25 Best Conversation Starters To Leave A Pleasing Impression On Anyone

Written By:

Louisa Davis

Written By:

Louisa Davis

Best Conversation Starters To Leave A Pleasing Impression 2

“The happiest conversation is that of which nothing is distinctly remembered, but a general effect of pleasing impression.” –  Samuel Johnson




Imagine you have just got an opportunity to talk to your crush or a potential customer for the sales pitch and you say something weird or silly or go for extreme political debate that led to a bad first impression. Forget about a memorable conversation, the person would never want to meet you again. The result is – REGRET. Now, this is where conversation starters come in handy.

We have all had an experience of talking to that person who is easygoing, can talk about any topic irrespective of your age, and gender, make you feel comfortable and finally leave you smiling. Now, this is the art of conversation. Such people have a knack for good communication and you will always be interested to talk more and spend time with them. You may also end up falling in love with that cool girl or guy.



You need good communication skills to modify an ordinary topic into something that is interesting, engaging, and enjoyable. Such discussions are memorable and open opportunities to connect with potential partners or business referrals.

art of conversation

But, that happens when you have a goal in your mind. It can be anything dating, selling your new products, sharing experience, extracting new ideas for your upcoming presentation, just have fun, know about new investment ideas, or anything else.

Think about why millions of people watch TEDx Talks. What keeps us hooked on till the end?




Besides good verbal communication skills, you do need strong non-verbal cues such as appealing body language and facial expression. Cracking a funny joke with a serious expression doesn’t make sense. Right? Your smile, tone of speech, eyebrows, and eye contact also add to the dazzling conversation.

If you want to come off as an interesting person instantly, you must master the art of conversation. 

Read on to know the traits of good and bad conversations in any situation and you will never struggle to make new connections or build successful relationships.

Read Science Reveals Why It’s So Hard to Maintain Eye Contact While Having a Conversation

Best conversation starters to leave a pleasing impression on anyone

1) Conversation starters to socialize with strangers –

1. What’s the last new skill you learned?

2. What’s keeping you busy lately?




3. What do you think about this party?

4. What’s something you’re good at that would surprise people?

5. What brings you to this city?

Tips –

  • Be relaxed.
  • Mix work and play.
  • Keep the topics lighter.
  • Don’t dominate the conversation.
  • Encourage reciprocity.

2) Conversation starters for a social event –

1. Why did you choose this venue?

2. Do you have a signature drink?

3. How was your trip to Australia?

4. Being an entrepreneur with a family, how do you attain work-life balance so well? Can you give me some ideas?




5. Are you looking forward to anything in the next few weeks?

Tips –

  • Avoid serious topics.
  • Keep smiling and be yourself.
  • Think of sales opportunities without directly talking about business or job.
  • Ask questions to know more people quickly.
  • Have a good story to tell.

Read 24 Questions To Ask A Guy To Determine Compatibility In A Relationship

3) Conversation starters for conference –

1. If you were running this conference, what would be your presentation topic?

2. Have you heard this speaker before?

3. If you could meet one speaker from this event, who would it be?




4. What was the most interesting part of the conference?

5. Do you think the IT industry needs more conferences like this?

Tips –

  • Ask thought-provoking questions.
  • Ask what they have learned from the event.
  • Know other people’s objectives.
  • Talk about engaging ideas.
  • Maintain a friendly attitude.

4) Conversation starters for dating –

1. What is going great in your life right now?

2. If you got a free ticket to anywhere in the world tomorrow, where would it be?

3. What’s your favorite Netflix//television series?

4. What is something I would have never guess about you?



5. What’s your dream job?

Tips –

  • Talk about happy memories.
  • Avoid close-ended questions.
  • Find out passion and shared interests if any.
  • Dig for a little info.
  • Be curious.

Read 4 Ways To Get Your Man To Open Up And Start Communicating With You

5) Conversation starters for family and friends –

1. What is something that will always make you laugh?

2. If you could be a character from any book, what character would you be? (when talking to kids)

3. Do you have any unfulfilled wish?

4. What is your biggest regret?


5. What is your favorite thing about our relationship?

Tips –

  • Start with fun topics.
  • Ask questions that can engage every family member.
  • When talking to kids listen more and show interest.
  • Evoke deep conversation with friends.
  • Ask questions that can get you closer to your spouse

What makes a good conversation?

1) Non-routine

You talk more than just climate, hobbies, or job. For example, “If you could live anywhere in the world, where would you live?”. These are meaningful questions that will jolt the person you’re talking to out of autopilot.

“Conversation about the weather is the last refuge of the unimaginative.” – Oscar Wilde

2) Engaging

You can start with questions that are timely, relevant, and specific. It will make the other person easier to contribute. But don’t forget to pour in emotions. Taking about the latest happening in the world – technology, business, movies, fun facts from social networking can evoke excitement and prevent small talks.



Read Conversations That Help Connect and Build More Intimacy In Your Relationship

4) Personal 

These questions happen when you want to know the person at a deeper level. But never make the conversation partner uncomfortable or embarrassed. You know what topic suits your friends, family members, and corporates. For example, “Why was your best boss your best boss?”

5) Open-ended

Asking broad questions is the surefire way to keep the conversation going. For instance, “Are there any skills you thought would be crucial to your job that turned out to be unimportant?” is something that cannot be answered in one word. Such conversation starters typically generate interesting discussions.

What makes bad conversation?

1) Boring

Asking the same standard questions that are ages old, doesn’t lift the mood and cannot spark a conversation. People who are less friendly and enthusiastic are highly likely to be boring conversationalists. Asking your girl “what do you do?” can shut her brain but not if you ask “what are you passionate about?”. The second question helps you find out more about her.

2) Awkward

These are conversations that can make even a bold and strong person uncomfortable. They may want to run away and never look back. For example, “How would you plan your ideal funeral?” or “Has anyone told you that you should lose some weight?” Such conversations lead to embarrassment and can end the relationship before it starts.

3) Offensive

When you ask questions that are none of your business or implies a value judgment.  For instance, “Are you a virgin?” or “How much bank balance do you have right now?”. Such rude conversation starters can annoy anyone including loved ones. 

Read The Type Of Communication Which May Be Hurting Your Relationship

4) Impersonal

You know them; these are close-ended questions that just elicit “yes” or “no” answers. “Do you like traveling?”, “Are you enjoying the weather today?” and so on. It is a clear sign that you want to be polite and make no efforts to know the other person at a deeper level or keep the conversation going.

Now you know what makes a bad conversation. So, avoid it all costs.


I hope you got the idea of what makes the bad and good conversation starters. The list of interesting conversation starters helps you spot that small opening (when meeting new people) in any situation and advance inch by inch so that you earn a chance for a second conversation.

Do you know of any other bad or pleasing convo starters? Leave a comment below.

The Art of Conversation 25 Great Conversation Starters
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— About the Author —

Louisa Davis

Hi there! I’m just a normal person enjoying the process of life. Practicing Buddhism, I believe in the law of cause and effect. Reading and writing is always a pleasure. I enjoy researching on a range of subjects – science, psychology, and technology. Nothing can satiate my soul than good music, horror movies, psycho-thriller, and crime stuff. I enjoy photography, music and watching comedy videos. Talking to people, learning new experiences, sharing my knowledge through blogs, motivating others are things that I always look forward to.
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