Going Deeper: Conversational Kick-Starters & Connectivities

Deep connections are the secret to a happy, healthy life, and great friendships are built on a foundation of embracing vulnerability. If it gets awkward, you’re doing something right!

by | Aug 27, 2019 | article

Studies all around show it’s just as hard, if not harder, to connect with people past those surface-level early meetups we’re all so accustomed to. Whether you’d just like to talk about something other than how things are going at work or you’re determined to take a few friendships to the next level, it takes a little skill to navigate the waters of deep relationships. Use these conversation starters and connectivities to cultivate satisfying conversations, learn more about your people, and feel more deeply connected, more often.

Conversation Kick-Starters

The quickest way to deepen your relationships is to have real conversations. Sure it’s great to catch up about the basics, but you’ve gotta learn to ask real questions, listen, and give real answers if you want what’s on the other side of that superficial barrier. Steer conversations away from small talk with questions geared toward better understanding what makes people tick.

Start with a Light, Conversational Appetizer

Truth is, not everyone will be ready to go deep when you are. Test the waters first by going slightly beyond “what’s new with you?” — people often feel boxed into customary responses. Ask these more open-ended options instead:

  • What’s the best thing that happened to you lately?
  • What’s something you’re grateful for this week?
  • What’s on your mind?
  • What are you working on in life right now?
  • What’s it like being you these days?

If They’re Game, Dig in a Little

Understanding the motivations behind your friends’ personalities, goals, and dreams makes you a better companion by proxy — you know why they do what they do and say what they’re saying. You’ll also learn why they appreciate having you around. Instead of an echo chamber of individuals spattering off facts about their lives, your conversations begin to hum with reciprocity, leading both of you to seek more of (and from) them.

  • If people really knew you, what would they know?
  • What do you aspire to do by the end of the year?
  • Where’s the magic in your life?
  • If you were going to give a TED Talk, what would it be about?
  • What would you like to hear, say, or talk about more often?

Order Dessert! Depth Is the Icing on the Cake

After you’ve known someone for a long time, you start to see the world through their eyes. You offer each other perspective and support through a variety of life experiences, bringing you closer while teaching you there’s always more to learn about each other. Try one of these questions to tap into what really makes the other person tick.

  • What is the closest you’ve been to death?
  • How do you deal with disappointment?
  • What would you say was the defining moment in your life so far?
  • What stories are you telling yourself about where you are in life right now?
  • What conversations are you having with future you?
Listen on Wellness 3.0: Communication | Chad Littlefield

Podcast: Start with Intention for Conversations That Matter

Listen to this interview with Chad Littlefield, a man on a mission to create conversations that matter, to learn what it takes to strike up a conversation with somebody on a bus or a plane. More importantly, learn how not to feel uncomfortable afterward. His advice: Start with intention to create connection and ask powerful questions.

Connectivity (Connection + Activity) Ideas

Connectivities are fun and engaging mini-games and questions designed to kick start small talk and leave you feeling more connected to the people around you. Try some of these ideas to dig deeper into your relationships.

The “Yes and…” Game

For this game, one person starts with a short statement like “Today I went to the store.” The second person then responds with “Yes and…” before adding to the story with the next line. This can continue back and forth for as long as you like. By listening to each other and building off what the other person says you create a fun story and feel more connected to each other.

Eye Gazing

This next activity sounds deceptively simple. Sit with your partner and look into each other’s eyes for one full minute. You will be amazed at how much more connected you feel at the end of that minute. Simple, but effective.

Compliment Battle 

Who doesn’t love to receive a compliment? For this activity, take turns complimenting each other. Whoever comes up with the most genuine compliment is the “winner,” but really everyone wins. 

Tell Your Story

Take two minutes each to tell your life stories. Then start over and tell it in a way you never normally would. This is a great way to learn about your friend and yourself. What parts of your life do you usually highlight? Do they sound like an entirely different person when they focus on different facets?

You’ve tapped into the secret of a happy, healthy life (huzzah deep connections), now get out there and start practicing. If it gets awkward, you’re doing something right! The best friendships are built on a foundation of embracing vulnerability and living perfectly imperfect lives together. Let yourself bask in the glow of growing friendships, and just have fun with it.

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