103 Conversation Starters to Keep Awkward Silences Away

Starting a conversation is almost like making friends with anxiety.

And finding the right conversation starters or icebreakers, so that things don’t get awkward, isn’t always the easiest. So let’s get rid of that stress, and make you a conversation-starting genius with insightful questions and good dialogue. 💪

Because becoming a confident person who knows exactly the best things to talk about, how to grow a deeper connection, and who can easily start interesting and entertaining discussions is something you are capable of. You should be able to go from a close friend to talking to a random stranger at a party, and know some great conversation starters, topics, and thought-provoking, good questions for a discussion.

I promise you can get good at conversing with others and be able to easily stay away from boring small talk. You can go deeper and grow in intimacy with your friends or partner and have so much more fun getting to know new people at work or even on a first date.

You’re not bad at it, you just need practice. And these good convo starters will help you get there!

---

Good Conversation Starters in This Article:

• Best Conversation Starters for Nearly Any Situation
• Interesting Topics to Talk About (That Won’t Bore Anyone)
• Conversation Starters for New People to Break the Ice Naturally
• Party Conversation Starters That Actually Work
• Conversation Starters for Dating That Go Beyond the Small Talk
• Conversation Starters for Friends for Better Yap
• Conversation Topics for Parents & Siblings to Bring You Even Closer
• Good Conversation Starters for Work That Aren’t Awkward
• Deep Conversation Starters for Meaningful Connection
• Questions for Keeping the Conversation Going

---

Best Conversation Starters for Nearly Situation

103 conversation starters to try! Break the ice, have fun, & dive deep with these topics to talk about so you can get to know someone or calm your nerves.

This list of conversation starter questions is now your new best friend.

1. So tell me about yourself.
2. What do you think about this get-together?
   {Or insert location, speaker, event, party, etc. that you’re both attending}?
3. If you were in charge of the playlist, which song would you play next?
4. Have you been on any nice trips recently?
5. Any fun plans for this year?
6. So how did you meet the host?
7. What was the last really good book you read?
8. How have things with your work been this year?
9. What’s a (hobby, pursuit, interest, etc.) you’ve taken up this year? 
10. What have you been learning or reading about lately?
    Follow-up question: Tell me more. In what way do you feel it’s changed your perspective?
11. Hey, I really like {insert their hairstyle, outfit, etc.}! 
    Quick Tip: Compliments are a powerful way to start a conversation, I’ve done it before. Use this if you want to quickly get rid of any walls, and make things more easy going. But just make sure the compliment is genuine!
12. So how many kids do you have? 
    Follow-up question: Could you tell me more? I’d love to hear all about them!
13. Hey, I heard about {insert trending topic}. What’s your opinion?
    Quick Tip: Make sure that any questions to start a conversation are non-controversial topics or events to keep things casual.

Next Step: Once you’ve gathered up some of your favorite conversation starters, here’s how to become a better conversationalist.

---

Interesting Topics to Talk About (That Won’t Bore Anyone)

I curated a list of some quirky and awesome question starters (from real people on Reddit) on interesting topics to talk about. So if you’ve been looking for topic starters that are legitimately good, then here are some great ideas for fun topics!

1. Talk about the weather but from a different angle: “Talking about weather is bad if it’s about, say, how much it is raining outside right now. Talking about weather can be fun if it’s about how there was flooding yesterday and three dogs survived by riding on the top of a horse, and one time a bunch of thieves tried to rob a Target at night but then there was a flood and they ended up on the roof waiting for a police helicopter to save them/arrest them, etc.” – Preposterous_punk
   Side Note: Agreed, I’ve heard some crazy weather stories, so if I can tie in cool things into something as average as the weather, then I think it can make a great conversation.
2. Talk about when the mundane gets crazy: “Again, everyone is familiar with the mundanity of the grocery store and DMV, and this is WHY they can be good topics, if something outside the norm happened. There doesn’t need to be a long explanation of the setting, the circumstances, or why what happened was unusual. You can just say, “that new grocery store on tenth? The staff all dress as clowns and speak in rhyme!” The context is common ground, but the specifics are unusual. Everyone can then discuss why on earth they would do that, whether that would make them more or less likely to shop there, and what other strange themed stores they’ve been to.” – Preposterous_punk
3. Trending or talk-worthy food topics: “What works in this topic depends on what the people present care about —if everyone likes cooking, trading recipes is great! Otherwise, not so much. But most people enjoy talking about food extremes — unusual dishes, particularly delicious food (especially sweets) or funny/horrific cooking disasters. Be careful with gross-out stuff though; it can be super-fun for some people and horrible for others.” – Preposterous_punk
4. Non-academic or work successes: “What is your biggest non-academic, non work-related accomplishment?” – Sushideception
5. “What will always be funny to you?” – Sushideception
6. Reliving one day in your life with no changes:“If you could go back and relive one day in your life without changing anything about it, which day would you revisit?” – Sushideception
7. The season you’d live in eternally: “If seasons never changed, which would you most like to live in eternally?” – Sushideception
8. Smallest thing you’re most grateful for:“What is the smallest thing for which you are grateful?” – Sushideception

Related: 250 Truth or Dare Questions

---

Conversation Starters for New People to Break the Ice Naturally

1. So what brought you to this event (or location)?
2. So how do you know {insert mutual friend’s name}?
3. What’s your workplace like?
4. What’s something you’ve been working on this year?
5. Follow-up question: Tell more, what about {insert interest, passion, etc.}; why do you want to pursue it?
6. Tell me about your family! What are they like?
   Quick Tip: This one is simple, but it’s very helpful. Don’t underestimate this conversation starter; people love talking about the people they love.
7. So what are you really passionate about right now?
8. What’s something you read {or watched} recently that’s really got you thinking?
9. Any favorite {shows, podcasts, etc.} you’d recommend starting?
10. Do you have any fun plans for this month?
11. Are there any big or small things you’ve been enjoying working on lately?

