How to Have Interesting Conversations


Sometimes when I'm around a bunch of ladies I have a hard time adding to the conversation. Sometimes it's the conversation that's boring. I don't feel like talking about kids. Or the weather. But, most of the time I feel boring. I always think that one of these days I'm going to do something spectacular that everyone is going to want tot hear about. But, when I'm around friends, my life seems so boring and uninteresting.

I know it's self doubt coming in, and so I decided to combat it with interesting conversation questions. Because talking to people is how we connect, and we all crave connection. We want people to know who we are and we want them to like us for who we are. The hardest part can be getting the conversation started. Once it's going, all you have to do is ask interesting questions, and the conversation will naturally keep rolling. Today I'm sharing fun questions to keep the conversation interesting.


The first few listed are what I think are the most common boring conversations. The kids, the weather, weekend plans, and how are you. I'm sure you are way more interesting than I am, but these conversations always leave me wanting to change the subject. Now I can just ask more interesting questions!

1| the kid talk

When the talk is about kids and you don't feel like talking about kids because they drove you crazy all week, ask an interesting question. Ask if their kids have ever won anything crazy.

My daughter won a boom box. I think she was in first grade. That was crazy. It was so big I had to go to school to pick it up. I don't know why I didn't just tell them to give it to someone else. I think I was in a bit of shock myself! We ended up selling it on Craigslist.

2| the weather talk

When the talk is about the weather ask what their favorite season is and what makes it a favorite. Is it because of some activity they do?

I'm not even sure if I have a favorite season. I just love the change of the seasons and how it makes me change too. Sometimes I get to feeling like I need to really clean out and other times I'm deep into work. I love how nature keeps evolving. It makes me think of that quote, the only thing that stays the same is that everything changes. See? We're not even talking about weather anymore.

3| the weekend talk

When they ask about your weekend plans or about what you did all week and you feel really boring, reply with something interesting. If you did have weekend plans, what would you be doing? If you did rock your week, what would you have done?

I have no idea what I did this week, but the time certainly kept going by. I wish I would have painted the laundry room window so that the first thing I would see when I walk in the door would be a pretty white window sill with a potted plant instead of the bright orange.

4| how are you talk

Don't say fine. Everyone says fine. How are you? Fine. You? Boring. How are you really? People ask how you are to start a conversation. People say 'fine' because they think the person asking doesn't really care how they are and they're just starting a conversation. Nobody want's to go too deep or to open a can of worms in casual conversation. But you know what? You can answer how you really are and still have an interesting conversation.

Think about how you want to be. Think about what went well so far in your day. Tell them how you couldn't wait to get out of bed because you bought some new coffee and you were dying to try it out. Tell them how good your coffee was and ask if they are into coffee and how they like it. I love it when there are hints of citrus and it has a clean finish, but sometimes when it's really earthy it's so good. Especially this time of year, with pumpkin pie.

Think about what's really going on in your life. Maybe like me, you are so ready for a break. I'm working on a project and I wish that I could give it 100% of my time, but as a wife + a mother, it's just not possible. So, how am I? I'm ready for a break and when I finally get one I'm going to buy myself some new perfume and then I'm going to find a cool coffee shop and I'm going to order a latte with extra foam and I'm going to sit and sip on it while I write in my journal. I'm going to observe the people around me because I love people watching. I'm going to sit there and love my break and when I'm done I will probably buy another coffee for the drive home.

5| the wishful talk

Okay, so wishful talk is a bit vague, I know. But talking about our dreams helps make them a reality. The thing is, it's hard to start talking about your dreams in random conversation. Start by asking them what their dreams are, and you will learn so much about who they are.

Ask, if you had to work, what would your dream job be? Or, if you were going to start a business, what would you do? What language do you wish you were fluent in?

I always wished I could speak French. I took it in High School but I'm ashamed to say that I didn't apply myself. Looking back I can see how the teacher was bullied and we students didn't really have to do anything to pass the class. I want to know how to speak French because I'm a romantic at heart. One of my favorite compliments that I ever received was someone telling me that I am a Paris girl. I was like, YES! Someday I'm going there. But first, I need to learn the language.

6| the book talk

Most people think reading is fun, so books are an easy topic. Instead of asking what they are currently reading, ask what their favorite book is. And then dig deeper. Who was their favorite character and what made that character stand out so much? Or, instead of going into one particular book, talk about books in general. What book had the biggest plot twist that you never saw coming? Do you ever cheat and flip to the end when you're still in the middle of the book? Do you ever not finish a book?

