The start of a relationship is often filled with sleepless nights spent getting to know each other and talking about your lives, dreams, likes, and dislikes. You’re filled with curiosity and questions to ask your partner.
Fast forward past the honeymoon phase and that sense of novelty is replaced with a sense of comfort and familiarity. Feeling comfortable with your partner isn’t a bad thing — it can provide a sense of safety and security — but it’s all too easy to let boredom set in.
“As a relationship progresses and our busy lives kick in, few couples make time for meaningful conversations,” says Dr. Jacqui Gabb, a professor of sociology and intimacy at The Open University and Chief Relationships Officer at Paired.
“We talk about schedules, who cleaned the sink, how to navigate shared desk space — but not about our everyday stressors, challenges, or vulnerabilities.”
In her research, Dr. Gabb found that couples who make time for intimate conversations build a foundation from which connection, intimacy, and trust can thrive.
So, we put together 100 intimate and insightful questions to ask your partner on your next date night, to keep those relationship foundations strong and stable.
How can I help out more around the house?
How do you think you can help more around the house?
Of the special occasions that we’ve celebrated together, which has meant the most to you?
When do you have the most fun with me?
When do you find me sexiest?
What do you need from me right after an argument?
How would you define a successful relationship?
What’s your favorite kind of physical affection?
What’s your least favorite kind of physical affection?
What’s one thing that has improved our relationship?
What’s our greatest strength as a couple?
What aspect of our relationship could we work on more?
How long do you think sex should last?
Which of our individual strengths brings the most to our relationship?
What sex act are you open to trying, but haven’t yet?
Do you think foreplay is important?
What scares you the most about relationships?
In what ways do you think we’re most compatible?
In what ways do you think we’re most incompatible?
What are the most important items on your bucket list?
What does relationship security mean to you?
Do you think sex should be passionate, fun, or romantic?
What do you remember about the first time we met?
What adventure would you like us to take together?
What’s one thing I introduced you to that you really like now?
What’s one thing I do that always turns you on?
What’s one of your favorite memories we’ve made together?
What song reminds you of our relationship?
When did you know you had feelings for me?
What physical object makes you think about me the most?
Which do you prefer: waking up together, or falling asleep together?
What’s the biggest challenge we’ve faced together?
What do you think is more important for a relationship: physical or emotional attraction?
How much sex do you want to be having?
What are our biggest strengths and weaknesses as a couple?
What could I do for you that I don't already do?
Aside from sex, what other ways do you like to be intimate?
What romantic gesture did you wish I did more?
What’s one quality we have in common?
What about me has surprised you the most?
What’s your favorite compliment to receive?
What’s your favorite movie when you need a good laugh or have had a bad day?
If you could choose any superpower that would change our relationship, what would you pick?
What’s your view on sex in long-term relationships?
Are there any deep questions you have always refrained from asking me?
Do you know what my love language is?
What was the moment you felt like you knew me on a deeper level?
What’s your biggest fear when it comes to our relationship?
Do you think that we have a healthy relationship?
Would you consider me as your best friend?
Do you know my childhood celebrity crush?
What are your main dealbreakers in a relationship?
What’s your favorite thing about our relationship?
Do you have a guilty pleasure when I’m not around?
What are the small things you remember about our first date?
Do you think this relationship has helped to heal your insecurities?
When was the last time you cried? Was there anything I could have done to help?
What do you think is the best way to handle a break-up?
What would you consider to be a perfect day for us?
Do you have a dream vacation destination?
Would you consider us compatible?
How important do you consider emotional intimacy in a relationship?
Are you more of an introvert or an extrovert?
What famous person do you think that I look like?
Describe your favorite childhood memory to me.
What was your first impression of me?
What was your favorite date that you’ve ever been on?
Do you have a favorite book that you’ve read over and over?
How would you rate our first kiss on a scale of 1 to 10?
Do you have a favorite place to go when you’re feeling low?
What’s the happiest memory that we’ve ever shared?
Do you ever think about your last relationship?
How do you think couples can keep the spark alive in a long-term relationship?
Do you feel like you’ve grown up since high school?
Describe your perfect date.
What’s your biggest pet peeve? Have I ever done it?
Who was your role model growing up?
Could you see yourself spending the rest of your life with me?
How soon is too soon to say ‘I love you’ in a new relationship?
What is your favorite childhood TV show?
How can I help you look after your mental health?
Would you prefer to live in New York or Los Angeles?
What is your ideal age to settle down?
What do you think about trying out trending fashion choices?
How important do you think compatibility is in a relationship?
What do you think is the best way to handle conflict in a relationship?
What boundaries do you think are important in a relationship?
How do you think couples should handle finances in a relationship?
Have you ever felt like I wasn’t listening to you?
Do you have a five-year plan?
How important do you think kids are for our future?
What are your thoughts on setting limits on our social media use?
Do you think scheduling sex is a bad idea?
Would you ever consider couples therapy?
How much do you know about your attachment style?
Do you have any turn-offs in a relationship?
Have you ever had any dreams about me?
What do you consider cheating in a relationship?
What activities do you think we could start doing together?
What are your thoughts on using sex toys in the bedroom?