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20 Questions to Ask a Guy When Dating

Finding Mr. Right ain’t easy. When you’re getting to know a new fella, asking the right questions is one way to figure out if he’s a good match. We’ve got 20 questions to ask a guy when you start dating to help you decide if he’s worth your time.

You’ve locked eyes across the room, had an awesome first date, and now you’re wondering if this new guy is someone you want to get serious with. Before you go falling head over heels, it’s smart to find out a bit more about him with some strategic questions.

Asking the right questions when dating can help you understand his values, interests, personality, and more. You’ll get a better sense of whether your new beau is someone you can truly connect with. Plus, you don’t want any big surprises down the road!

We’ve rounded up 20 great questions to ask a guy when you first start dating. Mix and match them for a natural conversation. Pay attention not just to his answers, but how comfortable he seems opening up to you. A great connection is built on mutual trust and understanding.

The Best Questions to Ask a Guy When Dating:

  1. What do you enjoy doing in your free time?

This opens the door for him to talk about his hobbies, interests, and how he likes to spend his time. His answers will hint at the type of lifestyle and passions he has. If your interests align, that’s a good sign!

  1. What are you most passionate about?

Dig deeper to find out what really gets his motor running. Maybe it’s hiking, volunteering with kids, reading sci-fi novels, or playing poker with his buddies. You’ll get insight into his character and what he finds meaningful.

  1. What are some of your short and long-term goals?

His ambitions and aspirations for life say a lot about who he is. Watch for whether he has solid plans and if your visions for the future seem compatible.

  1. What were you like as a kid?

Taking a walk down memory lane offers a glimpse of his childhood personality and values. Find out what he was into as a tyke – sports, music, science projects? See if you can picture little him.

  1. What is your favorite quality about yourself?

How he sees himself reveals a lot. Listen for attributes like kindness, integrity, sense of humor, determination, or creativity.

  1. What is your biggest flaw?

A humble guy who can admit imperfections or areas for improvement is a keeper. Pay attention if he flies off the handle or blames others. Red flag!

  1. How did your last relationship end?

This opens the door to discuss past dating experiences. It also reveals how gracefully he can reflect on relationships that didn’t pan out. Make sure no bitterness lingers.

  1. Do you have any pet peeves?

Maybe he can’t stand people chewing loudly or folks who are chronically late. Take note, especially if any of his pet peeves apply to you!

  1. Who has impacted you most in life?

Listen to see who he admires and if he has deep connections with mentors, friends or family who’ve shaped him. Values and influences tell you a lot about a guy.

  1. What makes you laugh the hardest?

If you both think fart jokes are the height of hilarity, you probably have similar senses of humor. Laughter is one of the best connectors for a couple!

  1. What is your relationship like with your family?

This reveals his family values and how he interacts with parents, siblings, and relatives. Are family ties important to him? Red flags include bad-mouthing family or admitting to serious family rifts.

  1. Do you have any life experiences that have shaped you deeply?

Maybe he traveled abroad, overcame an illness, or grieved a great loss. Key experiences reveal emotional maturity and depth of character.

  1. What are some of your fears or insecurities?

His ability to confide deeper vulnerabilities says a lot about his confidence in you and emotional availability. If he shuts down, that’s revealing too.

  1. What are your spiritual beliefs?

Even if you have different beliefs, you want someone respectful. Watch if he belittles your views. But differences can lead to growth.

  1. What do you think makes a relationship successful?

His attitudes about love, communication, romance, and partnership provide the scoop on what to expect from him as a boyfriend.

  1. How do you handle disagreements?

Pay close attention to his conflict style. Healthy answers include open communication, taking breaks to cool down, compromising, and even humor.

  1. What did your past relationships teach you?

Notice his ability for self-reflection. Does he take responsibility for past relationship troubles or always blame the other person? Huge distinction.

  1. Where do you see yourself in 5 years? 10 years?

Get an idea if you have aligned visions for the future when it comes to career, family, travel, goals. Opposite answers aren’t necessarily dealbreakers but provide insight.

  1. Do you want kids someday?

Better to be on the same page sooner than later about big topics like children. If you differ, can you find common ground?

  1. What other questions do you have for me?

By flipping the script, you invite him to ask you some questions and spark meaningful two-way sharing. What he asks also reveals a lot about him.

In Closing

When you start dating someone new, asking the right questions helps you sniff out any dealbreakers and gauge whether he’s a good match. Mix serious and fun questions for a balanced chat where you both open up.

Pay attention to his reactions, too – is he engaged, a good listener, does he ask questions about you? The new dating questions game can feel a bit awkward, but it’s a crucial way to gain insights about each other. Before you get in too deep, you want to know you’re on the same page about the big stuff.

Keep the conversation flowing and have fun getting to know each other. The right questions can uncover shared values, passions, and interests that light that spark between two people. So don’t be afraid to dig deep – asking meaningful questions when dating leads to the best connections. Give this list of 20 questions to ask a guy when dating a try!

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