We all have at least one person we don’t like in our life. Instead of being rude or cold, use our conversation starters to survive your interactions…and maybe, just maybe, you will learn something that helps you like them more.  

How Do I Have a Conversation With Someone I Don’t Like?

The best way to converse with someone you don’t like is to set aside all negative feelings like judgment or anger. Every person deserves to be treated with dignity, regardless of how you feel about them. 

In other words, when you talk to someone you don’t like, extend kindness with a calm mind and a heart free of judgment. Replace those negative feelings with curiosity.

Curiosity can make you more charismatic without having to pretend or be fake.

Is your difficult person a coworker? Vanessa deeply delves into how to deal with difficult people at work.

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Fill-in-the-Blank Conversation Starters

The best conversation starters consider the context of the situation and the person you’re talking to. Instead of memorizing one-liner conversation starters, think about how to engage with this person genuinely based on things you’ve been thinking about or experiencing. These fill-in-the-blank starters will give you a framework to avoid awkward silences.  

  1. I’m wondering if I could get your opinion on ____? Whether trying to choose a new lawn mower or thinking about a new career, people love to give their advice, so why not ask for it? You can follow up with them later (if you take their advice) and tell them how your new self-propelled 56-volt battery-operated lawn mower has changed your life. 
  2. I just tried ___ for the first time, and I loved it. Have you ever tried that? It doesn’t matter whether you just tried a new brand of cereal or just tried bungee jumping! Think of everything from the mundane to the spectacular. You can look for things you share in common and discover whether they like to try new things or prefer to stick to what’s tried and true. Follow-up questions could be, “Do you like to try new things?” or, “What’s something new that you’ve tried recently?” 
  3. How is ___ going? Think about what they shared with you in the past and ask about it again. It shows you’re listening and is an easy start to a conversation. Did they mention a new project or classes their daughter was starting? Ask them how it’s going and include follow-up questions like, “Is that as stressful/fun as it sounds!?”, “Tell me more about what that’s like.”
  4. Did you see ___ (insert latest viral video)? Make sure to pick something that isn’t political or religious, preferably funny. This can provide a safe topic to laugh over. Follow-up with asking about what influencers they like the most. 
  5. How is ____ (the person you share a connection with)? If you feel uncomfortable and neither of you wants to talk about your thoughts or feelings, introduce the middle man. Asking about your shared connection is usually a safe topic.

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If You Don’t Have Anything Nice to Say, Say This

Don’t attempt deep conversations when someone gets under your skin. Keep things light, and avoid topics that could result in emotional carnage. 

  1. How are things going on your latest work project? Suitable for a coworker or almost anyone, this question is reasonably safe territory to get them talking about the highs or lows of work. 
  2. I heard things at your job have been pretty crazy. How’s that going? This question demonstrates interest in what has been challenging for them lately. If they stay home to care for the kids, adjust this question to replace “job” with “home.”
  3. Have you read anything this year that you’d recommend? I’m looking for something new to read. This question is a classic for a reason, it’s neutral ground, and most people will be happy to share what they’ve been reading. If they don’t read, ask them if they have a favorite podcast or movie.
  4. That ___ looks like it tastes amazing! Is it a favorite family recipe? Ask follow-up questions like, “Do you like to cook?”, “What’s your go-to food when you don’t feel like cooking?”, “Did your family cook a big holiday meal growing up?”
  5. Do you have any fun vacations planned? If they say no, ask if they like to travel or if they prefer to spend their vacation time locally. If they choose to stay local, ask for recommendations of fun places to go. If they like to travel, ask what some of their favorite travel spots are. 
  6. Tell me your best joke. People love to laugh, and asking for a joke usually gets a great response. Have a trick or two ready to share, and cut some of the tension with shared laughter. Pro Tip: If you’re concerned about them telling an offensive joke, specify you want a clean or family-friendly joke. 
  7. How did you become a ___? Ask this question to learn about their story and show interest in who they are. 
  8. What are you looking forward to this week? This conversation starter has the potential to spark a fun conversation. 
  9. What’s something you could talk about for hours? Follow this up by asking how they first got interested in this topic. 
  10. What’s your favorite app at the moment? While this sounds like a light question, it could reveal something about their personality. Maybe their favorite app is Marco Polo so they can stay connected with their daughter overseas, or they love Robinhood because they’re obsessed with investments. These little details reveal the humanity of the other person. 

