Deep Conversation Starters to Intensify Your Connection

Published March 3, 2021
Deep conversation starters

As online dating becomes more and more commonplace, many people are feeling the pressure to choose between witty one-liners or deep conversation starters to connect quickly with their potential partners. However, you needn't worry about having the tendency to turn into a wallflower when you can definitely stand out from the crowd using these different deep conversation starters.

Getting Into the Thick of It

First and foremost, an important thing to remember when trying to get to know someone is to be an avid listener. According to one neuroscience study, "active listening can stimulate the brain's reward system." In being an attentive listener, you've oiled the gears of whatever topic you and your partner will discuss next so that when that time comes neither of you will feel forced to keep the back-and-forth going.

Getting into the thick of it

Deep Conversation Starters

When you want to start getting into the heavier stuff with a partner, you'll want to feel out what sort of topics they're most drawn too. Passionate people can talk for hours about what they love and enjoy, and this can set the mood for building layers of shared experiences and for unveiling hidden secrets. So, here are a few different kinds of deep conversation starters to help you enrich you and your partner's relationship.


These conversation starters are perfect to get to the heart of all the thrill seekers out there who have a growing National Park sticker collection and pages and pages of stamps in their passports.

  • Where in the world would you most like to see the sunrise from, and why?
  • What's the most dangerous stunt you've ever pulled and come away unscathed from?
  • If we had two-weeks for an unlimited road trip, what would our roadmap look like?
  • Is there anywhere you've visited that you've been disappointed in, and why?
  • What is your favorite way to travel (planes, road trips, cruises, and so on)?
Deep cnversation starters

Feeling Nostalgic

From Blockbuster rentals to 90's Nickelodeon game shows, everybody loves to remember the best moments from their childhood. According to the Institute for Family Studies, nostalgia makes people feel connected and feel "motivated to connect." What better way than to share these nuggets of childhood nostalgia than with your partner?

  • What is your favorite childhood memory associated with your five senses (taste, touch, smell, sight, and hearing)?
  • If you could relieve one vacation from your childhood, what would it be and why?
  • What was your favorite summertime activity as a kid?
  • What clothing item or accessory do you most associate with your childhood, and why?
  • What is your most embarrassing memory from when you were a kid?

Pondering the Universe

One intrinsic aspect of forming relationships with people is human's need to feel connected in the overwhelming vastness of the world and the universe beyond. In a time where there are so many questions that have yet to be answered, you can take comfort in the concrete answers that come out of these philosophical inquiries.

  • Do you think our ancestors would actually enjoy the future if they were given the opportunity to see it?
  • Which would you rather explore, the far reaches of space or the depths of the ocean, and why?
  • Do you think plants and animals experience feelings, and why?
  • Which planet in the solar system would you most like to explore, and why?
  • What do you think the end of the universe will actually look like?

For the Dreamers

Everyone has had at least one dream they've wanted to make a reality, and these unique motivations can provide incredible insight into the people around you. Here are some conversation starters that you can use to draw out the most wild and fantastic of people's dreams.

  • If you could live through one historical event and survive, what would it be?
  • Which would you rather have, enough money to travel the world whenever you wanted or have someone pay for your dream house?
  • What was the moment when you've felt the most at peace in your life?
  • What are your go-to comforts for when you're feeling down and need to pep yourself up?
  • What opportunity do you feel like you were most cheated from (a job, a scholarship, and so on)?

Getting Vulnerable and Digging Deeper

One of the most daunting aspects of starting a deep conversation with a potential partner is the expectation for you to reveal the deepest parts of yourself in exchange for learning about your partner's. Yet, Dr. Brené Brown's research on vulnerability proves that "vulnerability is the birthplace of love, belonging, joy, courage, empathy, and creativity." Thus, if you really want to strengthen your relationship, you want to get comfortable with being uncomfortable, and these deep conversation starters can help you expertly navigate that vulnerability.

Deep Conversation Starters to Intensify Your Connection