6 Apps to Boost Your Social and Conversational Skills

Make new connections and strengthen your current relationships with these apps designed to spark engaging conversations. Whether you need to get the discussion going on a Zoom call or liven up your dinner party, great conversation starters are often needed.


From icebreakers to meaningful discussions, these apps give you something to chat about. You might spark a new friendship or learn something new about someone you’ve known forever.


1. Gather – Conversation Starter

Shuffle through the app’s hundreds of conversation starters, ranging from lighthearted would-you-rather-type questions to philosophical discussions. Categories include questions for families, kids, couples, and friends so that you can tailor them.

There’s also a vast selection of conversation starters for specific events, whether you’re celebrating a graduation or chatting with your book club. A section of work-friendly questions can help you understand your colleagues’ talents and obstacles. This section is also an excellent resource for fun icebreaker questions for virtual meetings.

For people you’ve just met, you can ask about their hidden talents or dream jobs. Couples can discuss the story of their first date or favorite outfits. There’s also a section of Never Have I Ever questions for the 18+ crowd that can live up a party or other get-together. (Who will admit to snooping through a partner’s phone?)

You can explore most of the app for free, but a subscription provides access to all the questions.

Download: Gather – Conversation Starter for iOS (Free, subscription available)

2. TableTopics: The App

Based on the popular conversation game, the TableTopics app offers icebreakers for family gatherings, virtual and real-life meetings, dinner parties, and basically any other event. Themes include geeky pop culture, food and cooking, travel stories, and many more topics. Each topic includes a free preview to get a sense of the questions, and you can opt to purchase the full deck for each one.

The What Would You Do section includes questions about topics you might not cover otherwise, such as faking sick to get out of obligations. Meanwhile, the Dinner Party deck gets the conversation going by talking about your favorite cars or beloved teachers from your past.

For younger people, you can ask questions specifically designed for kids or teens. Ask your children what makes them feel better when they’re sick, or find out which five foods your teenager finds repulsive.

You can also answer questions designed around seasonal activities, such as camping or picnics. (What’s your favorite way to cook s’mores, lightly roasted or burned?) There’s also a selection of questions designed specifically for book clubs to spark conversations about your latest read.

Whether you’re chatting with people in real life or making the most of your Twitter DMs, these questions are a fantastic way to kick off new discussions.

Download: TableTopics: The App for iOS | Android (Free, in-app purchases available)

3. Longwalks: A Question Each Day

Recommended by Oprah, the Longwalks app provides a new question every day that you can answer and share with friends online or in person. You can also use an online community to form new connections, making it a great platform for meeting new friends.

Each day, you get a surprise question to answer on your own. There’s also the option to view Hints and see what others in the community have written. Although the questions appear simple, they can encourage you to stop and reflect before answering. Different days can focus on a particular theme; for instance, you reflect on vulnerability on Wednesdays. Questions for the following day don’t appear until midnight, so it’s always a surprise.

Questions might ask about things you want to change in your life, your passions, and reasons for gratitude.

It’s fun to provide your answer and see how community members responded because there can be so many reactions. People open up about their careers, relationships, goals, and aspirations with these short responses to thoughtful questions.

In addition to the daily questions, you can also follow other users, join clubs, and invite your own friends to join as well. The clubs include groups for teachers, book lovers, photographers, and college students, for example.

At this time, the app is completely free to use, so you can jump in and start engaging with the community at no cost.

Download: Longwalks: A Question Every Day for iOS | Android (Free)

4. Never Have I Ever: Party Game

Learn new facts about your friends with this classic game, which offers hundreds of questions you’d never think to ask. For example, you can find which friends have appeared on TV or walked out of a bad movie.

The simple app gives you two responses to each question: Done That or Never. You roll through the questions very quickly. For the most part, it’s a fantastic way to liven up any gathering, just like the best Alexa party games. You’ll have something worth discussing, at any rate.

If you enable the statistics feature, you can see how other app users voted. It’s reassuring to see how many others have also walked into a glass door or sent a text message to the wrong person, for instance.

You can access the Normal and Party questions for free, but the Extreme and Couples packs require a one-time purchase. Also, you will contend with advertisements while using the free version of the app, but you can get through several questions before they pop up.

Download: Never Have I Ever: Party Game for iOS | Android (Free, in-app purchases available)

5. Big Talk

Spark meaningful conversations with this app, which offers interesting, open-ended questions. Different decks focus on areas such as work, travel, and family. Talk about where you would go on an epic summer road trip, things you miss from childhood, and many more fascinating topics.

Art questions encourage you to think about the things that help inspire your creativity, while Party questions include things like whether or not you’d venture to outer space if offered the chance. There’s even a selection of Self questions you can use to reflect on your childhood or think about the people you trust the most.

These thoughtful, open-ended questions are great for inspiring meaningful conversations with anyone you’d like to know better.

Download: BigTalk for iOS | Android (Subscription required, free questions available)

6. What Would You Choose? Rather

Liven your conversations with this app, which takes the classic game and adds hundreds of questions to the mix. Would you rather have ten pets or no pets at all? Have a time machine or a teleporter? Sometimes silly, often imaginative, the questions will give you and your friends plenty to discuss in no time.

These questions will make you consider brand-new scenarios and try to arrive at the best of two decisions. The Normal collection of questions is free to use with advertisements, or you can opt to remove the ads with a one-time purchase. The deck of Adult questions requires a purchase as well.

Download: What Would You Choose? Rather for iOS (Free, in-app purchases available)

Go Beyond Small Talk With Apps That Spark Conversation

Whether you’re mingling with strangers or people you’ve known forever, these apps will help keep your conversations flowing.

Ask questions that inspire deep connections, or liven up a party with silly question games. In any case, you’ll always have something to talk about.

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