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Unlock the Secrets of Charisma

Control and leverage the tiny signals you’re sending—from your stance and facial expressions to your word choice and vocal tone—to improve your personal and professional relationships.

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Conversation Starters for Difficult Family Relationships

Family can be complicated. If you have family members, you don’t like them. 

  1. What was the worst job you’ve ever had? When you want to keep the topic far from any family drama, ask questions where they can share a story.
  2. What family memories do you wish I’d gotten to know? Exploring those positive memories can keep the conversation calm.
  3. I love how you’ve decorated your home. What was your inspiration? Show interest in their life and compliment something that won’t turn into a contentious topic. 
  4. I’ve noticed you’ve been ___ (insert recent hobby or interest). I’d love to learn more about it. What do you love most about it? Follow up with questions about whether it’s been hard to understand, whether they could teach you, and how it makes them feel. 
  5. What are your first memories of me? You may be surprised to discover their earliest memories of you are more loving than you imagined. 

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Conversation Starters to Be More Open-Minded

Shift your mindset to believe that complex and unlikeable people are in your life for a reason. What can you learn from interacting with them about yourself or the world? 

As you listen, look for the heart of their words and be willing to shift the ideas you’ve formed about them. They may be an entirely different person than you realized. 

  1. What’s it like being a ____ (Insert occupation)? Follow-up by saying, “That sounds like it would be very challenging! What do you feel most people don’t realize about your job?” Don’t leave out stay-at-home moms/dads. You can ask them this same question, but remove the word “job” or “occupation.” 
  2. What do you mean by ____? When it comes to people, you don’t like. They probably hold opposing beliefs. Instead of being angry or dismissing their views, ask detailed questions to understand their beliefs better. They may be using inflammatory language, but when you dig deeper, their definitions may be different than yours, causing unnecessary miscommunication.  
  3. I’m interested in your perspective. What do you think about ____? Instead of employing accusative or sarcastic language, you are taking the humble stance and essentially signaling to the other person, “Hey, I think you have something important to say on this subject. I see you, and I want to hear you.” But be careful you don’t start down this path if you’re going to get heated and angry. Practice with less controversial subjects to build your emotional intelligence.  
  4. What impact do you want to have on other people? This question can be eye-opening and shift your view of the other person. 
  5. What do you appreciate most about your life? This question opens the door for a quick response or even a deeper discussion about a pivotal moment in their life. You might learn about a loss that caused them to value the small things or a chronic illness, causing them to be grateful for any moment free of pain.  

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Questions to Protect and Deflect

Some people seem intent on asking probing and even inappropriate questions. If this is what you’re facing, your goal is to protect and deflect. Just because you’ve chosen a stance of neutral kindness does not mean you have to answer questions that make you feel uncomfortable. 

When the barrage comes, try these techniques to redirect the conversation politely. 

  1. The Parrot

The key to this technique is to turn the question—whatever it may be—back on the other person. 

Say they ask who you’re voting for in the next election; politics is the last thing you want to discuss. Try saying:

“Oh yes, everyone has strong feelings about the election. I’d love to hear your perspective on it before I head back to my desk. I only have a couple of minutes, though!”

Build your response: Acknowledge the question + redirect to the other person with the same question + place a time perimeter on the conversation. 

  1. The Deflector

The next technique we have is The Deflector, which takes a probing question and answers it with another question. You can thank good old Socrates for this; he used it as a method of education. On the other hand, you are using it as a conversation starter to deflect uncomfortable or difficult questions.

Answer a problematic question by asking one of these:

  • Why is that a priority for you?
  • What makes that important to you?
  • Do you feel that’s an appropriate question to ask me?
  • What do you think?
  1. The Politician 

Use this conversation starter to change the topic. It may seem unnatural or uncomfortable, but try it out, and you’ll be surprised at how effective it can be. 

Let’s say someone asks you the dreaded, “When are you going to settle down and get married finally?” 

