123 Killer Conversation Starters With A Guy For Any Situation 2023

Updated on

Conversation Starters With A Guy
100+ Killer Conversation Starters With A Guy For Any Situation 2023

If you don’t have the right set of conversation starters with a guy that can lead to a crappy conversation especially on a first date or with a crush.

You need ice breakers that are funny, naughty, flirty, and light-hearted questions to make him smile as well as deep questions to know him better.

Don’t worry, I have compiled questions that are conversation starters with a guy for any situation (crush, boyfriend, or friend) to save you from awkward silences.

Moreover, these conversation starters for a guy are perfect to break the ice. Whether you just met a guy online or just dating a guy and looking to keep the conversation flowing!

Conversation Starters With Boyfriend To Grow Closer

“What would be the absolute perfect day?”

“What did you learn a little too late?”

“What are you too hard on yourself for?”

“How often do you feel utterly worn down?”

“If money was no object, where would you live?”

“Who was the most toxic person you’ve known?”

“What habits do you have that annoy other people?”

“What makes you nervous?”

“What makes you angrier than it should?”

“What movie was so sad that you will never watch it again?”

Related: 34+35 Flirty & Dirty Questions To Ask A Guy: Turn Him On 2023

“What are the two biggest lessons you’ve learned from previous relationships?”

“What gross and unhygienic things do people do that bother you?”

“What habit do you have that you think not many other people have?”

“What do most people overestimate or underestimate about you?”

“What is something you probably should do, but will never do?”

“What was the best thing about how your parents raised you?”

“What do you most look forward to about getting old?”

“What is the biggest sign of weakness in a person?”

“What’s something you tried really hard to like but just couldn’t?”

“What makes you different from most people?”

Related: 100+ Extremely Sexy Names To Call Your Boyfriend That Are Flirty 2023

“What was the best mistake you’ve made? A mistake that turned out really well.”

“How do you feel about pets and animals?”

Conversation Starters With Your Crush That Go Beyond “Hey”

“What was the best year of your life so far?”

“Do you like flirting?”

“What’s your favorite thing to do on the internet?”

“What do you spend most of your time doing?”

“What do you spend way too much money on?”

“What do you judge people for most often?”

“What’s your favorite thing to shop for? Why?”

“What’s the best compliment that someone can receive?”

“What’s something you can do that most people can’t?”

“How do you calm yourself down when you are angry?”

Related: 130+ Best icebreaker questions to get to know someone 2023

“What is your worst getting trolled story?”

“What do you find hilarious but most people don’t find funny?”

“What was the most beautiful view you have ever experienced?”

“What event small or large has changed the course of your life the most?”

“What is something you have read or heard that has stuck with you for a long time?”

“What’s something that people go on and on about, and you just can’t take sitting through?”

“When was the last time you tried to do something to look cool and it ended in utter embarrassment?”

“What is the most cringe-worthy thing you have seen someone post on social media?”

“What is the most ridiculous rule you have to follow?”

“What bullet have you recently dodged?”

Related: 52 Unique Nick Names To Call Your Crush Guy (boy) 2023

“What country do you not know the location of even though you should?”

“What do you have a hard time with but most people find quite easy?”

“What’s the most impressive skill you have?”

“What would your parents be surprised to learn about you?”

“What superpower would you have for one day?”

“Who knows you the best?”

“What was your favorite TV show as a kid?”

“What’s the first thing you’d do if you were the opposite s*x for one day?”

“What kind of music are you into?”

“What type of movies do you like?”

Related: 88 Best Would You Rather Questions For Your Crush To Spark The Conversation 2023

“What’s your favorite food/restaurant?”

“Do you like cooking?”

“Where do you wish you could go?”

“Do you have any hobbies?”

“What was your hometown like?”

“What do you usually do when you hang out with your friends?”

“What kind of jobs have you worked at?”

“What accomplishment are you most proud of?”

“What is the next big thing you want to accomplish?”

