Humans are drawn to each other. As social beings, we find conversations to be one of the more enjoyable ways to connect, strengthen our relationships, and learn about the world. Yet conversations are not always fun. At one time or another, we’ve all found ourselves stuck in an awkward, difficult, or draining dialogue.
There are many reasons a conversation might go off track. You and your conversational partner might lack common interests. Maybe you’ve said something regrettable, or you’re stuck in a chat where you can’t get a word in edgewise.
Whatever the reason for the disconnect, awkward conversations can generate stress and discomfort.
Still, even the most stilted chats can become rewarding exchanges when you approach them in the right spirit, suggests Rob Kendall, a communication consultant, coach, and author of Watch Your Language. He recommends adjusting your expectations and being prepared with a few strategies for repairing (or exiting) an interaction when necessary.
Stress Source
You don’t know what to say. You’re speaking with someone you just met or with whom you have little in common. You can’t think of a single thing to talk about.
You feel uncomfortable with silence. When seconds pass without a word, your cortisol levels begin to rise. The more anxious you feel, the harder it can be to come up with a new topic.
You say something you regret. We all make conversational faux pas. Perhaps you inadvertently blurted something demeaning or derogatory. Or you disparaged something the other person values. You know you’re in the wrong, and you don’t know how to recover.
You discover that you and your conversational partner have opposing beliefs or perspectives. You express a view or opinion in a way that assumes the other person’s agreement. But then, to your surprise, they counter with a take that’s 180 degrees different. You freeze, unsure how to bridge the gap.
Your conversational partner keeps interrupting you. There’s a cartoon storm cloud forming over your head as the other person talks over you at length, rolling over all your contributions. They refuse to let you finish a sentence.
You’re misunderstanding each other. It’s clear from the other person’s responses that they aren’t grasping the points you’re trying to make — and your attempts to tune in to their perspective aren’t working either.
Your conversational partner is nosy — or oversharing. Someone you don’t know well asks about your family situation, childhood traumas, or religious or other deeply held beliefs. They might also be sharing more about their own story than you want to hear. Either way, it’s making you uneasy.
You can’t find a way to gracefully exit. You’re trying to end the conversation, but the other person keeps talking — and you aren’t sure how to exit without being rude.
Success Strategies
1) Let go of expectations. Not all conversations will be free-flowing or stress-free, Kendall notes. That doesn’t mean something is wrong.
“Conversation, by its very nature, is somewhat chaotic; it fluctuates,” he says. “You can never predict or predetermine what the other person is going to say or where the talk is going to go.”
2) Be curious. When we assume we know what someone is like or what they’re going to say, we close ourselves off to what we could learn if we were to simply ask them about themselves.
“Our preconceived ideas about the other person are probably the greatest obstacle to effective conversation,” says Kendall. “If we listen through the filter of our judgments and opinions, we are mostly confirming what we already know. This leaves little space for curiosity or discovery.”
3) Listen closely. “If I want the conversation to flourish,” Kendall says, “I give my full attention to what the other person is saying rather than thinking about what I’m going to say next. If I pay attention, then the chances are that whatever I say next is going to spontaneously be appropriate to the context.”
He recommends practicing the skill of active listening by tuning in to the other person’s words and nonverbal cues. (Find more tips for becoming a better listener at “5 Tips to Become a Better Listener.”)
4) Ask questions. When conversation falters, Kendall suggests asking open-ended questions. “[These] promote further conversation better than yes-or-no, binary ones. ‘What brought you to this party?’ or ‘What did you love about growing up here?’”
Pay attention to what your conversational partner shares about their likes and dislikes; these clues can guide your questions. “Who doesn’t appreciate somebody who takes an interest in their world?” Kendall asks.
5) Go with the flow, attentively. “The best conversation has a spontaneous flow to it, and you and your conversational partner adapt to the flow,” says Kendall. That means sensing how your interlocutor is reacting and then responding to the energy.
For example, maybe you see the other person’s eyes fall when you ask about their job but light up when they mention the basketball game they just watched. Follow that energy: Ask how they’re feeling about the next matchup, how they got into the sport, and which players they’re watching closely this season.
6) Apologize without explanations or excuses. If you say something that could have offended the other person, apologize without explanation or self-justification, Kendall suggests.
“Often when people apologize, they don’t really apologize; they give reasons for what they said. But if you just say, ‘That was deeply inappropriate, and I’m very sorry,’ you take the whole responsibility on yourself. People respect that.” (Learn more about sincere apologies at “4 Tips for Offering a Sincere and Meaningful Apology.”)
7) Acknowledge a clash of values. If you and your conversational partner are at loggerheads because of differing views, don’t simply plow on with the topic, Kendall says. Instead, you can say, “This is probably a conversation for another day.” And that signals that you want to move on.
8) Address oversharing. The same goes for issues such as oversharing or invasive questions. Kendall recommends politely addressing the problem rather than avoiding it in hopes the trouble will go away.
It can be easier to address these issues with someone you know. With someone you know less well, Kendall advises, take a calm approach and offer a concise statement. As a response to oversharing, you might say, “This is territory where I’m not too comfortable.”
9) Change the subject. “I know that requires quick thinking, and [that’s] somewhat clumsy to do midway through a conversation,” Kendall says. “But better the slight awkwardness of changing the topic than getting into an argument that isn’t going to go well.”
You can always pivot to a good question, he adds.
10) Keep tone in mind. Kendall emphasizes that maintaining a polite tone is crucial when navigating awkward or uncomfortable moments. A good conversation can be passionate and animated, but it’s important to remain respectful — even during heated discussions.
11) Say you’ve got to go. As a last resort, “it’s always perfectly acceptable to remove yourself from the conversation without any elaborate justification,” Kendall says. “It can be as simple as ‘I’m sorry, I’ve got something else I need to deal with’; ‘I need to speak to someone else’; or ‘I need to excuse myself for a moment.’”
It’s also OK to end with “Thanks for the chat — all the best to you.”
This article originally appeared as “Well, This Is Awkward . . .” in the November/December 2025 issue of Experience Life.
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