When your relationship progresses past the first few dates or you feel it’s an appropriate time to ask personal questions, you might be at a loss on topics to talk about that bring out more in-depth or meaningful conversations. Understanding when and how to start a conversation with your boyfriend that opens him up to his personal life can be tricky, but here are some ideas to get you moving towards more serious discussions.
Understanding Each Other’s Personalities
To get close to your boyfriend, it’s important to get to know each other’s unique personalities. To do so, you can ask deeper questions, listen intently to his response, and share your own experiences with him. Delve into these topics after you’ve spent some time together and have made it past the very beginning stages of the relationship. Here’s what to talk about with your boyfriend to get to know his personality:
- Processing information: Get to know what makes him tick and how he processes information. You can ask, “When you have a big decision to make, how do you decide what to do or how to handle the situation?”
- Childhood: Ask him about his upbringing and who he is closest to in his family. This can give you some information about how he views relationships, and how relationships were modeled to him during his childhood.
- Unhealthy relationships: Ask him if there’s ever been a time where he struggled with an unhealthy relationship and what that was like for him.
- Good relationships: Explore what he thinks makes a solid relationship and what factors contribute to not so good relationships.
- Friendships: One of the best ways to get to know someone’s true self is to find out information about their closest friends. Ask him what his best friends are like and how they like to spend time together.
- What he notices: Ask him about what he tends to notice first when he sees a person, a work of art, and something in nature.
- Giving things up: Ask him if he’s ever had to give something up and what that was like for him.
- Regret: Talk to him about if there’s anything he has done or missed out on that he regrets.
- Pride and values: Talk about a time where he felt super proud of himself and why. This will give you some insight into what he values.
- External vs. internal tendencies: Discuss whether he’s an internal or external processer and if he’s ever had any difficulty with how he processes. You could ask, “Have you ever blurted something out that you didn’t mean to say because you were processing things aloud?”
Conversations About His Family and Future
One way to really get to know your boyfriend is to encourage him to chat about himself. Ask your boyfriend about his childhood, his parents and siblings. Have him share memories, both good and bad, about growing up. You’ll find that by doing this, you’ll have a better understanding of him and the person he is today.
- Who is your favorite relative?
- Do you get along with your family?
- Do you want kids?
- What is the best piece of advice you received?
- What is the craziest thing you’ve ever done?
- Where do you want to go to college? Or where did you go to college?
- What is your dream job?
- Where do you see yourself in five to 10 years?
- What are your thoughts on marriage?
Sometimes the best conversation starters can be just talking about yourself. Tell him about a favorite aunt or that crazy road trip you took with your grandmother. Give him an opportunity to share a similar story.