Bonding with someone can be difficult. Whether you’ve known them for years or a few hours, cracking someone’s shell isn't necessarily easy.

This is partly because everyone has their own unique needs, says Rachel Moheban Wachtel, LCSW, a licensed therapist who specializes in couples and marriage counseling. When it comes to getting someone to open up, picking up on their specific interests and needs is crucial.

People bond in different ways over different things—perhaps a connection is formed over similar music taste or an obvious commonality, such as a shared workplace or hometown. Even a moment of humiliation, like spilling red wine on the person next to you, can help two people strike a kinship.

When it comes to forming a connection, it pays off to stray away from the traditional ice breakers and ask the unexpected. In other words, get deep to get close.

“The role of the deep conversation is to get beyond the superficial,” says Dr. Megan Fleming, PhD, a clinical psychologist and sex therapist. Sharing from the place of vulnerability is how to truly get to know someone, she adds. The process of connecting is all about someone's willingness to be truly seen, which comes from sharing our most embarrassing, challenging, and often most difficult moments.

Even getting closer to someone you already feel attached to, like your best friend or long-term partner, can get tricky. As Wachtel describes it, people often talk in circles, having the same conversations over and over again. To break out of this cycle and further bond, you have to ask different questions.

To leave behind the surface levels of relationships, two people must show each other vulnerability. “Vulnerability creates more empathy for your partner and that then creates the intimacy and the sense of connection,” says Wachtel.

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So, if you want to get deep, you need to change the conversation and pull out the honest and revealing answers that’ll reintroduce you to the person standing before you. Good news: These experts relayed the secret to bonding with someone. It all starts with asking these 78 hard, non-cliché questions.

These conversation starters are bound to bring you and your bestie or lover to a whole new level of closeness.

When you're just getting started with non-traditional ice breakers:

The big, yet simple, goal here is to get the other person talking. From there, you can tell if this is a person with whom you actually want to be vulnerable.

Fleming recommends having someone talk about their former relationships and their family, paying close attention to their role and accountability. "You can hear in somebody’s narrative about how they talk about their family or previous partners whether or not they can own any of what was their contribution to what didn’t work in that relationship and if that’s something that they’ve thought about and worked on," she says.

These prompts are a great way to suss out personal growth.

  1. How would your closest friends describe you?
  2. If you could have any other job in the world, what would it be and why?
  3. What three words would you use to describe yourself?
  4. What is the best trip you’ve ever taken?
  5. If you could live anywhere, where would you live?
  6. Would you consider yourself funny?
  7. What’s something that always cheers you up?
  8. What movie or TV character do you think you’re most like?
  9. Who was your childhood celebrity crush?
  10. What do you value most in a friend?
  11. How old were you when you had your first crush? Your first kiss?
  12. Are you close to your family?
  13. I’m curious about your previous relationships…

Want to add more ice-breakers to your conversation arsenal? Here's a few fun examples...

preview for Breaking the Ice! Here Are a Few Conversation Starters When You’re in a Rut!

When you're ready to get past the surface level:

To understand your partner or friend as an individual, it is essential to acknowledge the potential differences between you two. Don’t assume that the other experiences the world in the same way you do. Learning about each other’s uniqueness will ultimately unite you. These are the questions that will help you to "grow closer and feel more connected to what our partner needs," explains Wachtel.

  1. How are you really?
  2. What would be the title of your memoir?
  3. How important is love to you?
  4. What’s the worst thing you’ve ever done to another person, and do you regret it?
  5. What is your role in your friend group?
  6. What are your siblings like/What is being an only child like?
  7. What is your love language?
  8. What are your thoughts on marriage?
  9. Do you see yourself having children?
  10. What motivates you in your career?
  11. How important is money to you?
  12. What was your first impression of me?
  13. What’s something you want to ask me but are afraid?

When you're feeling lovey-dovey:

Having sentimental conversations allow people to dissect what it is about the other that brings so much joy into their life.

These conversations are good reminders of the love between friends or partners despite the chaos of everyday life. Fleming says they help with “focusing on gratitude and the practice of appreciation.”

Talking these prompts out, no matter how much you think the other knows it, “reinforces the strength of the relationship," she adds.

  1. I was drawn to you because…
  2. I chose you because…
  3. What would you say is my love language?
  4. What can I do to make you feel more loved?
  5. What’s the fondest memory you have of us?
  6. You’re my best friend because…
  7. One thing I appreciate in you is…
  8. One thing I appreciate in us is…
  9. What is romantic to you?
  10. What would you say is the best part of dating/being friends with me?
  11. What would you say is the best part of dating/being friends with you?
  12. What’s your favorite quality of mine?
  13. When did you know you loved me?

When you want to initiate talk about sex:

You can’t have physical intimacy without having a sense of emotional intimacy.

According to Wachtel, some people feel bonded and connected through physicality, while others prefer conversation. Put simply, conversing can feel like foreplay. So, when it comes to strengthening the sexual part of your relationship, that can start with an honest convo.

  1. What’s your favorite sex position?
  2. Where’s the most random place you’ve had sex?
  3. What’s the best sex you’ve ever had? What made it so great?
  4. What's the worst sex you've ever had?
  5. What do you look for in a sexual partner?
  6. When was the last time you were tested for STDs and STIs?
  7. What are your thoughts on monogamy?
  8. How important is sex to you and what is your relationship with sex?
  9. What’s your biggest turn-on?
  10. Do you want to play a game?
  11. Do you have any sexual fantasies? If so, what’s your hottest one?
  12. Is there something you would like to bring into the bedroom?
  13. Is there anything you wouldn’t do in bed? What is it?

When you're going through a rough patch:

Having an honest conversation with someone while angry is really hard. But trying your best to dig deep when you’re in the midst of an argument can be a relationship saver.

These prompts might just be what you need to get to the bottom of the issue: “The more we chip away and unpack, understanding the defenses of the couple and the dynamics, and what’s really actually behind that is a whole other world,” says Wachtel. The sooner you tap into underlying emotions, the sooner the healing can begin.

  1. I’m hurt because…
  2. In what ways are you feeling unheard? What can I do to make you feel heard and supported?
  3. What is making you feel so hurt right now?
  4. Why are we actually having this fight?
  5. What is this fight really about?
  6. Did something earlier prompt or build to this?
  7. What are you most defensive about?
  8. How can we be more vulnerable, empathetic, and understanding to break out of this cycle?
  9. I'm confused about...
  10. One thing we can work on together is...
  11. I wish I had someone with whom I could share…
  12. How are you feeling?
  13. Do you want to find a solution?

When you want to get extra, extra deep:

Sometimes you don't need a reason to have a deep conversation beyond wanting to strengthen your relationship, says Flemming. When digging into someone’s past, make sure the setting and the timing is right.

Tip: Just ask the other person if it's a good time and place to have an important conversation. This way, the other person feels respected and safe.

  1. Is this a good time to talk about [blank]?
  2. What song always makes you feel better when you’re feeling down?
  3. What’s the hardest thing you’ve had to overcome?
  4. What’s a goal you haven’t done that you still want to accomplish?
  5. What social issue are you most passionate about?
  6. Who are the most important people in your life?
  7. What has been your most embarrassing moment?
  8. What was the hardest part of your childhood?
  9. What’s been your greatest heartbreak?
  10. What do you believe to be your greatest contribution to the world, and what do you hope it will be?
  11. What do you still feel guilty about?
  12. What do you need to forgive yourself for?
  13. Why? (Follow up with them about their answers. "Why do you feel that way?" Showing interest in their stories shows how important they are to you.)