Ask Alison: The Graceful Way To Handle Flaky Friends, Oversharing Coworkers, and First Dates

Modern life comes with its fair share of awkward moments—flaky friends, TMI coworkers, and first dates that feel more like background checks. In this Ask Alison column, etiquette expert Alison M. Cheperdak helps you navigate it all with poise, boundaries, and just the right dose of grace.

Q: My friend always cancels on me last-minute. How do I address it without drama?

A: Let’s start with this: you deserve to feel valued in your friendships. Life gets busy, and things come up, but if a friend consistently bails last-minute, it’s not just flaky, it’s hurtful. The kindest way to bring it up is one-on-one and in a low-stakes setting.

Try this: “Hey, I’ve noticed lately it’s been tricky for us to actually get together. I completely understand that things come up, but I wanted to check in, are you feeling overwhelmed? Should we pause on making plans for a bit?”

You’re not accusing, you’re opening a door. And you’re giving her a graceful out and a chance to do better. Friendships thrive on honesty with empathy.

And if you’re experiencing repeated cancellations in your love life, check out this piece for more. 

Q: I’m the only single friend in my group. How do I handle it gracefully when plans always seem to revolve around couples or kids?

A: You’re not imagining it; friendship dynamics do shift as people get married, have children, or enter new life stages. And while love and little ones are worth celebrating, it can leave you feeling like you’re living on a different planet, or at least a different calendar.

First, a gentle reminder: your presence is not lesser just because it’s not attached to someone else. You bring your own joy, energy, curiosity, and charm to any room you walk into, and that’s something your friends should value. That said, etiquette is about creating connection, not waiting for others to make room. So yes, it’s okay, and actually kind, to gently advocate for more inclusive plans.

Try something like: “I’d love to spend time with you, maybe just the two of us sometime soon? I miss our girl time.”

Or:

“I totally get that things revolve around family these days, but if you ever want a night off from the chaos, I’m your girl.”

It’s also okay to quietly excuse yourself from events where you feel more like a prop than a guest. Etiquette isn’t about enduring discomfort, it’s about showing up well and knowing when to preserve your own energy.

And if your friendships no longer feel reciprocal or respectful? That’s your cue to expand your circle, not out of bitterness, but from a place of grounded grace. Seek out friends in a similar season. Cultivate connections that don’t require explaining or apologizing for your stage of life.

You’re not behind. You’re not less-than. You’re simply in your own timing, and there’s deep beauty in that.

For more encouragement, Evie has beautiful reads on embracing your singleness and wisdom for the woman who thought she’d be married by now. You're definitely not alone.

Q: Is it rude to Google someone before a first date?

A: It's not rude, just realistic. A quick search is modern self-preservation, not a breach of etiquette. That said, you’re not writing his memoir. A light check to confirm he is who he says he is? Smart. Digging up his sister’s LinkedIn and the Zillow estimate on his apartment? Overkill.

When you do meet, don’t pretend you don’t know things you do, just don’t lead with them. Let him share his story in his own words, and listen like you’re hearing it for the first time. Curiosity is cute. Creeping isn’t.

And if you’re curious what a good first date even looks like, you’ll want to read this. 

Q: My coworker overshares. How do I set boundaries kindly?

A: We all have that one colleague who treats the office like a therapy session. And while compassion is important, so is your bandwidth. The secret is to stay kind and consistent.

Try something like: “I’m so sorry you’re dealing with that; it sounds heavy. I wish I could talk more, but I’ve got to finish this before lunch.”

Or even:

“I always want to be supportive, but I’ve realized I don’t have the bandwidth for deep conversations during the workday.”

You’re not rejecting them, you’re rerouting the energy. Over time, they’ll get the hint. And if it’s something that starts to feel uncomfortable or inappropriate, loop in your manager or HR. 

Grace doesn't mean being a doormat. It means drawing boundaries without burning bridges.

If you have a question for a future Ask Alison segment, kindly email info@elevateetiquette.com.

Alison M. Cheperdak, J.D., is the founder of Elevate Etiquette, a consultancy where she teaches modern manners in a gracious and grounded way. She is the author of a forthcoming book, “Was It Something I Said? Everyday Etiquette to Avoid Awkward Moments in Relationships, Work, and Life.”