Questions serve a bigger purpose than just being a way to get an answer from someone. 

They help steer conversations, they make us think, and they open up parts of people’s personalities we didn’t know were there. 

This list of 150+ questions to ask friends is split into four categories, each for different situations with friends! 

Have you ever known someone for many years and they say something that makes you think “How did I never know that?”

Asking questions can do so much for a friendship, and asking questions to friends also helps you build social confidence so you can bring your question-asking skills to other settings where you might not be as comfortable. 

From finding common interests to learning how you can best support your friends, questions can be the framework for deep and meaningful conversations friendships. 

Here’s the list of 150+ interesting questions to ask friends!

Have you ever watched someone give a presentation or run a tough meeting at work and thought… 

“How can I be the one doing that?!”

Time for some real talk...

As much as corporate culture claims to reward loyalty and hard work, more often than not, it’s the people who have excellent communication skills who get hired and promoted. 

It’s not a conspiracy, it’s just human nature. 

Learning how to improve communication skills will pay off for the rest of your career.

People who are able to communicate with confidence and finesse have an easier time building a rapport with others. 

When you’re more likeable, people’s cognitive biases tend to assign you other positive qualities as well--whether or not you fully deserve them. 

Unfair? Maybe.

Reality? Definitely.

If you feel like you’re struggling to communicate in your career, or that you’ve been passed over one too many times for that project or promotion, consider learning how to improve your communication skills!

At a certain point in your career, you look around and realize EVERYONE is technically proficient. Developing better communication skills is what will help you stand out from the crowd.

Also, a side benefit is: You'll communicate better in your personal life as well as your career!

​Win/win! Let's dive in!

Let’s dig in!

Do you have a friend or coworker who just seems to know how to build rapport with pretty much anyone in any social situation? 

It may seem like magic..they walk over, start talking, and it looks like they’ve known each other for years--even though they just met!

That’s the power learning how to build rapport.

​And the great thing is...building rapport is a learnable skill... and that’s what we’re talking about today.

There is nothing wrong with being nice. 

Doing things for people who need help, being considerate, being generous--these are all traits to be admired. 

However, there is a very fine line between being “nice” and being a people pleaser. 

So how can you tell the difference?

For starters, being a do-gooder comes with feelings of joy and satisfaction--like when you volunteer at a soup kitchen or help an elderly woman carry her groceries to the car. 

Chronic people pleasing can look similar on the outside (helping a coworker catch up on a project for instance) but comes with feelings of resentment and overwhelm--usually followed by guilt for feeling that way. 

These negative feelings are caused by burnout. People pleasers tend to overcommit to others and say yes at their own expense. 

For many of us (yes, I’m a recovering people pleaser as well!), this burnout and resentment become a vicious cycle that can harm our relationships and reduce our quality of life. 

In this article, we’re going to discuss how to identify people pleasing tendencies and how to stop them. 

You can still be a good person, but you won’t get stuck doing stuff you don’t want to do because you’re afraid of what other people will think of you. 

No more...

• Blowing up your Friday by picking your friend from the airport in rush hour traffic.
• Helping your coworker's sister (that you've never met) move.
• Babysitting your friend’s “I swear he’s really nice” dog. 

Once you stop people pleasing, you’ll be amazed by the sense of relief and clarity. Your relationships will improve, you'll make more genuine friendships and your self-esteem will grow as you learn to stand up for yourself in a way that is confident, tactful, and kind. 

When you stop people pleasing, you know that you're doing whatever you want because YOU want to, not so that others will approve of you. 

Real talk…

EVERYONE feels socially inept at some point in their lives.

It’s just part of being human.

​Maybe you’ve felt socially inept when…

• You told a joke that totally bombed at that backyard BBQ.
• You accidentally blurted out something rude and didn’t realize it until later.
• Your brain seems to shut off and you have no idea what to say in conversations.

If you’ve ever felt like that...I’m here to tell you that it’s okay. It happens!

And the great thing is that being socially inept is something that can be improved. Working on your communication skills can help you become more socially skilled and that feeling of being socially inept will fade away.

Look, we’ve ALL been there… We meet a new friend, or hit up an old friend, and they lay this on you…

“What should we do?”

