As you progress in your relationship, you will start to bond together naturally and at a comfortable pace. You move on from flirting to long and meaningful conversation. Gradually, you start to share important conversation, like facts about your upbringing or your goals in life.
Of course, spouting out this highly sensitive information to your date – without being asked first! – is considered rude. Or at least a little strange! “Socially awkward” they might call it, because it shows that a person doesn’t seem to understand social cues.
This is precisely why women (or men) who start unloading all their personal baggage on a first date usually get dumped. They’re too intense. Or they’re too obsessed with their ex. They come across as clingy or even desperate.
Everybody wants to bond but it’s very important to NOT rush things and to proceed at a pace that’s comfortable for both of you.
One of the best ways to bond naturally is to ask just a few deep relationship questions for every date. You can ask additional questions for clarification, but you should avoid playing 20 questions and finding out the guy’s whole life story in one afternoon. It’s far more enjoyable to spread these questions out over several dates, all the while making small talk, flirting, and talking about day-to-day things.
The question is how do you ask for a man’s life story without sounding so cheesy about it?
Feel free to steal from our list of relationship questions that will get him thinking, talking and sharing.
- What’s your favorite quality about yourself?
- When you’re in a bad mood or having a bad day, what’s the best way to deal with you?
- What quality in a person is the most important to you?
- How did you parents get along?
- Truth or dare, ask me anything you want and I’ll answer you truthfully.
- What’s your favorite holiday and why?
- What’s the best relationship advice a family member or friend has ever given you?
- What was the proudest moment of your life?
- When in your life do you remember feeling the most frightened?
- Do you like the grand romantic proposal in public or the quiet alone proposal?
- How do you get along with your exes?
- Are you more proud of your good looks or intellect?
- How do you define cheating in a relationship?
- What is happiness to you?
- Do you think partners should share all their secrets or keep some to themselves?
- What’s one thing about me you would change?
- What’s one of your phobias?
- What kind of parent would you be?
- What’s the most important lesson to teach children?
- What did your last relationship teach you about love, about life?
- What is a relationship deal breaker for you?
- What are some of your unpopular opinions?
- What religious persuasion is your family? Do you agree?
- What political affiliation is your family? Do you agree?
- What was your first impression of me?
- What kinds of sexual fantasies are you into?
- What would the book of the story of your life be titled?
- What actor or character would play you in a movie?
- What’s a book that changed your life (or at least came close to it)?
- What is one place in the world you’ve always wanted to visit?
- What’s the funniest meme you’ve ever seen?
- What’s a movie or TV show that makes you laugh out loud?
- When’s the last time you cried?
- What’s your favorite movie or TV show of all time? Why so?
- What is your dream job?
- What is something on your noble bucket list?
- What is something on your guilty pleasures bucket list?
- What do you think happens after we die?
- Have you ever seen anything paranormal?
- What’s your funniest intoxicated story?
- What’s the most embarrassing moment of your life?
- What is a lesson your parent(s) taught you that you still remember?
- What person or movement do you think is especially courageous?
- Who were your childhood heroes?
- What is your favorite meal (and dessert) of all time?
- What has been the best day of your life so far?
- What is your favorite video game or board/card game?
- If you could give one message to the whole world, what would it be?
- What is your spirit animal? Or favorite type of pet?
- What does falling in love for the first time feel like?
- Have you ever been bullied? What did you do?
- What’s something you’ve never told anyone else before?
- What’s the most challenging part of dating someone like me?
- If you have a billion dollars what would be the first five things you would do?
- What accomplishment are you most proud of in your life?
- What is another language you would like to learn and why?
As you can see, the secret to asking effective questions is to evoke positive emotion from him. Get him excited about the topic. Ask about his favorite memories or his top passions in life. Ask him about his personal views and his life goals. These questions allow him to feel like the “star”, the center of attention.
The setting is also very important. Make sure to have a quiet setting where he can speak freely, without causing a scene, and without being interrupted by others. Be kind and patient when he answers difficult questions. Don’t ever judge him. Let him feel safe in your presence, like he can tell you anything.
That’s what he wants. Over time he will start to figure out that you make him feel good about yourself and that you understand him in a way that most other people don’t. That’s the key ingredient when it comes to love: focusing the spotlight on him!
One Deep Question You Can Answer Right Now
These questions help you learn a lot about him. There’s one big question you might still be asking yourself, though: does he love me?
My free quiz answers that one, based on how he acts. It takes about a minute.
Take the “Does He Love Me?” quiz »
