“Getting a date is the easy part,” Sam moaned.
I wasn’t surprised. With his striking blue eyes and chiseled jaw packaged into 6 feet of pure muscle, I could definitely see dates coming easily to him. It also helped that Sam was outgoing, hilarious, and kind.
“So what’s the problem?” I asked.
“So, here’s how the last few dates have gone. I meet a girl, we like each other, we talk for hours. It’s fun and enjoyable. Then, it’s the end of the night and I feel like I’ve made another great friend and am no closer to finding a girlfriend. How do I make the conversation romantic?” Sam looks at me with the earnest curiosity of a student on the first day of class.
“Ahhh, so it’s the conversion from friend to romantic interest that you’re struggling with?” I pondered.
“Yes!! Conversion! How do I get her to talk about her heart?” Sam jumped up excitedly.
“What do you guys talk about for hours?” I asked.
“You know — what we like reading, philosophy, hobbies, where we grew up, favorite restaurants, our jobs. The worst part is I know she’s attracted to me too but after a couple of dates like that…well, it’s the friend zone for me.”
Sam was extremely well-read and a great conversationalist but the questions he was asking on his dates were probably better suited for making friends or even bonding with a co-worker than a romantic interest. Turns out, talking about the weather is not a great primer for getting sexy. So, I wrote this list of questions for all the Sams out there.
A bit of warning though — these questions are not for the faint-hearted asker or responder. Like Sam, most people are far more comfortable with extended small talk and you may even find the questions confronting when they are inevitably flipped around to you. But if you are a curious person and have an equally adventurous partner, you’re in for a fun ride. Ready?
Easing into the hard questions
As most of the questions below are quite probing, it isn’t advisable to just blurt it out like you would a small talk question. So, here are some casual openings you can use to ease into them. Start with the words in bold and you can replace the rest of it with another question from the full list.
“I loved what you wrote in your profile/what you said about the perfect cup of coffee and how much bliss that brings you. What are your peak moments of bliss this year?
“So, I recently read that most attachment styles are just an attempt to recreate a bond with a parent. I thought that was fascinating. Have you heard of attachment styles? Do you feel that statement would be true for you?”
“I’ve been thinking a lot lately about my core values that I want to create in a relationship. Do you know what yours are?
“I recently came to the realization that my love language is physical touch. Do you know what yours are?
“My brother/friend and I were just reminiscing about our childhood today and how full of love it was. Do you have any siblings? What was your childhood like?
“My friend just broke up with her boyfriend when she realized that her relationship was exactly the same as her parents. I’d never thought about how my parents’ relationship would affect mine. How do you feel about your parents as romantic role models?”
“Let’s play a game. Your fairy Godmother wants to grant you the person of your dreams. What would you ask for?”
To be clear, I’m not suggesting that the questions below are the only questions you should ask on your date. I’m simply giving you ideas for when you are ready to guide the conversation to a more romantic level.
The questions are presented in no particular order. Feel free to mix and match between categories according to how the conversation flows.
About the date
- What would you ask me for if you knew I wouldn’t say no? — A variation of this could be, “If your fairy Godmother wanted to grant you 3 wishes right now, what would you ask for?”
- What can I do to make this date a 10-out-of-10 for you? — A variation of this could be, “What can I do to make this date 10% better?”
- What was your first impression of me when you met me? Is that different now?
- How would you describe this date and me to someone else?
- What feelings are you experiencing right now? — A variation could be, “What movie reel is playing in your head right now?”
- What am I not asking that I should?
- If a movie was made about this connection, what kind of movie would it be?
- If we could magically be transported anywhere in the world right now, where would you choose for us to go?
- What do you value most about the people closest to you in your life?
- How would you describe yourself as a person? Would that change if you were describing yourself as a partner?
- What is the highest compliment someone can give you?
- Do you know your attachment style? — If you don’t know your attachment style, take this free quiz to find out.
- Do you know your love language? Do you receive and give love the same way? — If you don’t know your love languages, take this free quiz to find out.
- What is something you haven’t told anyone in a year?
- What kind of relationship do your parents have? In what ways would you like it to be the same or different?
- How did you experience love as a child?
- Who are your role models for love today? Why?
- What is your relationship like with your father and mother?
- What was your ideal relationship like when you were 16? How has it changed today?
- What is relationship bliss for you? What are your core values in a relationship? — e.g. communication, kindness, friendship, emotional safety.
- What do you love most about being in a relationship? What do you fear/hate most?
- What is something you’ve always been afraid to bring up in a relationship?
- How does a partner create emotional safety for you?
- What is your superpower in relationships? — e.g. creating a safe space for emotional expression, willingness to explore sexually, ability to work through hard conversations.
- What are your dealbreakers and must-haves? — e.g. religion and children.
- How important is love in your life? — This may seem like an unusual question but it’s not. It’s possible that someone may be more career-driven at that moment.
- What kind of touch does your body crave right now? — Surprisingly, the most common answer I have received for this has been sensual (not sexual) touch. If asked in a non-sleazy way, this can open up a great conversation about the different ways a person receives physical pleasure.
- How much have you explored your sexual fantasies? Are there any that you have or always wanted to live out?
- Would you like to be more adventurous in bed? What is holding you back? How could a partner best support you?
- What is something you’ve always wanted in a relationship but never experienced?
- When was the last time someone you loved made you really happy? What did they do?
- When was the last time someone you loved really hurt you? What did they do? How did you respond to it? Would you change that response today?
- What is your favorite thing/least favorite thing about your past relationships?
- What are the most important lessons you have learned from your past relationships?
- What would you most have wanted your ex-partners to know about you?
- What is the most common reason your relationships end?
- What have you struggled most with in past relationships?
- Is there a relationship pattern you find yourself repeating?
I encourage you to think about your own answers to any questions you choose to ask as most people will finish their response with, “What about you?”
The Most Important Tip
Sam had come to me wanting my best fail-safe tips for a great date. Here’s the most important tip I gave him — there is nothing that you can say or do that will always work because each person will respond differently to you. It’s all about attunement and alignment. The best thing you can do is accurately gauge how your partner is feeling and get on the same page as them.
That is the same advice I would give about when to ask the questions and which ones to ask. Pay attention to how they are responding to you and whether they are open to you asking more intimate questions before launching into them.
Remember, the sexiest thing you can bring on a first date is your full attention.
“Judge a man by his questions rather than by his answers.”
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