“Uhh…I don’t know, I’m good with whatever…”

I think it’s always better to have a plan rather than just doing the same old thing.

If you’re looking for things to do with friends, you are in the right place. I have 225+ things on this list that you can do with friends.

So if you’re…

• Looking for things to do with friends on the weekend. Check.
• Looking for things to do with friends at home. Check.
• Looking for things to do with friends when bored. Check.

…I’ve got you covered!

Doing memorable or even challenging things with friends is important because it can lead to peak experiences that you’ll remember for the rest of your life.

Keep this list handy and you’ll never run out of things to do.

If you’re looking for topics to bring up while you’re doing things with friends, be sure to check out my list of 300+ conversation topics and starters.

Ready? Let’s dive in!

Learning how to make friends as an adult is HARD! 

I feel like they should have warned us.

But when you think about it, it makes sense... 

​In school, you have classes, labs, study groups, organized functions, clubs...all sorts of ways to meet new people and connect. 

But once you’re working 8-5 (or 7-6 if you’re like most of us), it becomes a lot more difficult to find the time and energy to invest in other people.

Not to mention finding people your age and with similar interests in the first place!

And once you DO find those people, how do you turn them into friends?
​

• Who sends the first text?
• Is it awkward to ask them to hang out?
• What if it turns out you have nothing in common and you could have been at home with your plants and your dog??

We’ll cover all these questions and more! 

We all know and love (and want to be) those people…

The funny ones.

The ones who seem to crack up co-workers and friends with a word or a well-timed gesture. 

People gravitate towards them--even you. Funny people make you laugh and smile and feel good, who wouldn’t want to be around them?

Even though it can feel like some people are born to be funny and others are born to laugh, you can actually learn how to be funny. 

Learning how to be funny in conversation is a crucial people skill. It will help you: 

• Become more likable.
• Make people more comfortable in your presence. 
• Boost your self-esteem. 
• Improve your mood. 
• Give you the confidence you need to succeed socially! 

Just like any skill, learning how to be funny takes practice! If being funny doesn’t come naturally to you, just remember:

There’s no such thing as a funny baby. 

No one is actually born funny. 

It’s a skill that these people have been working on and building for a long time - probably since childhood. 

The class clowns, the crack-ups we remember those kids. Now that they’re all grown up, they’ve used that experience to their advantage. 

They’ve had a lot more time to learn from trial and error what’s funny and what’s not (and that’s an equally important skill--learning what types of humor to avoid). 

So let’s get to it...

Look, we’ve all been there...

You see someone...and you wonder how to start a conversation with them. 

Then you feel it…

Your mind starts to race - maybe so fast that it starts to go blank. 

“What should I say?” “No, that’s stupid, no one says that!“

And by the time you psyche yourself up to start the conversation, the other person has ordered their tall Americano and sailed out the door.

Ah, such is life, you tell yourself. But it doesn’t have to be this way! 

With the right gameplan, you could be chatting up tall Americano right now and making a new friend.

I know...easier said than done.

​Learning how to start a conversation and developing a gameplan to help you practice and grow your newfound skills takes effort, know-how, and guidance. 

Luckily, you’re in the right place.

When my clients ask me how to start a conversation, my first response is this:

While what you say first IS important, it’s not as important as what you say second.

In fact, for most of my clients, the best conversation starter is: “Hi, I’m [Your Name].”

I know, I know...

It feels almost too simple. But it’s often how we follow up that first statement that makes or breaks the interaction.

Look, sometimes we just need a little extra push to come up with something to say...some extra conversation starters to help that awkward silence melt away.

I got you.

Here are 300+ conversation starters and topics for you use in several different social settings. Use them with friends, coworkers, on dates, or out at happy hour!

(Also: If you need help with how to start conversations, check out this article.)

Pro tip #1:
Find 5 of your favorites and write them down on the notes app on your phone. Use them in your conversations this week.

Pro tip #2:
Be sure to balance asking questions with telling stories, and making statements. (No one wants to feel interrogated!)

​Let's swan dive in... (For fun, I've answered a few of these in bold parentheses)

Look, we’ve ALL been there…

You’re at a dinner party or on a Zoom call with a friend and your mind just goes...blank. 

