11 Questions To Ask The Guy You’re Dating To Get Closer

Asking generic questions like “how was your day?” “have you eaten?” and “what’s your favorite color?” can get old and monotonous really fast. If you want to build real intimacy with your partner, you’ve got to start digging a little deeper. You need to ask questions that help you create a meaningful connection and also discover new and interesting things about each other. I suggest trying one of these.

  1. Is there anything you wish we did together more? There might be something that your boyfriend wants to explore or get to share with you. It could be a thing you both did together one time or something you’ve never done together. This way you get to find out what his favorite couple’s activity is and come up with fun date ideas.
  2. What would you do if won the lottery? How your partner views money and spends it when they have a ton of cash can say a lot about who they are. Maybe he’s the kind of person who’s going to buy a mansion, fancy cars, and a boat. Or, he might be the guy who uses his winnings to send underprivileged kids to school. Or he might quit his job, travel the world, and paint. Whatever his answer, you’re going to have a lot of fun with this question.
  3. Who was your first love and why didn’t it work out? Our first loves always have a place in our hearts. They’re an indelible part of our history and they influence a lot of the relationships we have later in life. This question will help you understand your partner’s romantic life before you came into the picture. You’ll also learn about what he loves or hates in a partner or relationship.
  4. What’s the most embarrassing thing that ever happened to you? Almost everyone has one or two moments that made them wish for the ground to open up and swallow them. Learning about the embarrassing things your boyfriend has done will bring plenty of laughs a healthy dose of vulnerability.
  5. If you could go back in time, what would you change from your past? This question will help you see the wounds, regrets, or wishes that your partner carries with them. It might be a difficult subject to talk about, but it’ll expose a side of him that you might, help you understand him better, and bring you closer.
  6. What’s your idea of a perfect weekend? Weekends are for relaxation and everyone has their own way of unwinding. Hearing about his idea of a perfect weekend can show you some of the things that are important to him and help you see how he likes to de-stress. You can then take his idea and bring it to life some other time to make him feel special and loved.
  7. Did you have any role models growing up? The people your partner looked up to as a child, teenager, or young adult must have had a huge influence on his life. It could explain why he holds some of the values he has and how he came to be the man he is today. It’s a great way to learn more about the people and things that he holds in high regard.
  8. What’s the biggest lie you’ve ever told? Is your boyfriend the kind of person who values honesty or the kind who tells lies without thinking twice? How he answers this question will reveal where he stands on dishonesty. But there’s also a chance that he’ll tell you about a lesser lie instead of admitting the biggest one. Just listen to the story and watch how he tells it.
  9. Are you close to anyone in your family? Some people aren’t close to their families, but for some their siblings or parents are everything. It’s always a good idea to know what family means to your partner and how he relates with the people who define a huge chunk of his life.
  10. What’s your favorite or worst childhood memory? This is a good inroad into your boyfriend’s childhood. Whatever memory he shares will be a special, little part of him. You might also get some ideas for how to create more wonderful memories for him to recreate the feeling of the good memory or replace the bad one.
  11. What are you most afraid of? I am incredibly terrified of failure and poverty. They’re the biggest driving forces in my life. I cannot accept a life in which I have to struggle to afford basic things. Knowing what fears keep your partner up at night can enable you to help him overcome it or support him better when the fear arises.
A girl preoccupied with living her best life even when it's uncomfortable to do so. She spends a lot of time with her thoughts. She hopes you enjoy reading the results of those thoughts.