Ask Alison: Real-Life Etiquette For Every Awkward Situation
We’ve all been there—you’re invited somewhere, asked something, or put in a situation that leaves you wondering, “What’s the gracious thing to do here?”
This week, I’m answering reader questions on everything from word choice to wedding dress codes, from handling nosy comments to navigating romance at work. The through line? Etiquette isn’t about memorizing rules; it’s about connection, clarity, and kindness, no matter the circumstance.
Q: I’m trying to improve my vocabulary and use precise language, but sometimes I worry it comes across as snobby. How do I strike the right balance or know when I’ve crossed a line?
A: A robust vocabulary is a wonderful thing, and a true mark of intelligence. The more words you know, the more precisely and beautifully you can express yourself. For children especially, being exposed to a diverse vocabulary is powerful; it shapes their thinking, sparks curiosity, and expands their world.
That said, the goal in conversation should always be to be understood, not just to sound smart. If your word choice creates a barrier between you and your listener, the connection gets lost, and connection is the heart of communication.
The sweet spot? Choose words that fit both your meaning and your audience. If you’re talking to a group who will appreciate a more elevated term, go for it. If not, find a word that’s clear without feeling watered down. The best communicators adapt to the room without ever dumbing themselves down. They simply meet people where they are.
Q: If someone asks me point-blank if I’m not drinking because I’m pregnant, and I might be, but I’m not ready to tell anyone, what should I say? I don’t want to lie, but am also not ready to share.
A: Just because someone asked you an insensitive and intrusive question doesn’t mean you should accelerate or change the plans for how you share very meaningful news. Big announcements deserve to be shared in your own way, on your own timeline not because someone cornered you at a cocktail party.
You don’t owe anyone your personal information. A warm but firm deflection works beautifully:
“If I had a big announcement, this isn’t the way I’d want to share it.”
“I’m just not drinking tonight.”
“I’ll take a sparkling water, thanks. No need to read into it.”
The key is to keep your tone light so you don’t invite further questions. Smile, pivot the conversation, and remember: you’re allowed to protect your privacy while still being gracious.
Q: Is it ever okay to have a romance at the office?
A: There’s no denying the spark can be real at work, but so can the risks.
The reality is, if things don’t end in “happily ever after,” you’ll still be seeing each other at the coffee machine, and that can get awkward fast. Still, most companies (especially larger ones) recognize that banning workplace relationships entirely is pretty unrealistic.
The real key is how you handle it. Any romance at work should be grounded in consideration, honesty, and respect for your partner, your colleagues, and the workplace itself. And of course, never break company policy; if your employer requires disclosure or prohibits certain pairings (such as between a manager and a direct report), follow those rules.
If you do decide to move forward, keep it professional and mature:
Separate work from romance. Keep personal interactions outside of work hours.
Skip the PDA. Affection belongs off the clock, not in meetings or shared spaces.
Be transparent if required. If your company has disclosure rules, follow them promptly.
Don’t let it affect your work. Meet deadlines, maintain professionalism, and avoid favoritism.
Plan for “what if.” If the relationship ends, commit to staying civil and courteous.
Handled with care, workplace romances can work, but they require more self-awareness, more maturity, and more respect than most relationships outside the office.
Q: A couple I know recently divorced. I don’t talk to them often, but I’d like to get the new mailing address for one of them. How should I ask?
A: While some may find it difficult to receive your message because it can feel symbolic of the finality or the publicity of a separation, many will likely be touched that you care enough to ask.
The kindest approach is to keep it warm, personal, and clear about your intentions. If you have a reason for needing their address, mention it. This way, it feels less like you’re fishing for information and more like you’re extending genuine connection.
For example:
“You’ve been on my mind lately. I’d love to send you an invitation to [event] and want to make sure I have your current mailing address.”
“I’m putting together my Christmas card list and realized I’m not sure I have your most up-to-date address. I’d love to keep in touch.”
If you don’t have a specific reason, you can still be warm and direct:
“You’ve been on my heart lately, and I’d love to keep in touch. Can you let me know if your mailing address is still [your old one] or if it’s changed? Here’s mine as well, just so you have it.”
By pairing kindness with a clear purpose, and offering your own contact information, you make it easy for them to respond without feeling pressured.
Q: I’ve been invited to a black-tie wedding, but it’s being held outdoors in a barn and pavilion. What should I wear?
A: Black tie is black tie whether it’s in a ballroom or a barn. That means floor-length gowns are preferred, though a very fancy tea-length dress can also work. Look for formal fabrics such as silk, satin, chiffon, velvet, or lace, and pair your dress with heels or dressy flats, evening jewelry, and an elegant clutch.
The only difference here is the setting. Because the wedding is outdoors, dress for the elements:
Choose shoes you can walk and dance in without sinking into the grass or gravel (block heels, wedges, or chic flats work beautifully).
Bring a wrap, shawl, or dressy coat in case the temperature dips.
Be mindful of wind and choose your hair style and skirt accordingly, too.
The goal is the same as any black-tie affair: polished, formal, and elegant, just with the practical tweaks that let you enjoy the night without worrying about your footing.
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.”