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In 2015, The New York Times published a list of 36 increasingly personal questions to get two strangers to fall in love. The list of questions, published after a strong response to Mandy Len Catron’s Modern Love essay, “To Fall in Love With Anyone, Do This”, has been taken on as a challenge of sorts; accepted by everyone between long-term couples to complete strangers.

Maybe unsurprisingly, not every pair who has answered these questions together are now happily in love, forever and ever. Convenient as “quick fixes” may be, they don’t really exist when it comes to matters of building strong romantic feelings. But what the questions can accomplish, is arguably better. They offer a concise tool to fast-track two people into experiencing shared intimacy (which has more to do with long-lasting relationships and happiness than love itself does, by the way!).

In the case of romantic relationships, higher levels of intimacy are also associated with higher sexual desire between two people. So we wondered: what could partners ask each other to deepen sexual intimacy, specifically? With the help of resources made available by professional sex therapists and leaders in sex-positive communities, we’ve assembled 36 questions to do just that.

Whether you want to open the gates of communication with each other about sex for the first time or are looking to refresh your sexual relationship, our hope is that these questions serve as a springboard for more open dialogue and deeper trust with your partner in the long term.

Set aside at least an hour with each other (it’ll almost definitely take longer), without any tight schedules or distractions. Get comfy, but be sure you’re facing each other and can easily see into each other’s eyes while you answer and listen.

Ask each question of one another back-and-forth and most importantly: be cognizant and consensual in asking these questions - no one should feel forced to answer anything that feels likes it’s crossing a line for them or brings up troubling feelings or memories*.

*Note that while many of these questions are informed by sex therapists, this is not a replacement for consulting with a professional — particularly, if you have experienced sexual trauma, you may want to seek professional assistance before delving into the questions with a partner.

Observations, Opinions, Habits

  1. 1What toys are you interested in, but nervous about trying?
  2. 2What would constitute “perfect” sex for you?
  3. 3What’s a random unique thing you find sexy in people?
  4. 4Is there anywhere you’ve thought about having sex besides the bed?
  5. 5What are 3 words that describe your favorite kind of sex?
  6. 6What do you like to do during foreplay?
  7. 7Favorite position?
  8. 8What do you wear when you want to feel sexy?
  9. 9What’s been your favorite moment from our sex life?
  10. 10Name three things you both seem to like to do during sex.
  11. 11What part of your body are you most proud of? What part of mine do you like the most?
  12. 12What’s your first memory of feeling turned on?

Dreams, Wishes, Relationships

  1. 13Do you remember your first orgasm?
  2. 14Given the choice of anyone in the world, who would you want to have sex with?
  3. 15How do you masturbate?
  4. 16Was sex discussed in your family growing up? What was the dialogue like?
  5. 17Any memorable sexual dreams?
  6. 18What gets you in the mood the most?
  7. 19What turns you on the most during sex?
  8. 20What is your usual mood before, during, and after sex?
  9. 21If it were completely up to you, how many times a week would you want to have sex?
  10. 22Where’s your favorite place to be touched?
  11. 23If you could only tell a partner one thing about what you want during sex, what would it be?
  12. 24Share something you were once afraid of trying, but ended up loving.

Memories, Deeper Thoughts, Perspectives

  1. 25Anything you’d regret not trying?
  2. 26How do you define “sexy”, for yourself? When do you feel sexiest? When do you find me to be sexiest?
  3. 27What role do you want sex to play in your future?
  4. 28How and when did you know you were attracted to the sex/gender you’re attracted to?
  5. 29What do you think about when you masturbate?
  6. 30How do you think our sex life will change through the years?
  7. 31Share a personal problem or barrier and ask advice on how your partner would handle it.
  8. 32Share an embarrassing sexual moment or thought (or one that you think is embarrassing).
  9. 33Is there anything about sex that feels inconvenient or anxiety-inducing to you?
  10. 34What’s something you’ve fantasized about but never tried?
  11. 35How do sex and intimacy differ, in your mind? What does it look like when they overlap?
  12. 36What are our sexual strengths and weaknesses, as a pair?
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