---

Party Conversation Starters That Actually Work

1. So how did you get to know {name of mutual friend}?
2. What do you like about your work? I’d love to know more about it.
3. The holidays {or specific season} is coming up. Anything you’re personally looking forward to?
4. What’s something you learned recently that you think is pretty cool?
5. Any new interests you’ve been looking into {or pursuing} lately?
6. What’s something you’ve been reading or listening to that’s really got you thinking?
7. What are your thoughts on {insert relevant, popular, and non-controversial topic}?
8. Is there something you want to work on in your life this year?

Related: 150 Best “Never Have I Ever” Questions

---

Conversation Starters for Dating That Go Beyond the Small Talk

1. What’s something you want to do, or try, but you’re a bit too scared?
2. Are you working towards any big or small goals right now?
3. How do you {like, feel, or think} about your job position {or workspace}?
4. What’s something you’re learning right now or want to learn?
5. So what kind of places have you visited this year? 
   Follow-up question: Tell me about it, what did you think?
6. So where are you from originally? 
   Follow-up question: Tell me more about {insert their hometown, country, etc.}
7. Tell me more about your family, what are they like?
8. Is there anything you’re really passionate about?

---

Conversation Starters for Friends for Better Yap

1. What’s something new you started doing this month?
2. What are some of your favorite ways to do self-care?
3. Are you still pursuing {passion, hobby, etc.}? 
   Follow-up question: How is it going?
4. How are your {kid(s), spouse, family member} doing?
5. How’s the situation with your {friend or family member} going?
6. How has your work life been lately?
   Follow-up question: Do you feel that you’re thriving in it?
7. Has anything changed at your workplace lately?
   Follow-up question: Are there any projects you’ve liked working on?
8. What are some ways I can be a better friend to you?
9. What’s something that’s been on your mind lately, that you can’t stop thinking about?
10. Hey remember {insert person’s name}? What are they even up to now?
11. Have you learned any random fun facts that blew your mind lately?

---

Conversation Topics for Parents & Siblings to Bring You Even Closer

These topics will help you to connect with your parents & siblings more deeply:

1. How have you been since the last time we talked?
2. What kind of upcoming plans do you have ready for {month, year, holiday, season, family get-together, etc.}?
3. Hey, how’s your friend, {friend’s name}, doing lately?
4. Hey, how’s {family member} doing? I haven’t heard about them lately.
5. How did your trip to {location} go?
6. How have you guys been doing at your workplace lately?
7. Hey, I’m planning on going to {inset location}. I know you guys went there before; any tips or advice on what to do or not do?
8. I’m planning on doing {event, life change, sport, etc.}, and I know you guys did that in the past. Any advice or tips?
9. How’s your relationship with {person’s name} been lately?
10. What do you think everyone in our family will probably be doing in {5, 10, 20 years, etc.} from now?
11. Hey, do you have a {self-care, morning, night, etc.} routine right now?
    Follow-up question: What do you do? I want to make my own routine for that.
12. What’s one of your favorite memories from our childhood?
13. How’s that {project, passion, etc.} been going?
14. What’s something you had wanted to tell me when we were kids?
    Follow-up question: Why did you decide not to?

Related: 170 Would You Rather Questions

---

Good Conversation Starters for Work That Aren’t Awkward

1. What do you like to do immediately right after work?
2. Is there a project, or a part of your work, that you’re really enjoying right now?
3. What’s your favorite part {or not favorite part} about networking?
4. What’s a skill you’d like to improve on?
5. Have you been reading any books that have been helping you with your work and/or mindset?
6. Are there any podcasts or audiobooks you listen to on your commute to work?

---

Deep Conversation Starters for Meaningful Connection

Here’s a great list of deep conversation starters to help you get to know someone better:

1. How are you, really?
2. How have things really been between you and {insert family member name, friend, etc.}?
3. Hey, is there anything in your life you need help or advice on?
4. What are some things you really want, and need, to accomplish this year?
5. Who’s been the biggest influence in your life so far?
6. What scares {or excites} you the most about the future?
7. How have your views {or priorities} changed in the last {year, 5 years, 10 years, etc.}?
8. If you could change 3 things in your life this year, what would they be? Why?
9. What’s a bucket list idea you’ve started pursuing this year?

---

Questions for Keeping the Conversation Going

If you’re ever feeling kinda stuck in a conversation and you’re not liking the awkward silence, then I’ve got you.

Use these great questions to keep the conversation moving forward:

1. How did you feel when {insert event} happened? Did it change your {belief, response, thinking, values, etc.}?
2. Tell me more about your experience with {event}. What did you {learn, do, think, etc.}?
3. Tell me more about this person. How have they changed your {thinking, values, etc.}?
4. Could you tell me more about {location}? I’d love to visit someday!
5. So what is it about {topic the person is discussing & interested in} that you really like? I’d love to know more!
6. So how did that {book, show, podcast, etc.} change how you see {insert topic}?
7. So what else have you been learning lately?
8. What else has been happening for you this year? Anything crazy or interesting?
9. What would you change about {the experience or event they brought up}?

---

I really do hope that all of these tips and at least one convo starter from this list helped you out! I know how stressful it can be, so I wanted to create a list of conversations starters to make things a bit easier for you.

So take a few of these with you into real life interactions, ask some great questions, and start sparking deeper talks and funny conversations!

PS – Let me know how it goes! 🙂