The Best Deep Conversation Starters to Impress Anyone, Anytime!

Have some deep conversation starters in your chatting armory and impress everyone with your communication skills! You’ve got this.

We’ve all been there. Wracking your brain for deep conversation starters, so your convo doesn’t fall flat.

You meet someone for the first time, or perhaps you’re on a date, and you really can’t think of anything to say. Your mind goes blank. The silence seems to go on forever. You’re willing them to come up with something scintillating to talk about, but they seem to be just as out of ideas as you.

Awkward, right?

I’ve been in this situation more times than I can count. I decided that enough was enough. No more awkward silences, no more wishing someone would walk in and save the situation. What did I do? I came up with a list of deep conversation starters which I could fall back on at any time and boom! Instant deep and meaningful conversation to impress anyone.

[Read: Funny conversation starters – 40 lines to instantly fit right in]

Deep conversation starters to memorize for future chats

Of course, the type of question you ask depends on the person you’re speaking to. If it’s your boss, it’s probably not the best idea to ask them to tell you about their most embarrassing moment; instead, ask them about their goals or something professional. However, if it’s a crush, you can afford to be a little cheeky. Perhaps ask them one of the more searching questions on the list.

Because I’m feeling generous, I’m going to share my list of deep conversation starters with you, so you no longer have to endure another awkward silence again.

You’re welcome!

#1 What are your main goals in life? This is a great go-to for chats with someone in authority, such as a manager or someone you’re really trying to impress on a professional level. You can angle it to show that you want to learn from them, so ask them about their goals professionally and see what advice you can get from it.

You never know, you might find something useful in there that you can emulate. If not, at least the conversation doesn’t run into an iceberg and sink. [Read: How to balance your career, social life, and dating life]

#2 If you died today, what regrets would you have about your life? It might sound depressing to consider death, but it’s definitely one the deep conversation starters that will get a chat going and could easily lead to other questions. Think about your input into the conversation here too – what would your regret be?

Remember that conversations need to be two-way, so it’s a good idea to add your own regrets in and perhaps compare. You’ll certainly get to know the person pretty well over the time it takes to have the chat too. [Read: How to not give a fuck: Your guide to give less fucks and enjoy your life]

#3 If you won the lottery, what is the first thing you would buy? This question can tell you a lot about a person! If they go straight into the long list of material goods they would buy, perhaps that says they’re literally a materialistic person.

However, if they tell you that they would buy their parents a house or a car, or help out someone in their family, that tells you they’re a pretty selfless kind of person. It’s also useful to think about what you would buy, it gives you food for thought! [Read: 20 revealing questions to get to know someone better]

#4 Who is your hero and why? The great thing about this type of question is that it isn’t closed, so there’s no way to just give a one word answer and leave it at that. If they do just say a name and say it’s because they’re cool, then they probably don’t actually want to have a conversation with you!

There’s plenty of scope here for expanding on the answer, so it’s one of the best deep conversation starters you can keep in mind. It also tells you a lot about them once more! [Read: 20 funny get to know you questions to bond with anyone instantly]

#5 What is your biggest fear? They might not actually tell you their true biggest fear, because it’s a little personal and they don’t know you so well, but they can easily come up with something interesting to tell you. It gets the conversation going. Again, add in your own fears and open up a little, expanding the conversation further.

#6 If you could go back to your childhood, what advice would you give your younger self? Ah, this is an interesting one! This is one of those deep conversation starters that gives you a glimpse into the inner psyche of the person you’re speaking to.

It helps you to understand them a little better. It’s also a very good question to ask if you want to keep the conversation going for a little longer, i.e. you have some time to kill! You can add in your ideas, they can comment on them too, etc. It’s a great way to get to know someone. [Read: How to keep a conversation going with the opposite sex]

#7 If you could live anywhere in the world, where would you live? This is a fun one to think about. It’s likely they’ll say somewhere hot and sunny. But if they give you a one word answer, the instant follow up question for you to ask is “why?”

Deep conversation starters such as this are great for trying to get a particularly shy or quiet person to open up a little. And it uses the imagination which means plenty of scope for a longer chat. [Read: 15 conversation starters for the shy and socially awkward]

#8 Describe your perfect day. Again, this is another one which uses deep imagination. Get things started by describing your own perfect day and then encourage them to do the same. Again, all of these deep conversation starters really help you to get to know the person you’re talking to pretty quickly in a way that regular conversation subjects just don’t do. You can also prompt the conversation by asking why they’d do a certain thing and what it would mean to them, etc.

#9 Which celebrity did you love when you were younger? This is a fun one to ask. Most of us have a cringe-worthy celebrity crush to look back on! This is great for asking someone who you want have a lighthearted conversation with, but it also helps you delve a little deeper too, which allows you to get to know them.

The great thing about these deep conversation starters is that they all use imagination and memories. Really, it’s the best way to understand someone at their very core. [Read: How to get to know people, open up and make new friends]

#10 What do you think about …. *news story of the moment*. There is bound to be some topical subject going on when you’re attempting a conversation with someone, there always is.

In that case, just ask them what they think about the latest big news story. It will help you to break into a deeper conversation as a result. Most people have an opinion they’re happy to share, so just ask! [Read: How to get to know yourself and reveal your life’s true passions]

#11 What items are on your bucket list? A little earlier we asked about goals, but this is slightly different. These are the things they would like to do, not the things they’re aiming towards. This one also uses a little imagination. You might hear some rather creative items, such as bungee jumping or maybe skydiving! Perhaps you didn’t know that person had such an adrenaline junkie side to them! [Read: How to be fearless: Set aside fear and live your life]

#12 What is your most cherished memory? Asking about memories is a real conversation starter. It’s a great way to get someone to open up. They’ll probably get a fond look on their face and tell you about something from their childhood, or a date they went on with their partner. It’s a great way to get a real conversation going.

[Read: Drawing a blank? Try these 25 good conversation starters]

These deep conversation starters are easy to memorize. They can be stored in your memory bank for times when you want to get a conversation off the ground!