100 Questions to Ask Your Boyfriend

From LoveToKnow Dating

Here's a challenge for you: come up with 100 questions to ask your boyfriend. What kinds of things could you learn - not only from his answers, but also from the questions you chose to ask?

Getting to Know Each Other

It is hoped that any relationship will be built on communication and good to-and-fro questions and answers. However, taking the time to ask these questions deliberately, with intent, can be a way for you to see a side of your boyfriend that you might not expect to see.

It may be easy to come up with 100 questions to ask your boyfriend, but if you are having some trouble, here are some categories and "seed questions" that might inspire you.

Basic Questions

The basic questions are like the logistical framework of your boyfriend. They start with things like "What is your favorite..." and then go on to list something innocent and innocuous. Start with the simple things - ice cream, color, holiday, car - and then get into more unusual questions. Instead of, "What's your favorite TV show?" try "What's the funniest thing your favorite TV character ever did?" Keep these factual; you can use them later on when it's time to buy a gift, or make him happy when he's feeling down by showing up with a poster from his favorite movie.

Romantic Questions

You may be tempted to ask basic romantic questions like "Do you love me more than you did your last lover?" but keep in mind that men have been conditioned to regard that - and many other questions involving romance - as traps designed to make them say something they will regret. You need to make sure, if you are asking questions about feelings, to make them feel safe and not put on the spot. Questions about concrete moments will be easier than abstract emotions: What reminds you of me when I'm not around? or If you could take me on a romantic vacation anywhere in the world, where would we go? works better than, How do you feel when you look in my eyes? You should throw in a few abstract questions at the end, just to see if a warm up could get him to open up. However, make sure you don't get upset at his answers, because if you get angry, it will be the last time he answers questions like that.

Naughty Questions

One of the most important conversations a romantic couple can have is about their sexual histories. Using this question game to help make it a fun and even titillating experience can be a way to take the awkwardness out of the conversation. For example, a question like "What's your favorite brand of condom?" can be a way to broach the subject of safer sex. Likewise, "What's your most embarrassing moment during sex?" helps take some of the stigma out of sex and puts it into a positive, humorous light.

Family Questions

You can learn a lot about your boyfriend from his memories of his childhood and his family. These questions can often be the most emotional, because you are taking him back to the formative years - which can be both good or bad, wistful, painful, or happy. Again, it's important with all of these questions to make him feel as though he can safely express himself honestly - this is not the time to be judgmental, and certainly not to run a guilt trip about anything. Ask about favorite memories of people in the family, or earliest memories. Which member of his family does he think he is most like? You may be surprised at the answer.