If You Want to Be Interesting, Be Interested! Bookmark These 47 Conversation Starters For Any Situation

Needless to say, the last several years completely transformed our social lives. Suddenly, we held conversations with the very same people we previously saw every day at work from miles away. There were no longer casual chats to be had in the office kitchen or when we peeked our heads over our computers. And of course, with the lack of social gatherings, conversations with our friends—much less new acquaintances—became all the more strained. But I truly believe that Covid enabled us to re-prioritize how we want to be spending out time. And our go-to, small talk conversation starters of yore just weren’t going to cut it.

For me, shallow conversations feel even shallower, and my tolerance for negative energy has dwindled. On the flip side, I find myself craving those soul-nourishing conversations that leave me feeling alive and satisfied like never before. They go beyond your favorite restaurants, beyond celebrity gossip, and beyond the minutiae of everyday life. These deeper conversations often take place with family and close friends. But I’ve also discovered that something special happens when I open myself up to connection with a new person, too.

Featured image from Ashleigh Amoroso’s spring happy hour by Michelle Nash.

Image by Belathée Photography

47 Conversation Starters That Will Make You the Most Interesting Person in the Room

That level of true connection requires vulnerability—stepping into and embracing the fear of sharing ourselves truly and authentically. Discovering shared similarities with a stranger, or uncovering a kindred spirit in an acquaintance, holds its own kind of magic. It reminds me that people and relationships can be the most exciting moments in the adventures of our lives.

Discovering shared similarities with a stranger, or uncovering a kindred spirit in an acquaintance, holds its own kind of magic.

So, how can we cultivate more of those types of conversations, whether we’re at a dinner party, a networking event, or lunch with a group of friends? It starts with the intention we bring to the experience. If we go into it searching for true connection and vulnerability, we’ll usually find it. We can approach each interaction with genuine curiosity that makes others feel seen, heard, and valued. In this space, the conversation naturally flows… but I also like to enter into it with a few great conversation starters up my sleeve, too.

Image by Michelle Nash

3 Game-Changing Tips for Impactful Conversations

1. Set an Intention for Connection

There is one thing that separates a conversation that feeds your soul and one that leaves you feeling empty: it’s how much presence each person brings to the experience. Distractions like looking at a phone or having self-conscious thoughts are an automatic barrier to connection. But when both people fully show up? It’s a totally different experience.

I like to use transitions between activities as a time to set my intention for the conversation I’m about to have. Next time you’re about to meet a friend or walk into an event, take a minute to ground yourself before getting out of the car. Breathe deeply and visualize the type of person you want to be in that exchange. By reminding myself to bring curiosity and presence to a conversation beforehand, I can show up as my best self.

Image by Michelle Nash

2. Gather Context About the Other Person

I’m going to tell you about a little conversation hack that I’ve never shared before. First, you should know that I have a terrible memory, which sometimes makes connections with friends I haven’t seen in awhile challenging. (There’s a good chance I’ve forgotten half of what they told me when I saw them months ago!) Here’s what I do.

After getting together with a good friend, or anyone I’d like to cultivate a friendship with, I pull up my Evernote and write down anything they shared that I want to remember and ask them about later. These could be upcoming trips they’re taking, personal or professional challenges, details about their family members, etc. It’s usually just quick bullet points to jog my memory. Then, the next time I have something scheduled with them, I search my Evernote files for their name, and boom: I can enter into that experience with great conversation starters and ideas for things to ask them about.

3. Consider What You Want to Share—and What You Don’t

You know that feeling when you’ve overshared, gossiped, or accidentally talked about yourself the entire time? I call it a social hangover, and it’s the worst. To avoid that feeling as much as possible, I like to brainstorm a handful of things to share about my own life in advance of a conversation, and also consider if there’s anything going on that I don’t want to bring up. This is helpful in a couple of ways:

1. Thinking about what I do and don’t want to share with a particular person challenges me to think about my level of intimacy with them. If it’s someone I want to build intimacy with, I can intentionally be a little more vulnerable. However, if it’s someone I don’t fully trust, or have no desire to become closer with, I can avoid topics that I’ll regret bringing up later. Remember: people earn your trust through their words and nonverbal cues, and you don’t have to be vulnerable with everyone in your orbit.
2. If I’m going to an event with Adam, we can touch base beforehand on anything either of us would prefer not to share with the group. That way, we’re not faced with any of those awkward moments where one partner is obviously uncomfortable while the other relates a “funny story,” and we can respect each others’ boundaries while still being as open and vulnerable as possible.