Maybe the vibe is just off, or the conversation seems to have run its course, running out of things to talk about on Facetime, Zoom, or IRL, can make you feel awkward, boring, and lame.

If you’ve ever felt the growing horror of dead air between you and your conversation partner, don’t worry - you’re in the right place. 

We’re going to help you build up an arsenal of topics and questions that will help you defeat the conversation killing silence!

We can call them conversation starters, but you’ll notice that almost all of them are questions. 

That’s because to keep a conversation going, you have to get people talking! And the fastest way to do that is to invite them to talk about themselves. 

If you’ve read any of my other articles, you’ve likely heard me say this before: 

People love to talk about themselves. 

So let them! 

It may feel like you’re putting the work on them, but I promise they are just as eager to avoid the awkward silences as you are. 

Learning and using the “things to talk about” below will help you keep the conversation flowing and put your conversation partners at ease. 

Let’s dive in!

If you're reading this article, it's a pretty easy guess that at some point or another you've felt...well, boring.

Don't worry! It happens to the best of us!

• You might have trouble speaking up on Zoom calls.
• You might feel comfortable with facts than anecdotes
• You might feel like you can't  match up the rich inner life you lead with the words that come out of your mouth. 

You want to be more interesting and engaging, but you just don't know how to not be boring on the phone. 

Pro Tip: Smile. People can literally hear the smile in your voice even if they can't see you.

You want to enthrall the office with stories about your weekend but you are still Googling "how to not be boring on facetime" instead of doing it. 

The good news is, you are in the right place. 

We are going to cover how to not be boring from top to bottom. These are not vague tips, but real steps you can take with action steps and homework. 

As a social skills coach, I believe in a progressive step-by-step approach to self-improvement. 

Start small, build confidence, repeat. 

I believe that everyone has the ability to improve their social skills and become more outgoing - you just have to tap into that outgoing part of yourself. 

But as any introvert who’s tried to teach themselves how to be more outgoing can tell you - it’s not as easy as it sounds. 

“Know thyself.” -Socrates

Socrates wasn’t playing around when he dropped this philosophical morsel on us. 

He believed that the answer to all happiness and philosophical unrest was to look within where all knowledge already lives, waiting to be remembered. 

I love this idea because it’s an equalizer.

We might have different starting points, but we can ALL improve and grow.

If you want to learn how to be more outgoing--you just need the mindsets and tactics to get there!

​So let’s talk about how to be more outgoing as an introvert, step-by-step. 

Ready? Let’s dive in!

Many of my readers ask me about how to make conversation. 

A conversation that feels natural and smooth.

Good news: These are learnable skills.

Having great conversation skills that you can "turn on" at a moments notice matter when you're:

• Applying for a new job and you're making small talk with the interviewer.
• You log on to the Zoom meeting early and your company's CEO is the only other person in the meeting room?
• You're on a first date where you know you want to make a great first impression.

The better you are with these soft interactions, the better your career, business and social life's trajectory will be.

And the best part?

These skills compound over time.

​Like investing in a 401K, the more connections you make, the easier it is to call up good friends, find jobs fast, and get introduced to more people who can change your life.

Here are 5 tips that you can use starting today to make better, more memorable conversations. 

Every one of these skills are effective individually, but when you stack them together, they become extremely powerful.

When I became self-employed, it was a huge shift.

Gone were coworkers, office small talk, and happy hours.

Instead, it was just me.

And the cat.

At first, it was nice.

"Finally, I can just put my head down and do the work!" I thought.

But, after a couple of months, I realized "Holy crap! I might accidentally become a hermit if I'm not careful."

When you're trying to learn (or in my case re-learn) how to become more social, it's effective to have a few tips to help you get on the right track.

These tips will help whether you're

• A soloprenuer
• A remote worker.
• Or you just need a social shot-in-the-arm to be more social.

Here's a sample of crappy advice you WON'T find in this article:

• "Just be yourself!" (This means nothing. You're always you.)
• "You should read How To Win Friends and Influence people!" (Good book. I'm just sick of hearing people recommend it like it's some kind of magic elixir.)
• "Make sure your handshake is firm and always on top. Show dominance." (WTF?!)

You ready?

Strap in.

​Here are 8 ways to become more social starting TODAY.