371 Deep Questions to Ask Someone [Updated for 2022]

Check out these 371 deep questions to help you get answers to reveal a person’s true character.

One of the best ways to get to know someone better is by asking open-ended, deep questions. Even though many questions might sound generic and it may only incite small talk, the responses are usually very revealing. They give you a glimpse into a person’s true nature. Sometimes, answers to personal questions will even reveal … Read more

125 Questions to Ask a New Friend to Quickly Get to Know Them

questions to ask a new friend | questions to ask a new friend online | questions to ask your friends about yourself

I am sure many of us can remember the days of being a child and quickly making friends with others our age.  We bonded over whatever activities we mutually enjoyed being involved in.  Many of us bonded over toys, sports, playing cards, or the love of playing in the mud.  Yes, life was much simpler … Read more

325 Personal Questions to Ask a Guy to Start a Deep Conversation

personal questions to ask a guy | deep personal questions to ask a guy | personal questions to ask a guy to get to know him

As you’re getting to know someone who you are seriously interested in, it’s a good idea to have some “go-to” personal questions to ask a guy.  These inquiries can be exciting, deep, sexy, but they should all be asked in an effort to get to know him better. So it’s important that you know what … Read more

125 How Well Do You Know Me Questions for Friends and Family

how well do you know me questions | how well do you know me questions for family | unique how well do you know me questions

You probably think that you know your close friends and family members very well… but do you? The best way to find out is to play a little game of “20 Questions”… or in this case, 125 Questions! We’ve put together a list of questions on a variety of topics. Depending on who you’re playing … Read more

212 Good Questions to Ask a Girl You Like in 2022

good questions to ask a girl | flirty questions to ask a girl | questions to ask a girl to know her better

Are interested in a specific girl? Typically when you fall for a girl, you’ll want to know everything about her. You may be overwhelmed because you don’t know where to begin. The best place to start is to ask questions about herself. Which opens the door for a deeper conversation and a meaningful relationship. So … Read more

175 Fun Questions to Ask Your Boyfriend to Know Him Better

questions to ask your boyfriend | juicy questions to ask your boyfriend | romantic questions to ask your boyfriend to make him laugh

I think we can all agree that it is of the utmost importance to know all we can about our partner.  When in a dating relationship, the hope is that it could potentially turn into something more serious and permanent. No one wants to become wholly committed to a person and later find out that … Read more

101 Would You Rather Questions for Couples to Liven Up Date Night

would you rather questions for couples | would you rather dirty questions | would you rather questions for boyfriend

Have you ever been on a date and the conversation has gone stale? You can’t think of what to say next, or your date is being quiet. Whether you’re on a first date, or you’ve been together a long time, date conversations can lag from time to time. It’s not your fault.  It happens.  Life … Read more

171 Random Questions to Ask People Throughout Your Life

random questions to ask | random questions to ask funny | random questions to ask people

As you go through life, you’ll meet a lot of different people. Talking with others can help you grow as a person. Equipping yourself with an arsenal of random questions to ask people is a great way to spark interesting and enlightening conversations. They can also help you with personal and professional success. What is … Read more

71 Open Ended Questions Examples for an Engaging Conversation

open ended questions examples | open ended questions examples for conversations | open ended questions to ask

Meeting a stranger for the first time can be awkward. Yet, we are all strangers until we really get to know each other better. Sometimes, the only way to really get to know someone is to ask questions. That said, knowing which questions are appropriate and which will give you some insight into the other … Read more