Say goodbye to boring conversations and explore our list of flirty, funny questions to ask a guy over text.
Roast Founder, Dating and AI Expert
Updated January 1, 2025
You have started liking a guy, and now you want to know them better and build a strong relationship with them. Conversation starters and pickup lines are the best way to impress your potential match, new crush, friend, or possible future partner.
The right questions can help you turn a random message into a memorable exchange of thoughts, helping you uncover common interests, quirks, and deeper layers of personality. In this article, we'll guide you through a treasure trove of thought-provoking questions to ask a guy over text.
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Table of Contents
Here is the outline of the article, feel free to jump to the section that interests you the most.
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Not the best texter?
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Asking questions over text is a great way to get to know a new person and build a deeper connection. Whether you are looking for a new friend or a romantic partner, asking thoughtful and interesting questions can open up the conversation and help you learn more about the person you are talking to.
Remember that it’s also important to actively listen and respond to what the other person is saying and share some personal information about yourself.
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Ben is one of the best Dating Experts I've ever met and one of the few that cracked the algorithm of online dating. Every week, Ben is publishing new articles on ROAST, helping 20M+ of people to get more matches, dates, and find the one!
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