40 Insanely Creative Ways to Start a Conversation (For Any Social Situation)

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Last Updated on January 27, 2021

Have you ever been in a certain social situation where you needed to have a robust conversation with someone but didn’t exactly know how to begin? Don’t fret if you have, because you’re not alone. And if you haven’t, the chances are that you’re not meeting new people, which is a bad thing for your social capital.

While ending a conversation is easy, starting one requires a bit of creativity on your part.

First up, you must define the relationship that exists between you and the other person. That will help you to settle on the most relevant questions to ask. After that, go for questions that are both deep and interesting; not the kind that require one-line replies.

The following are some of the most creative conversation starter tips and tricks that you can use in most social situations.

10 Conversation Starter Tips

1. Start with the person’s name…

Mentioning the other person’s name is an effective way of encouraging intimacy in a conversation.

2. …Then repeat the name often

Don’t just mention their name at the start of a conversation, repeat it frequently enough throughout the conversation.

3. Discuss topical issues

What are the notable things that are currently taking place in your country? Is the country hit by industrial strikes, bad weather, or a famous death? These can be excellent conversation starters.

4. Make and maintain eye contact

Eye contact is an indication that you’re a good listener. It’s a great way to start a conversation and keep the other person engaged.

5. Wear the right facial expression

Another excellent way to start a conversation and keep it going is to put on appropriate facial expression. So, feel free to laugh at a funny joke or smile at a cute compliment.

6. Make use of gestures

Relationship experts claim that a woman is likely interested in a man if she fidgets with her hair, fingers, or eyebrows. Wouldn’t it be nice to let him know straight on that you’re into him?

7. Distance matters

Keep a close distance before starting a conversation. Of course, the distance shouldn’t be too close for comfort.

8. Make a genuine compliment

There must be something about the person that stands out. Mentioning this at the start of a conversation is a perfect way to seize their attention. Just ensure it’s an honest compliment and not mere flattery.

9. Answer a question with another question

Although this may sound impolite, it’s a creative way of holding the other person’s interest in a conversation.

10. Interact often

A healthy conversation shouldn’t be a question-and-answer session but an occasion for both parties to interact. So, feel free to ask the questions but also help the other person develop their response.

30 Conversation Starter Questions

1. I’m (Tom, James, etc.), you are? /what about you?

If you’re meeting a person for the first time, you’d naturally introduce yourself and then ask them to do the same. It’s a traditional trick of starting a conversation.

2. Do you like this place?

A very important question to ask at the beginning of a conversation, especially if you’re on your first date. If they don’t like the place, find a better venue immediately.

3. Tell me about yourself!

This is one of the most popular conversation starters that applies to nearly all social situations. When you pose this question, you allow the other person to share with you whatever they feel comfortable disclosing. They might choose to talk about their family, work and career, personal interests, etc. It’s all up to them.

4. Tell me more about yourself!

This question normally comes after ‘tell me about yourself.’ It means that although you’re happy the other person has shared a bit about their personal life, career, or interests, you’re still not satisfied with the answer. So, this question pretty much gets them to share other details that they may have omitted, either by accident or design.

5. What three words best describe you?

When you’re trying to avoid general details about the other person’s life, this is the perfect question to ask.

6. What’s your story?

This is a creative way of inviting someone to talk about the most exciting things in their life.

7. What are your strengths?

The answer should be relevant to the occasion. For instance, a job interviewee cannot list their strengths as ‘fun’ and ‘romantic.’

8. What are your weaknesses?

Some people may lie about their weaknesses, especially if they find those weaknesses embarrassing. But this question can still break the ice and keep the conversation flowing.

9. What’s your biggest regret?

Although the question may be uncomfortable, most people are happy to share the things they’re deeply remorseful for.

10. What do you do for a living?

This is a simple and direct question that seeks to establish the other person’s line of work.

11. Are you in school or working?

Some people may find the question ‘what do you do for a living’ somewhat impolite and intrusive. As such, you might consider this question instead. The question is also ideal when the person you’re meeting is relatively young and might still be in college or recently graduated.

12. What does your typical day look like?

A creative way to know how the person spends their day.

13. Are you an early bird or a late owl?

Generally, most employed people are early birds, whereas students are late owls. But the answer might go either way, so ensure the other person is a bit detailed in their response.

14. What’s your idea of a perfect weekend?

Asking this question will let you know whether the other person is an indoor or outdoor type.

15. What’s the most exciting thing you’ve done lately?

You want to know how adventurous or ambitious they are.

16. What turns you on?

Although this question usually carries sexual connotations, it might as well be asked to find out what makes the other person happy or enthusiastic.

17. What turns you off?

Pretty much the opposite of ‘what turns you on?’

18. Do you have a pet peeve?

A more decent way of asking, ‘what turns you off?’

19. Do you have phobias?

We all have that one thing that makes us freak out. Common phobias include fear of height, flying, water, spiders, being alone, or being in public.

20. What are you mostly obsessed with?

This is not necessarily a hobby, but something they find irresistibly spellbinding.

21. What’s your favorite movie?

It’s great to know if the person loves movies, especially if you’re also a movie lover.

22. What’s your favorite music?

The answer will clue you in on the type of music they love. You might also get to know whether they’re into dancing or not.

23. What’s your favorite food?

It’s important to ask this question as early as possible in a conversation. The last thing you want is to order a hamburger for a complete vegan.

24. What’s your worst day of the week?

Most people hate Mondays for obvious reasons. However, this may not always be the case for some people. The secret to this question is to know why they hate that day and what you can do to brighten it up for them.

25. What’s your favorite social media platform?

Not only are you interested in finding out whether they’re a Facebook, Twitter, YouTube, or Instagram person. You also want to know how much time they commit to social media.

26. How do you get rid of stress?

An excellent question to know how they detox their minds.

27. Where do you see yourself in 5/10/20 years?

Everybody dreams of a better future, so find out what their future ambitions are.

28. What’s your role model?

We all have that person we deeply admire for their personality and accomplishments.

29. What’s the one thing you can’t live without?

Common knowledge dictates that humans can’t live without oxygen, water, or food. But expect a more exciting and surprising answer to this question.

30. Why did you ask me out on a date? /Why did you accept to go out on a date with me?

This is an ideal question to ask a potential love interest. It helps you gauge their level of interest in you.

Wrap Up

Starting a conversation is not a walk in the park. But it’s also not as difficult as most people imagine. For the most part, it comes down to assuming the right posture and asking the right questions. When choosing the right conversation starter questions, insist on those that are open-ended, interesting, and insightful.

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