Ever walked away from a conversation and thought, “Well, that was weird”?
Maybe the other person seemed uncomfortable, or the chat just didn’t flow like you hoped. Awkward conversations can happen for all kinds of reasons, but sometimes, the problem isn’t the other person — it’s what you’re saying. If your chats tend to feel off, here are some of the conversational tools you might be using that could be making things awkward.
1. “So… what else is new?”
When a conversation starts running out of steam, this question often gets thrown in as a last-ditch effort to keep it going. The problem is, it puts all the pressure on the other person to come up with something interesting to say, which can lead to an awkward pause. If they don’t have anything exciting to share, the conversation just fizzles out.
Instead of a vague “what’s new?” try bringing up something specific, like “How’s that project you were working on?” or “Have you watched anything good lately?” A specific question gives them an easy way to engage, which keeps the conversation flowing naturally.
2. “You look tired.”
Even if you mean well, this one never lands right. No one likes being told they look exhausted, and unless you’re their doctor, it’s not really necessary to point out. It might make them feel self-conscious or even annoyed, especially if they weren’t feeling tired until you mentioned it.
If you’re concerned, ask, “How have you been feeling lately?” or just let them bring it up if they want to. No one ever responded to “You look tired” with a cheerful, “Thanks for noticing!” so it’s best to avoid saying it at all.
3. “Not to be rude, but…”
Nothing good ever follows this sentence. If you have to preface something with “not to be rude,” there’s a good chance it’s about to sound rude. It instantly makes people defensive, even before you’ve finished what you’re saying.
If you need to bring up something uncomfortable, just be direct but kind. Saying, “I had a different perspective on that” or “Can I be honest about something?” is a much better way to get your point across without making things tense.
4. “Wow, you’ve lost weight!”
It might sound like a compliment, but commenting on someone’s weight — whether they’ve lost or gained — can make things awkward fast. You don’t know the reason behind the change, and it could be tied to something they don’t want to talk about. What you see as a compliment might remind them of something stressful.
If you want to compliment someone, focus on something neutral, like “You look great” or “That outfit really suits you.” That way, it doesn’t come across as an unexpected deep dive into their personal life.
5. “You wouldn’t believe what happened to me…”
Jumping straight into a personal story without any lead-up can make the conversation feel one-sided. If the other person was mid-thought or trying to share something, it can feel like you’re ignoring them completely. It also makes it seem like you’re not interested in what they have to say.
Instead, try easing into it with, “That reminds me of something wild that happened — want to hear?” That way, the other person gets a chance to actually opt into the conversation instead of feeling like they’ve just been steamrolled.
6. “I don’t really like that.”
There’s nothing wrong with having opinions, but shutting something down completely can make things awkward, especially if the other person was excited about it. If they were sharing something they love, hearing a blunt “I don’t like that” can feel dismissive or even a bit harsh.
Instead of a flat-out rejection, try, “It’s not really my thing, but I can see why you like it.” That way, you’re keeping the conversation open rather than killing their enthusiasm, and you’re showing that you respect their interests even if you don’t share them.
7. “I hate small talk.”
People say this to sound deep or interesting, but it usually just makes things more uncomfortable. Small talk is how conversations naturally start; it’s a warm-up, not a waste of time. Acting like it’s beneath you can make the other person feel awkward or self-conscious.
If you don’t like small talk, steer the conversation in a different direction instead of announcing it. Ask an interesting question, bring up something recent, or get them talking about something they’re passionate about. That way, the chat stays engaging without making anyone feel weird.
8. “I heard something about you…”
Unless you’re about to share something they’ll be excited to hear, this phrase usually makes people defensive. It immediately puts them on edge, wondering what’s coming next. If it’s gossip or something personal, it can feel invasive or even confrontational.
If you have something to say, just say it directly and in a way that doesn’t put them on the spot. And if it’s just gossip? Probably best to skip it altogether unless you want to make things awkward fast.
9. “When are you having kids?”
This might seem like an innocent question, but for a lot of people, it’s a personal and even painful topic. Not everyone wants kids, and some people are struggling with fertility or other issues they don’t want to discuss. Asking can bring up emotions they weren’t expecting to deal with in casual conversation.
If someone wants to talk about their family plans, they will. Until then, it’s best to avoid making it a conversation topic. You never know what someone might be dealing with behind the scenes.
10. “Remember when you did that embarrassing thing?”
Bringing up an old embarrassing moment might seem funny to you, but for the person involved, it might not be something they want to relive, especially in front of other people. What’s hilarious to one person can be mortifying to another.
If you’re unsure whether they find it funny too, it’s best to leave the past in the past. No one wants to be reminded of their cringiest moments at random, especially when they didn’t ask for it.
11. “At least it’s not as bad as…”
When someone shares something tough, responding with “At least…” can feel dismissive. Even if you mean well, it can make them feel like their feelings aren’t valid. It might come across like you’re downplaying what they’re going through.
Instead, try something simple like, “That sounds tough. How are you feeling about it?” That way, they know you’re actually listening, not just trying to make the problem seem smaller.
12. “I’m just brutally honest.”
People who say this usually use it as an excuse to be rude. Honesty is important, but if you’re regularly making people uncomfortable, it might be more about delivery than truth. Just because something is true doesn’t mean it needs to be said bluntly.
You can be honest without being harsh. If you need to give constructive feedback, phrasing it with care makes a huge difference. People are much more likely to listen when they don’t feel attacked.
13. “Awkward…”
Pointing out awkwardness only makes it worse. If a silence falls or a joke doesn’t land, calling it out makes everyone more uncomfortable. The moment might have passed unnoticed, but now it’s a focal point.
Instead of saying it, just move the conversation along. A little silence or a weird moment isn’t the end of the world — unless you draw attention to it.