It took me 30 years of reading before I decided that I didn't have to finish a book and it still really bothers me to not finish a book. But the thing is, it's so easy to self publish these days, so there are a lot of shoddy authors out there. I don't know if I have a favorite book. Teacher Man by Frank McCourt is way up there. I love that book. Ahab's Wife by Sena Jetter Nasland, but it's so depressing. A Jane Austen Education: How Six Novels Taught Me About Love, Friendship, and the Things That Really Matter by William Deresiewicz because, JANE AUSTEN. Yes, I did write that in all caps. You know, I just love books. I should write a post on books. It would be really long.

7| the food talk

Food. Everyone loves food. I love grass-fed food. But I hate the term 'grass-fed'. It makes me think of cutting my steak open and stuffing it with grass. I put grass-fed butter in my coffee, but I can assure you I don't put grass + butter in the blender with my coffee. Food talk can get so interesting. Especially if you are GF + CF + SF. Food is good. Food is bad. But we all have to eat. What do you love to cook, but not necessarily enjoy eating? Have you ever met someone who enjoyed cooking more than they enjoy eating? Didn't think so. Do you limit your coffee intake? (Never.) What's your guilty pleasure? (Right now, for me, it's Ghirardelli 86% cacao. I know. So good!) And here's an interesting one. Who would you have at your phantom dinner and why them? What is the weirdest thing you have ever eaten?

I never eat anything weird. I don't know why anyone would. Once, when my husband and I went out to eat at a Chinese Buffet I told him that if he ate the squid then I would too. So, of course, he did. And it didn't look good. I thought it was going to come back up. So, of course, I didn't. Can you blame me?!

8| The fun talk

People do funny things. (read: not me) But they tend to forget about them so you have to keep reminding them what was so funny. What is the craziest thing that ever happened to you? Or that you've done? What made you laugh out loud this week? Or, when was the last time you really busted a gut laughing? If you were an animal, what would you be and why?

When it comes to animals, you might think that I would be a buffalo, but what I would love to be is a wild stallion. I can imagine what it would feel like to run with the wind and to stand tall at the edge of cliffs and on mountain tops. The sun beating on my coat, my mane blowing in the breeze, hot air out my nostrils. Looking out over the beautiful land and then running, wild + free. As a kid I always thought horses were so cool, but I was always somewhat scared of them, too. I think they are beautiful. Majestic. Mysterious. Magical.

But as far as having something crazy happening, you have to talk to my husband. Ask him about the animal that was trapped in our chimney. That was crazy. See? I'm telling you, all the cool stuff happens to him. Thank goodness I have his stories!

9| the special talk

Special talk is the things that really show your personality. Where's the best place you've ever visited and what was so great about it? That could be either a vacation or visiting a friends house. What makes you feel taken care of? It's important to share these things. The more we know and understand each other, the easier it is to have conversations. It also helps when it comes time to buy gifts. What is your favorite holiday memory? When you're old, what stories do you want to tell your grandchildren about your life?

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There is nothing better than sitting around with family and friends and talking and talking and talking until you can hardly stay awake. Have those kinds of conversations.

10| this or that

There is one other thing that really makes conversations fun. It's this or that, or, would you rather. Ask someone if they would rather do this or that. And then dig into the conversation and see why they choose that. Silver or gold? Gold because it's traditional. Morning or night? Morning. Always morning. My brain doesn't function at night and I love how quiet it is in the morning and how alive the birds are. I love the suddenness of the sun as she crawls her way into the sky, beaming as she goes. Digital or analog? Analog because it's so pretty. And traditional. And maybe because I like history.

This or that and would you rather are fun to play with kids too. My kids were just doing would you rather in the car the other day. It's so neat to hear what they come up with. Would you rather eat the same foods all the time or would you rather always have to try something new? Would you rather be Godzilla or Trex? It's funny to hear their answers too!

Having interesting conversations makes us feel like we belong. When we feel like we belong we are more open to visiting more. As a bonus, we receive inspiration which helps us get through the week, and can even help us creatively. Seriously. I can't really explain it, but I have felt that. When the weekend rolls around and I set the intention to have interesting conversations, my entire week is so much better.

So, tell me about you. In the comments answer three things about you, and what it is about them that you like:

Silver or gold, morning or night, and digital or analog.