Okay, now that we’ve laid the groundwork, how do you spice up a conversation? Let’s talk about conversation starters to help you spark deeper connection.

Image by Michelle Nash

Intimate Conversation Starters

Why is it that sometimes, a dinner date with your best friend, your partner, or your mom can leave you feeling more connected, while other times, it leaves you feeling flat? It usually comes down to how much you both showed up with presence, practiced active listening, and asked good questions. Here are some of those questions that can serve as deep conversation starters for couples, close friends, or family members. Though some of them might initially seem simple, I love that they stand as an open-ended question that’s likely to inspire extended, in-depth conversation.

1. What was the highlight of your week?
2. What was the best gift you’ve ever received?
3. When you were a kid, what did you think your life would look like now?
4. What’s your love language? How do you like to be shown love?
5. What’s your favorite memory of us together?
6. What’s something new you’d like to try this year?
7. What was your first job? Did you like it?
8. If you could travel back in time, where would you go?
9. In what ways does your first crush resemble your partner today?
10. What is the last movie you saw that made you cry?
11. What is your dream job? What’s keeping you from pursuing it?
12. What is a secret that no one knows about you?
13. When was the last time you truly experienced flow? What were you doing?
14. Who is your role model?
15. What is your earliest memory?

Dinner Party Conversation Starters

I love to initiate lively, interesting dinner party conversation by brainstorming a few questions ahead of time. This practice has led to some of the most fun memories ever around a table! Once you’ve thought of your questions, you can either throw them out to the group when there’s a lull in conversation, or you can write them down on pieces of paper to hide under guests’ plates. When everyone’s seated and the time feels right, you can randomly ask a guest to pull out their question and pose it to the group.

1. What’s your biggest fear?
2. If you were going to open a restaurant, what would the concept be?
3. What’s the strangest thing you believed as a child?
4. When you were a kid, what did you want to be when you grew up?
5. What is your least favorite chore?
6. If a movie was made of your life, who would play you?
7. What was your biggest fashion faux pas ever?
8. Share your most embarrassing moment.
9. Who is the most famous person you’ve ever met?
10. What’s the most adventurous thing you’ve ever done?
11. If you could take a vacation anywhere in the world, where would you go?
12. What was your favorite birthday? What made it special?
13. What are your favorite things about yourself?
14. If you could have any two superpowers, what would they be?
15. What do you most want to accomplish on your bucket list?
16. What do you think your favorite color says about yourself?
17. What about you garners the most compliments? (Your smile, your sense of humor, your kindness, etc.)
18. Which cartoon character to you most resonate with?

Image by Teal Thomsen

Conversation Starters with Strangers

These questions are great to have in your back pocket for events where you may not know a lot of people (like a wedding or networking event), or even for casual conversations that pop up at a coffee shop or in line at the grocery store. A collection of go-to conversation starters at a party will not only make you a more interesting person—they’ll lead to the types of unexpectedly delightful conversations that are truly the spice of life. And with a good conversation starter up your sleeve, anything is possible.

1. Are you working on anything exciting lately?
2. Have you tried any new restaurants lately?
3. What’s your favorite place you’ve ever visited?
4. So, what’s your story?
5. Tell me about you.
6. Are you a morning person or a night person?
7. If you had to eat one type of cuisine for the rest of your life, what would it be?
8. How do you know the host?
9. For couples: how did you two meet?
10. Have you been to this event before?
11. What’s the best advice you’ve ever heard?
12. Are you having a good time? (aka, a great alternative to the bland, “How are you?”)
13. What is your favorite book?
14. Is there a favorite TV show you’ve loved lately?

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