Instead of answering this offensive question, try, “You know, I’ve heard fewer people are getting married and having kids. That reminds me of another trend! Have you noticed people are wearing hoodies under their blazers? What do you think, cool or gross?”

Build your response: Vague reply about the general topic but not the question + random connection to another topic + question to start a new conversation.

  1. The Pollyanna 

If someone asks you a snide or sarcastic question, respond with an overzealous positivity that would make even Pollyanna envious. 

Say your least favorite Aunt asks (again), “When are you going to get a real job?” try responding with something like: 

*Laugh to diffuse your annoyance* “I know! You’d think I’d have figured out my life by now, but I’ve been learning some amazing lessons at my job that are preparing me for the next stage in my career. What about you? Did you know what you wanted to do right away? How did you get to where you are today?”

Build your response: Positive response with humor + a positive spin on what they see as unfavorable + ask questions about their story. 

Disclaimer: Only use this if you can do it genuinely! Choose a different response technique if your Pollyanna is likely to come off as sarcastic. 

  1. The Clarifier 

Sometimes people ask insensitive or hurtful questions without meaning to. Instead of stumbling over your response or ignoring how it made you feel, meet these questions head-on by rephrasing and clarifying. 

When someone asks, “Do you have a family?” You can say, “I think what you’re asking is if I have any children? No, I don’t. Do you have children?”

What you’ve done here is taken away the ambiguity, refuse to absorb any shame from the question, and quickly bounce the question back to their side to answer. 

Spark this into a conversation by asking follow-up questions about their kids. 

Build your response: I think you mean… + answer the question you’ve clarified + pass the question back.

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Communicating With Difficult People Comes Down to 3 Things

#1 Avoid Anger and Annoyance

According to a study by the University of Sussex, anger hampers clear thinking, and the person you are angry with will mirror that anger. 

You may be thinking, “But I’m not angry! I don’t like them.” 

According to reputable sources, disappointment, frustration, rejection, and fear can all be sources of anger. Unregulated, those emotions cause actual changes to your brain and have the power to disrupt your cardiovascular system, immune system, and digestive system. You can track the science from NICABM in this infographic.

Walking around with anger and annoyance towards people you don’t like reduces your mental and physical well-being while eroding your ability to connect with others, including those you want. 

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#2 Set Your Goal

As strange as it may sound, you need a clear understanding of what you want to accomplish during your interactions with the person you don’t like. Setting a goal removes you from a defensive stance against a perceived enemy.

Start by asking yourself some questions:

  • What can I learn from this person? Do they have a different experience or perspective on life that I don’t understand? Even if you don’t like their viewpoint, broadening your worldview can only strengthen you as a person. 
  • Will it hurt someone I care about if I’m rude to this person? How can I focus on the person I care about rather than this person I dislike? 
  • How can I be polite while still respecting myself and my boundaries? What am I willing to overlook, and what are non-negotiables for me. What is my exit plan if they violate my non-negotiables?
  • Do we share anything in common, even if it’s minimal? How can I identify those common areas?
  • Am I willing to prioritize kindness and my growth as a person over a need to prove this person wrong? How can I demonstrate kindness and civility, even if the other person is rude or annoying? 

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#3 Prepare to Interact

  • When you see a person you don’t like, look at them without judgment.
  • In your mind, wish this person well. It only takes 2 seconds!
  • If you have a spiritual practice, you can say a quick prayer of blessing for this person.
  • As you talk to them, avoid thinking about past grievances. Be present at the moment.
  • Be curious. Start observing their nonverbal cues to understand what they may be thinking or feeling. Observe this impartially, like a scientist gathering information. As you pick up on their nonverbals, you may discover things that surprise you or cause you to feel compassion. 
  • Look for likable qualities. While you may not agree with their politics or work ethic, look for positive traits. You may dislike their political party, but maybe their stance comes from a deep desire to protect their family. You can agree that’s an admirable quality, even if you can’t agree with their methods or beliefs. Understanding what drives their actions may reveal positive attributes you were missing.  
  • Pay attention to your nonverbals too! Avoid communicating hostility or disinterest by looking around while talking, sighing, or crossing your arms

If you find ending a conversation even more alarming than starting one, check out our guide on How To Get Someone To Stop Talking To You, Nicely.

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