Ask Alison: How To Handle 6 Awkward Situations With Grace (And Zero Panic)

From being teased for dressing up to dodging gossip to handling a personal question about your love life, awkward situations pop up more often than we’d like. That’s where etiquette comes in; not as a set of rigid rules but as a gentle guide to help you navigate with kindness, confidence, and just the right amount of charm. In this article, I’ll answer six common “everyday awkwardness” questions, complete with practical scripts you can keep in your back pocket for the next time life puts you on the spot.

Q: What’s the best way to respond when someone says you’re overdressed?

A: We’ve all been there: you walk into the room feeling confident, only to hear, “Wow, someone’s fancy!” Cue the awkward pause. Uncomfortable as it may feel, you don’t need to apologize for looking put-together. A graceful line like, “Oh, I love any excuse to dress up,” says you’re comfortable in your own skin and takes the sting out of their comment. You keep the tone light and you keep your dignity intact. If you are fabulously stylish and find yourself getting asked this question often. Here are a few more lines to keep in mind: 

• “Today is important to me, and I wanted to dress for the occasion.”

• “Dressing up is my version of self-care.”

• “Thank you for noticing! I do love a good excuse to wear this.”

• “I’d rather be slightly overdressed than underprepared.”

Q: I often don’t know if I should hug, shake hands, or wave when I see someone out of the blue. Is there a general rule to follow?

A: This is more of an art than a science, but knowing a little etiquette can help! 

It often comes down to the relationship, how much time has passed since you last connected, and whether it’s a more formal or casual setting. 

The goal is to strike a balance between warmth and appropriateness. A handshake is safe for an acquaintance or former colleague you didn’t know well, but if you’re close friends or family, a hug is often more natural. Context matters too: running into a colleague at the grocery store is different from greeting them at a formal reception. For some reason, people are more inclined to go for more intimate greetings (like hugs and air kisses) the more formal the occasion. 

For example, if you run into a former neighbor at a wedding who you haven’t spoken with in years, because weddings are celebratory and intimate, a hug feels natural and signals you’re happy to reconnect. Now imagine bumping into a senior executive you know from work at a networking event. It may have been months since you last spoke, but a confident handshake accompanied by, “It’s so nice to see you again,” communicates respect while keeping the tone professional.

Q: Do I have to tip for takeout or counter service?

This one trips people up because the iPad screen swivels your way and suddenly you’re staring at 20%, 25%, or 30% before you’ve even gotten your coffee. In general, the higher percentages are meant for sit-down meals where a server is taking care of you throughout. For takeout or counter service, you’re not expected to tip at that same level. That said, leaving a dollar or two, or rounding up, is a thoughtful way to show appreciation. It acknowledges the effort without overextending yourself.

If you pick up a salad bowl at lunch, dropping in a few dollars is kind. At your neighborhood coffee shop, leaving your change or adding a small tip can brighten someone’s shift, too. That said, you can save the 20%+ tips for times when you’re seated and being looked after.

Q: How do I handle it if I get caught in gossip but don’t want to join in?

It’s one of those moments—you’re standing in a small group, and suddenly the conversation shifts into gossip. You don’t want to pile on, but you also don’t want to look standoffish. The graceful move is to keep your response neutral and pivot the conversation. A polite smile and something like, “I haven’t heard that. How’s her new project going?” acknowledges the comment without fueling it. Or you can redirect entirely: “Speaking of work, have you all tried the new coffee shop down the street?”

Think of it this way: you don’t have to police the group or deliver a lecture to avoid being part of gossip. You just have to avoid adding fuel, and then gently steer the conversation somewhere kinder. People usually follow your lead more than you’d expect.

Q: What should I have said when someone gave me an unwanted gift, like a piece of artwork I didn’t want to display in my home?

Gift etiquette is about gratitude, not inventory. Even if the gift isn’t to your taste, the kind response focuses on the thought behind it rather than its future use in your home. A warm, “Thank you so much for thinking of me. What a thoughtful surprise!” honors the giver’s effort without committing yourself to hanging the piece in your living room.

If the gift is from someone close (say, a family member who notices it’s not displayed later), you can be honest without being unkind: “I loved that you thought of me. The colors just didn’t quite fit my space, but your generosity means so much to me.” That way, you balance sincerity with sensitivity.

The bottom line: etiquette doesn’t require you to showcase every gift you receive; it asks you to make the giver feel appreciated.

Q: What do I say if someone asks why I’m still single?

Few questions feel more loaded than this one. It can catch you off guard at a family gathering or even at a wedding, and the subtext often feels judgmental. The key is to respond with confidence and kindness without feeling the need to justify your life. A lighthearted line like, “I haven’t met someone wonderful enough yet,” keeps the tone playful while setting a boundary. Or, if you’d prefer to pivot, “I’m enjoying this season of life. What about you? How have you been?” shifts the focus back to them.

For more formal settings like a work event, brevity works best: “I’m content, and that feels like a good place to be,” paired with a smile closes the topic without inviting follow-ups. Remember, you don’t owe anyone an explanation. Etiquette’s role here isn’t about answering the question fully; it’s about protecting your dignity while keeping the moment gracious.

Depending on your personality and the tone you’re aiming for, here are a few other responses to consider: 

• “I’m really happy with where I am right now.” 

• “I’m focusing on other parts of my life that feel exciting.” 

• “That’s something I like to keep private, but thank you for asking.” 

• “I’m enjoying the freedom to do what I love.” 

• “I’m not in a rush. Life unfolds in its own time.” 

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.”