Deep Conversation Starters With A Guy To Know Him Better

“What is your opinion on giving back to society?”

“What is the meaning of family to you?”

“What do you like about your best friend and why?”

“Who is your role model in your family?”

“How important is my career to you?”

“Who is it that you look up to in your life and why?”

“Who was your first high school crush?”

“What do you think is the best quality, in you?”

“What is it that you like the most about me?”

“Do you have any secrets in life that you have kept from me?”

Related: 31 Deep Questions To Ask Your Boyfriend To Bring Him Closer 2023

“What is your opinion on transparency between couples?”

“What is being successful in life mean to you?”

“What is your worst fear?”

“What are you grateful for in life?”

“If given a chance, will you choose someone else as your partner?”

“Who is emotionally closer to you? To whom do you relate?”

“What is your most embarrassing moment to date?”

“When did you feel happy recently and why?”

“Do you find yourself attractive?”

“If all crimes are made legal for a day, which offense are you likely to commit?”

Related: 107 Killer Truth Or Drink Questions For Girls/Guys 2023

“What is your biggest regret in life?”

“Do you think cheating on your spouse is ok as long as you are not caught?”

“When was the last time you cried? What can I do to make you feel better at such times?”

“What is your opinion on equality between partners?”

“Are you willing to support my career once we have kids?”

“Name a bad habit which you got rid of?”

“Name three people whom you value the most in your life?”

“What is your motivation to get up and go to work each day?”

“Did you experience failure in life? If yes, how did you manage to get back on your feet?”

“What is the most significant lesson life has taught you?”

Related: 138 Best Would You Rather Questions For Couples Ever 2023

“Family, money, friends what is the order of priority for you?”

“What are the three qualities in you which you want your children to inherit?”

“Who is your support system?”

“What is the best advice you have received to date?”

“Do you ever regret being in a relationship with me?”

“What change did you see in yourself after being in a relationship with me?”

“What is your deal-breaker in a relationship?”

“If at all we are on the verge of a breakup would you try to get back?”

“When did you feel respected/ disrespected by me?”

“Did I hurt you anytime? If yes, how can I avoid doing it?”

Related: 80+ Compliments For Men: They Would Love To Hear 2023

“What makes you feel appreciated in our relationship?”

“Do you feel we communicate openly in our relationship? If no, how can we improve it?”

“Do you think you have the freedom to be yourself in our relationship?”

“What made you feel I am the one?”

“What is marriage to you?”

“Do you believe in life-long commitment?”

“What are your future plans with me?”

“What is the best compliment you received from me?”

“Who is the best couple in your family and why?”

“Which love story would best describe our relationship?”

Related: 47 Insanely Flirty Comments For Him On Instagram 2023

“To whom do you owe your success in life?”

“What is that you are expecting from me?”

“Did my relationship bring out the best in you?”

“Are you happy and content with your life?”

“Do you wish to be raised differently?”

“Given a chance to get adopted by a billionaire would you still choose your parents?”

“Do you consider emotional cheating as wrong as physical cheating?”

“If it is not for physical intimacy, will we still be together?”

“Are you comfortable sharing your mobile/ email password with me?”

“Do you think we are soulmates?”

Related: 40 Bold Pick Up Lines To Say To A Guy To Make Him Fall 2023

“Do you consider me your best friend?”

“Tell me the story of your first love.”

I hope you have found these conversation starters with a guy helpful to keep the convo flowing and interesting to know him better.

Moreover, you can check out these icebreakers, questions to ask, nicknames for guys that are mean, funny, dirty, sexy, etc. to make a strong connection.

Related Topics:

40+ Good Pick Up Lines For Tinder That Break The Ice Every Time 2023
40+ Extremely Flirty Dares Over Text To Add Spark For Him & Her 2023
56 Epic Flirty Conversation Starters To Break The Ice & Spark a Connection 2023
Best 130+ Names Boys Like To Be Called In Relationship & When Flirting 2023