Be Memorable with Awesome Conversation Starters

An awesome conversation starter is guaranteed to make you more interesting, attractive, and memorable. Whether in a social setting, or business setting, using the best ice breaker questions will allow you to connect with people on a more meaningful level. Your lack of meaningful relationships can stem from your lack of meaningful conversations. As a result, engaging in deeper conversations is the best way to develop relationships with people. An awesome conversation starter will make you stand out from the mass of boring people that ask the same stupid introductory questions.

How do you typically start a conversation? I’m guessing it starts with:

“How are you?”

“What do you do?” 

“Where are you from?”

“How much do you bench, bro?” You lead with this, right? Or is it just me?  

These questions have their place but if you want to stand out, be more interesting to others, or develop deeper connections with people then be different! Lighten things up, get creative and stand out from the crowd with great ice breaker questions.

It’s no mystery why people don’t remember your names and potential customers don’t reply to your messages. You’re not asking good questions! Start strong by using an awesome conversation starter! Make your ice breaker question funny, playful, or thought-provoking.

Adam Gottesfeld teaches his students to get responses from high-level executives, celebrities, famous entrepreneurs, etc. by asking them a concise, thought-provoking question. He challenges his students to do this via cold calling or cold e-mailing but the use cases are interchangeable.

This is a real-life example of one of the best ice breaker questions (not so much of a question but a statement) I’ve ever heard: “So, tell me how you want me to remember you.” A friend introduced me to this person and this is what she led with. Being conditioned to the normal sequence of questions of an initial conversation, I was shocked and speechless. I stumbled over my own words and couldn’t even give a response. This was three years ago and I still remember the interaction clear as day. Wouldn’t you like to be this memorable? How would it feel if someone you met once three years ago still remembers your name?

Examples of Awesome Conversation Starters

1. What’s your story?

2. Tell me how you want me to remember you.

3. What are you working on that really excites you?

4. How do you know the host?

5. Have you been to an event like this before?

6. What do you think of this venue?

7. What global issue do you wish you could solve?

8. What brings you to this event?

9. Do you have any travel plans? Where? When?

10. What place have you always wanted to travel to?

11. What book are you currently reading?

12. What is your favorite book?

13. Who inspires you? Who do you aspire to be like?

14. Tell me something you believe in that very few others agree with?

15. What is one of your guilty pleasures?

16. What is your go-to drink?

17. If you were to have a destination wedding, where would it be?

18. What’s your favorite [curse] word?

19. What do you fear more? Zombies, artificial intelligence, or Donald Trump?

20. Who do you think would win in a fight? Miley Cyrus or Nicki Minaj?

21. Justin Bieber, Charlie Sheen, Harry Potter. You have to sleep with one, marry one, kill one. Go! 

22. How do you deal with awkward silences?

23. What is your most embarrassing moment?

24. Tell me the best/worst pick-up line you’ve ever heard?

25. What are some non-profit organizations or charities you are most passionate about?

26. What would your last meal be?

27. What would your stripper name be?

28. If you were given $1 million but had to spend it in one day, how would you spend it?

29. What is one goal you’d like to accomplish during your lifetime?

30. If you only had two weeks to live, what would you do?

31. What is a hidden talent of yours very few people know about?

32. If you could put up a billboard, where would you put it, and what would it say?

33. If a genie granted you three wishes, what would they be?

34. If you could be a professional athlete, what sport would you play?

35. Dogs or cats?

36. Do you think chivalry is dead?

37. What is the best compliment you ever received?

38. Tell me one thing you really like about yourself?

39. What is one thing you’d like to change about yourself?

40. If you were given a time machine, what time period would you go to?

41. Pie or cake?

42. Tell me about your worst date.

43. Would you call yourself an introvert or extrovert?

44. What does your typical Friday night look like?

45. What do you like to do outside of work?

46. What is your favorite movie? Actor/Actress?

47. Who was your childhood hero?

48. What app do you use the most?

49. If I were to check your internet search history, what would I find?

50. What is one skill you feel every person should have?

51. What is the best/worst gift you’ve ever received?

52. How would your friends describe you?

Using “Tell me” is extremely powerful. You are not asking for permission for them to answer. You are commanding them to give you a response. Using “Tell me” perceives you as a confident person. 

If you are uncomfortable around people or get anxiety about what to say next then try to follow up your question with another question. Make it about the other person. And the most important thing to remember is to ask open-ended questions. This will maintain the conversation and keep the other person talking. A lot of people don’t care what you have to say anyway.

If possible, be like David Caruso in Jade. 

Not so awesome conversation starters

• What do you do?

• How are you?

• Where are you from?

• How is your day going?

Seriously, stop using these conversation starters. Everyone uses them. Be different from everyone else. A great ice breaker may sound uncomfortable but that is natural since you’ve been using the same boring conversation starters. You might think these are useless but I assure you that they work. If you approach someone who’s constantly bombarded by people (beautiful women, high-level executives, etc.) wanting their attention then leading with a unique, thought-provoking question will surely make you stand out.

Alternatives to your not so awesome conversation starters

“What do you do?”

1. How did you get into your line of work?

2. Why did you choose your line of work?

3. What do you like most about your job?

4. What is your dream job?

5. Any books relevant to your field that you recommend?

6. Who are some thought leaders that you follow on social media?

7. If money wasn’t an issue, what would you be doing?

8. What side projects outside of work are you working on?

9. What is the biggest challenge you are currently tackling at work?

10. What does your ideal work environment look like?

Where are you from?

1. What was your favorite dish growing up as a child?

2. Have you tried replicating any of your mom’s cooking at home?

3. What’s a fun fact about your hometown?

4. How are the [their hometown sports team] doing?

5. If I were to visit your hometown, what would you recommend I do?

6. What was your favorite childhood movie?

7. What were you like in high school?

8. What did you want to be when you were growing up?

How are you?/How is your day going?

1. What’s the most exciting/interesting thing that’s happened today/this week/this month?

2. What do you think about [non-political current event]?

3. Where is your favorite place to get coffee?

4. Have you been to [new local restaurant]?

5. Where is your favorite happy hour spot?

6. What are your plans for the upcoming week/weekend?

Above all, the best ice breaker questions are a combination of what you say and more importantly, how you say it. 93% of conversations are non-verbal, 55% of it being body language, 38% of it being the way you say it, and 7% consisting of the actual words. Context is crucial. You can’t just walk up to a complete stranger and say, “Hi, tell me how you want me to remember you.”

An awesome conversation starter will make you stand out from the crowd of people that are clawing for the attention of others. Arming yourself with great ice breaker questions turns the focus to the other person and makes them do all the talking. Probing into what people are working on and passionate about makes YOU all the more interesting. As it goes, people love to talk about themselves.


  1. Love this post. I have social anxiety and tend to start all my conversations with a stutter, a stumble and a blank look in my So this is helpful. xoxo

  2. The questions are very apt for those situations and are real ice-breakers. I’m copying them on to my sticky notes so I could memorize them.

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