25 pillow talk conversation starters for deeper connection

There’s nothing more intimate than curling up in bed together and chatting before you fall asleep. Amanda Denes, a relationship researcher, said:  “During pillow talk, couples may feel more comfortable opening up about their stresses, …

There’s nothing more intimate than curling up in bed together and chatting before you fall asleep.

Amanda Denes, a relationship researcher, said

“During pillow talk, couples may feel more comfortable opening up about their stresses, feelings, and hopes for the relationship, and this openness may trickle over to other, non-sexual contexts.”

Of course, this isn’t just restricted to couples. Kids often ask interesting — or perplexing — questions before bedtime, as that’s when they are the most relaxed. 

Whether you’re winding down with your fam jam or with your other half, here are questions to spark some conversational magic: 

Small talk 

  1. Are you sleepy?
  2. Would you like to chat for a bit before we sleep? 
  3. Can I give you a massage? // Can I get you a cup of milk/water? 
  4. How was your sleep last night? 
  5. How was your day? (Anything you didn’t get to share with me?)

These questions help you gauge if they are open to talking more — your loved one might just wanna crash without any chat. 

Questions for couples 

Given that you probably don’t wanna fight before sleep, I brainstormed questions that are imaginative and thought-provoking, but aren’t too heavy 🙂 

Fun questions 

  1. What would be the perfect theme song for our relationship? 
  2. What’s your no. 1 thing on our relationship bucket list?
  3. If we entered the same dream, where would we be and what would we be doing? (More dreams conversation starters here)
  4. If we time-traveled to the past, which era and country would we be in? 
  5. If the world was going to end tomorrow, how would you want to spend our last day together?  

Deep questions 

  1. When did you find me attractive recently? 
  2. When do you feel the happiest together? 
  3. When do you feel most loved by me?
  4. What’s one thing that you’ve been meaning to do together, but haven’t been able to? 
  5. What would make this year unforgettable for us/our relationship? 

For family

Fun questions 

  1. What would be the perfect theme song for our family? 
  2. What’s your no. 1 thing on our family bucket list?
  3. If we were on a one-year family vacation, where would you want to go and what would you want to do? 
  4. If our family was an animal kingdom, what animal would you want to be and why? 
  5. If we swapped bodies, what would be the first thing you do as the parent/child/older/younger sibling? 

Deep questions 

  1. What makes our family awesome?
  2. What makes you smile when thinking about our family? 
  3. What’s the one thing that reminds you of our family?
  4. When do you feel most loved by the family? 
  5. What would make this year unforgettable for us/our family? 

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