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21 Questions to Ask a Guy to Start a Conversation

Choose 21 questions to ask a guy to deepen your relationship or help you start a conversation to get to know him better if you are just starting out.   

125+ “How Well Do You Know Me?” Questions for Couples

What do you do when you want to reconnect with your partner in a simple way? Ask ” how well do you know me questions” on your date night or evenings together !

What are the Best Date Night Questions?

We have over 90 date night questions, some of which are funny and deep but all are insightful. Most of our date night questions  are perfect for longer term or married couples. 

130+ Ice breaker Questions & Texts to have Amazing Conversations

We love these ice breaker questions that make our conversations easier and much more interesting.   

Funny Would you Rather Questions to ask Couples and Friends

We put together plenty of questions to ask your partner or friends, some are deep and others are funny would you rather questions. 

First Date Ideas + All Your First Date Questions Answered

We want to make your first date as easy as possible so we answered many of your common questions. We also list first date ideas besides just the usual “grab a drink” option.   

73 First Date Questions That lead to Insightful Conversations


Questions are the perfect way to get to know someone and our first date questions are a fun way to do just that!   

175 Fun Questions to Ask to Get to Know Someone

These fun questions can create insightful conversations. We have questions for friends, questions for guys & girls, first dates and someone that you like.