leslie
Around five years ago, I cut off a 20-year friendship. My former friend has recently reached out wanting to reconnect, but I’ve hesitated to respond. I ended the friendship after ongoing concerns about her personal decisions and how they conflicted with my values. There were other issues as well, but that was the tipping point. While I feel healthier with distance, I do miss the friendship at times. How can I tell whether reconnecting is wise, or whether some doors are best left closed? She also lives over 200 miles away.
Dear Letting Go (or Not),
Ending a 20-year friendship is a big deal, and the fact that you still think about it means it mattered. You’ve already named something important though: you feel healthier. As you decide what to do, ask yourself what value it would add to your life now.
Don’t feel like reopening the door is needed for closure either. You’re doing fine. You can treasure the good memories without re-inviting the relationship, and you can choose to respond slowly or not at all. Either choice takes courage and effort. The healthiest decision may simply be honoring why you closed the door.
I’ve experienced a very similar situation myself. I chose to close the door and keep it closed, and with time, I’ve come to see that I’m better off for it.
I’ll be thinking of you —I know this is tough.
— Leslie
Got a question you’d love an outside perspective on? You can submit it by sending me a DM on Instagram at @ask_leslie_official. As always, all questions are published anonymously — and chances are, if you’re wondering about it, someone else is too. Thanks for following along!