Ask Alison: Modern Manners For Messy Moments

From navigating awkward Venmo requests to politely dodging milestone questions, modern etiquette isn’t about being perfect, it’s about being thoughtful, gracious, and just a little more polished than the table napkin stuffed in your water glass. Let's get into it.

Q: Is there a right way to order at a restaurant, or am I overthinking it?

A: You’re not overthinking it, you’re just showing a little polish. And in a world of “I’ll do the salmon,” a touch of refinement makes all the difference.

When your server approaches, close your menu to signal you’re ready. Make eye contact, smile, and speak to them, not the page.

Stick with something simple and courteous: “May I please have the duck?” “I’d like the burger, please, ” if you’re having a Taylor Swift Polo Bar moment. (Here’s how to order like she did.) Saying “I’d like” rather than “I’ll have” is a small shift, but much more considerate. Skip pointing at the menu unless there’s a true pronunciation hurdle, and even then, a quick “How do you pronounce this one?” can be more graceful.

And don’t feel pressure to recite the full title of a complicated dish. “The risotto, please,” works beautifully.

It’s not about being formal, it’s about being thoughtful. Good manners put people at ease, even in the most casual settings, and that includes your server.

Q: I’m always the one in our group who organizes the plans, makes the dinner reservations, and actually gets ideas out of the group chat. I don’t mind taking the lead, but being the planner has gotten expensive. People forget to Venmo me, they don’t think about taxes, fees, or tips, and sometimes they cancel last-minute after I’ve already paid a deposit. What’s the etiquette here? How do I keep things fair without sounding petty?

A: First, thank you for being that friend—the one who makes things happen. Every group needs someone who turns “we should do something fun” into actual plans. Your effort, energy, and enthusiasm are a gift. But even thoughtful leadership needs boundaries.

First, let’s talk about communication. So much of this can be avoided with a little clarity up front. When you’re organizing something that requires splitting costs, like a group dinner, concert, or weekend getaway, spell out the key details ahead of time. A simple message like:

“Hey friends! This comes to $52 each with tax and tip. I’ll put down my card to reserve it, but please Venmo me by Friday!” This goes a long way in setting expectations.

You can also be proactive about cancellation policies:

“Heads up—this place charges for no-shows, so let me know by Thursday if anything changes!”

Still, even with clear communication, things can go sideways. If someone forgets to pay you back, send a polite nudge:

“Just a reminder on dinner last weekend, your share was $48. Thanks so much!”

And if a friend cancels last-minute after you’ve already paid a deposit? It’s okay to say, “I completely understand, life happens! Unfortunately, they charged for the full headcount, so let me know if you’d still be able to cover your portion.”

If you’ve been footing the bill and it’s starting to wear on you, financially or emotionally, please don’t let guilt stop you from resetting. You might say something like:

“I love planning, but I’ve realized it gets tricky for me to keep covering group costs upfront. Would everyone be open to paying ahead of time going forward?”

That’s not petty, it’s sustainable. Thoughtfulness should go both ways. Setting a clear standard helps ensure your generosity isn’t mistaken for unlimited bandwidth or indifference.

Q: My mother-in-law has no idea how to set a table. We’re talking napkins stuffed into glasses, knives facing the wrong way, gaudy centerpieces that block conversation, and don’t even get me started on the serving utensil situation. Would it be rude to say something?

A: It can be hard to hold your tongue when you have a strong eye for detail and a special place in your heart for a beautifully set table. I get it! But etiquette isn’t about pointing out what someone’s doing wrong. It’s about respect and creating a sense of comfort. And correcting someone, especially your mother-in-law in her own home, likely won’t put her at ease.

Unless she specifically asks for your input, I’d recommend letting it go.

That said, don’t underestimate the quiet power of leading by example. The next time you’re hosting, take the opportunity to set a beautiful table with intention and care. People notice, even if they don’t say anything, and over time, your approach might gently inspire others to elevate theirs.

And if you’re planning something together, like a holiday meal or bridal shower, that opens the door to a more collaborative conversation. You might say:

“I’d love to take the lead on the tablescape, would you be okay if I handled the setup this time?”

Or, if she’s in your kitchen and eager to help:

“Thank you! I actually have a particular way I like to set the table, but I so appreciate you offering.”

Lead with grace. Keep it light. And remember: even if the forks are flipped and the centerpiece blocks half the guests, the real charm of the table is the people around it.

Q: I’m a new mom, and our sweet boy has some disabilities that aren’t always obvious to others. It’s really hard when, even with the best intentions, people ask questions about his developmental milestones. Sometimes I’m open to sharing, but I’m often not. How can I respond in a way that’s both dignified and clear, sets a boundary, and doesn’t invite a deeper conversation that I’m not ready to have? 

A: First, I want to say that your instinct to lead with dignity and protect your child’s story is not only valid, it’s deeply loving. There’s a difference between being open and being available. You don’t owe anyone access to the most personal parts of your journey, especially in moments that catch you off guard.

Questions like “Is he walking yet?” or “When did she start solids?” might seem harmless to the person asking, but that doesn’t mean you have to answer. If talking about developmental milestones feels triggering or invasive, you’re allowed to respond in a way that gently closes the conversation.

Here are a few phrases that set a boundary without inviting further discussion:

“We’re on our own timeline, and I’m learning to love that.”

“He’s making progress in his own way, and we’re so proud of him.”

“We’re keeping the focus on what’s working for him right now.”

If you want to signal even more directly that the topic is off-limits:

“That’s not something I’m really talking about right now, and I appreciate your understanding.”

“I’ve learned that milestone conversations aren’t always helpful, so we’re skipping those for now.”

You can say these things with warmth and confidence. You don’t have to explain, justify, or take on emotional labor for other people’s curiosity.

And remember: you’re allowed to respond differently on different days. Your boundaries aren’t rigid, they’re wise. Protecting your peace and your child’s privacy is etiquette. And it’s a form of love, too.

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.”