50+ funny first date questions to ask a man to know his sense of humour

Going out for a first date as a woman can be exhilarating but overwhelming at the same time. Preparing for a date requires you to look pretty and maintain a conversation. Sometimes discussions are not easy, and this is where funny first date questions to ask a man come in handy. You do not need to be a comedian; just hilariously shoot light questions.

Getting to know your potential partner in person is essential. First dates are supposed to be fun and should take a little time. Look for funny online dating questions to ask him and make it engaging as you enjoy your day together.

Funny first date questions to ask a man

These are questions that will leave him cracking up and get him to reveal bits of his personality at the same time. The concept of a first date is to know the person better. A first date is what determines the next meet-up. This could be in the form of a second date as friends or something more. Here are funny questions to ask a guy to make him laugh:

• Have you ever been in a situation where someone called you the wrong name? How did you react to that?
• Which celebrity do you think you look like?
• Tell me one inappropriate moment that you found yourself in.
• What’s the most embarrassing thing that you think shouldn’t be embarrassing?
• Something you’re scared of that most people don’t find scary?
• What’s the most extended lie-in you’ve ever had?
• How bad is your road rage on a scale of 1-10?
• Have you ever been on the receiving end of a practical joke?
• What’s the craziest nickname someone has ever called you?
• Do you have any claims to fame?
• No falsehood; what is currently on your mind?
• Which accent do you find funny?
• Which celebrity couple can’t you stand?
• What old-school beliefs do you still hold?
• Was there anything you believed as a kid, then discovered it was a myth?
• What trend do you consider lame?
• What’s the weirdest thing you have ever done that no one would believe you did?

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• Name three of your guilty pleasures.
• What are your trash TV shows that you are addicted to?
• Who is that one actor considered problematic but still a favourite to you?
• What is the most ridiculous social media challenge you participated in?
• What genre of music do you think should not exist?
• What’s that one thing that always cracks you up?
• Do you laugh at lame jokes respectfully or find it hard to pretend?
• What was your very first kiss like?! And how old were you when it happened?
• If you were to write a letter to your younger self, what would you tell yourself?
• How nervous do you get on dates?
• Who’s your celebrity hall pass?
• Which social media platform has the fakest of all people?
• If you could dress me in anything for the rest of this date, what would you put me in?

Random fun questions to ask your date

You can be random with your questions to make it more enjoyable. Don’t be a dull date who only speaks when spoken to. Keep the conversation going even when your date seems out of stories. By having the following hilarious first date questions, you subconsciously make your date fall in love with your personality:

• What would you choose if you could have a lifetime supply of either Coke or Pepsi?
• What smell of alcohol reminds you of a bad memory? 
• What’s the most boring TV show you were forced to watch?
• Have you watched The Office? If so, which character best suits you?
• How quickly do you eat your food at home? 
• Cats or dogs for pets?
• Which entertainer do you honestly think has no natural talent?
• A weird food combination that you swear by?
• What food could you simply cannot live without?
• What was your last Google search?
• What’s the weirdest thing your siblings have ever caught you doing?
• What’s a childhood song you loved but now hate?
• What’s a childhood TV character you adored but now cannot stand?
• Are you a clumsy person? Share the clumsiest you have ever been.
• What’s the silliest thing you are known at home for?
• What subject can you give a lecture on without preparation?
• Which cartoon character looks like a family member?
• How many times do you use filters on your photos?
• Which celebrity would you punch in the face if you ever met them?
• Who would you choose if you could pick one famous person for a new best friend?

• If you were a rapper, what would your rap name be?
• What’s something you’ve tried but would never do or have again?
• Who’s that one celebrity that you used to crush on but no longer do?
• What’s the most essential thing about you?
• What’s the most cringe song you secretly love?
• Are you the chatty drunk? Oversharer or emotional drunk?
• Would you still date your high school crush today?
• What’s your go-to stress meal?
• What’s the most unhinged thing you’ve done this year?

Entertaining first-date questions

Don’t go on a date to sit in awkward silence. Instead, look for funny first-date conversation starters to entertain your date with. You can start with the following easy questions to gauge their personality, then gradually move to flirty first-date questions if the vibe is right:

• If you had to change your name, what would you change it to?
• If you got famous, what would you be famous for?
• Are you an active or inactive group chat member?
• What kind of child do your parents think you were?
• Do you believe in ghosts?
• If you were to play a movie character in real life, who would it be?
• What’s the last lie that you told?
• Would you rather aliens or robots take over the world?
• What would it be if you were dragged on Twitter for your unpopular opinion?
• What’s the most embarrassing post you have ever shared on Facebook?
• Which TV show do you think should be cancelled?
• What’s the weirdest thing you do when you’re alone?
• Do you think you’re a good liar?
• What’s one job you’re incapable of but confident you could do anyway?
• Facebook or Twitter?
• How often have you stalked your ex on social media after breaking up?
• What do you think your therapist would tell their friends about you?
• What do you think your boss tells their friends about you?
• Which would you pick if you could live in any decade other than this one?
• Were you a likeable person in high school?
• Who’s the most overrated celebrity right now?
• What’s the most ridiculous thing you’ve ever cried over?
• You have to wear one of your past Halloween costumes for the rest of your life. So which one are you picking?
• What would your presidential campaign slogan be?
• You get to switch bodies with a model for one day. Who would that be?
• What’s more fun between Instagram and Tik tok?
• Name one male and one female celebrity that you are currently obsessed with
• If you were a cocktail, what would you be?

• Would you rather be known for your pretty face or your intelligence?
• Have you ever stood up a date?
• Do you think believing in astrology is dumb?
• What is your most used emoji while sexting?
• What was your pandemic hobby? 
• Have you ever been stood up before?
• Have you ever lied when talking to a prospective partner?
• How many dating apps do you have on your phone?
• What would you instead be made public, your po*rn history or the last sexual message you sent?
• What’s something that you did to your sibling that landed them in trouble?
• What’s your honest opinion about the current regime?
• Would you rather be a bat or a snail?
• Have you ever stolen anything from your mother’s purse?

Funny first date questions to ask a man are easy if you have researched and learned a little about the person you are meeting. From the texts you exchange before the date, you can tell the kind of person they are. Make the day pleasant, fun, and delightful, and soon you will see the gent ask you on a second date.

Tuko.co.ke also published an article on answers to respond when asked, “Why do you love me”. There are so many reasons that can make your boyfriend want to know the answer. For example, he might be deeply unsure of himself or insecure about the relationship.

Always ensure your response makes him feel valued and special when asked this question. Don’t forget to use your best tone and voice to make him feel convinced.

Source: TUKO.co.ke