Awkward Conversations: What to Say So They Don’t Get Worse

Awkward conversations get worse when everyone pretends nothing happened. The fix is simple: say the obvious thing lightly, choose what happens next out loud, and move on to a normal topic. Most awkward conversations last ten seconds — unless you drag them out.

How to handle awkward conversations in 4 steps

Say the obvious thing, lightly
Choose what happens next out loud
If it’s fixable, say it quickly
Move on to a normal topic

Leaving a coffee shop, you ran into Wen, who works on another floor of your office. You chatted for a few minutes, said 'Well, see you around!', and both turned to go. Then you both started walking in the same direction, toward the same building, side by side.

Wen

Oh, ha. We're... going the same way.

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How to handle awkward conversations in 4 steps

Awkward conversations are mostly the ten seconds after something weird happens. Handle those well and awkward conversations shrink back into normal ones.

1 of 4

Say the obvious thing, lightly

In awkward conversations, everyone has already noticed the weird part. Naming it with a small laugh — “Ha, the goodbye didn’t take” — releases the tension for both of you. Ignoring it is how awkward conversations get stuck.

A friend of a friend at a birthday dinner

Oh — okay, we’re doing a handshake. Ha.

Flat reply

“Ha… yeah.”

You both study the menu like it’s homework.

Better reply

“Ha, I went handshake, you went hug. Let’s call it a hug-shake. Good to see you!”

They laugh: “Hug-shake. I’ll take it.”

Why it works: Say the weird part out loud so neither of you has to pretend.

2 of 4

Choose what happens next out loud

Awkward conversations drag when nobody knows the plan. Decide: “Guess we’re walking together,” or “I’m peeling off here.” Saying it out loud turns awkward conversations back into normal ones.

A neighbor you just said bye to, now at the same bus stop

Oh. You’re taking the 14 too?

Flat reply

“Yeah… ha.”

You both scroll your phones a foot apart for ten minutes.

Better reply

“Apparently! Okay, we’re officially waiting together. How’s the new puppy?”

They relax: “Don’t get me started. He ate a sock.”

Why it works: Saying the plan out loud ends the guessing about what happens next.

3 of 4

If it’s fixable, say it quickly

Spinach in teeth, an open zipper, a tag sticking out — if they can fix it right now, tell them in one quiet sentence. It only becomes one of those awkward conversations if you make a speech about it, or say nothing and let them find out later.

A coworker heading into a client meeting

Okay, wish me luck. Do I look okay?

Flat reply

“Totally. You look great.”

He walks in with the dry-cleaning tag still pinned to his collar.

Better reply

“Almost. Tag on your collar, left side. Okay, now you’re good.”

He pulls it off: “Wow. Thank you.”

Why it works: If they can fix it right now, one quick sentence saves them.

4 of 4

Move on to a normal topic

Once it’s named, changing the subject to something easy helps: their coffee, the weekend, the lake. Don’t circle back to apologize three more times. The faster you go back to normal, the faster awkward conversations end — for both of you.

A friend’s coworker at a barbecue

Oh — that’s actually my husband, not my dad.

Flat reply

“Oh my God, I’m so sorry. I didn’t mean he looks old, I just— I’m so embarrassed.”

Two minutes later, she’s the one reassuring you.

Better reply

“Oh no. Sorry! Okay, starting over. How do you two know Rachel?”

She shakes her head, smiling: “College. Rachel was my roommate.”

Why it works: One sorry, then a normal question. That’s how it ends.

Awkward conversations: what makes them worse

Pretending you didn’t see each other, which turns one awkward moment into weeks of awkward conversations.
Over-apologizing until the other person has to comfort you.
Asking a string of questions about a plan you weren’t invited to.
Staying silent side by side, both hoping the other one will speak.

Awkward conversations examples: what to say

These awkward conversations show up at work, with friends and with near-strangers. The better lines are short, light and move things along.

The moment	Say this	Avoid this
You said goodbye, then walked the same direction	“Ha, the goodbye didn’t take. Guess we’re walking together.”	Walking side by side in total silence
A coworker has food in his teeth before a pitch	“Quick thing: poppy seed, front tooth, left side. You’re good. Go crush it.”	Saying nothing and hoping nobody notices
A friend mentions a trip you weren’t invited to	“I’m not going this time, but that sounds great. Is the lake warm yet?”	“Wait, who else is going? When was this planned?”
You run into a teammate at another company’s interview	“I didn’t see you here if you didn’t see me. Good luck in there.”	Pretending to be on your phone
You call someone by the wrong name	“Sorry — Dana! I know that. My brain skipped.”	Avoiding their name for the rest of the year
You wave back at someone who was waving at the person behind you	(laughing) “That was for you, wasn’t it? Carry on.”	Turning it into a fake stretch

Why am I so awkward in conversation?

Feeling awkward in conversation often comes from watching yourself instead of the other person — replaying what you just said while they’re still talking. Awkward conversations feel longer from the inside than they look from the outside. Most people forget your stumble within minutes, especially if you laugh it off. The less you try to hide the awkward moment, the less awkward it becomes, and the more you look like a good conversationalist.

Awkward conversations: FAQ

How do you keep awkward conversations from getting worse?

Focus on the other person instead of yourself, ask about something they just said, and when a weird moment happens, name it lightly and move on. Awkward conversations usually get awkward because someone tried to pretend nothing happened.

How can I be less awkward in conversation?

Most awkward conversations start in your head. Stop scripting your next line while they’re talking. Listen, react, ask one follow-up. Let small pauses happen. If you stumble, laugh at it once — “Wow, words are hard today” — and keep going.

What do you say when things get awkward?

Say the obvious thing with a smile — “Well, that was awkward” — and then move straight to something normal, like a question about their day. Naming the moment once is enough — awkward conversations shrink the second someone acknowledges them.

Should I tell someone they have something in their teeth?

Yes, if they can fix it right now. Tell them quietly and plainly: “Quick thing — left front tooth.” Most people are grateful. It’s far less awkward than finding out after the meeting.

How do you recover after awkward conversations?

Next time you see them, act normal and friendly. If it was a real misstep, a short “Sorry about the other day — that came out wrong” is enough. Don’t keep revisiting it; replaying awkward conversations is what keeps them alive.

Meet Communicate Better

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