If you are like me, the thought of chatting to a guy I have never met before either via text or in person makes me cringe.
I’m sure I’m not alone.
We used to meet people in bars and clubs where the conversation flowed naturally. Now, online dating means we find ourselves texting perfect strangers from our home or meeting them in broad daylight, completely sober.
Terrifying? Yes.
Necessary if we want to date in the modern world? Also yes.
For this reason, I’ve put together some interesting questions to ask a guy. I hope they will help you to get the conversation started, get to know your potential date better, and have a bit of a laugh. They include:
- What to ask a guy in the first few conversations
- Funny questions to make him laugh
- Flirty questions to ask a guy
- Unusual questions that other people might not ask him
- Questions to ask a guy to get to know him deeper
Remember, always date safely. Be careful what you share online and for first dates, always let a friend know where you are going, who with and when you will be home.
Further reading: Red flags to look out for on a first date.
50 INTERESTING QUESTIONS TO ASK A GUY
THE VERY FIRST THINGS TO ASK
- Cool profile photos! Where did you take them?
- So you’re into (insert interest/hobby here). How did you get into it?
- How did you meet (your mutual friend)?
- Who inspired you to go into your line of work?
- I’ve never been to this neighbourhood. Could you tell me more about it?
- What places do you recommend around here?
- What’s your favourite place on earth?
- Where do you spend the most time at (besides your house/workplace)?
- Could you tell me more about your travels?
- If you could have dinner with one person, dead or alive, (besides me), who would it be and why?
FUNNY QUESTIONS TO MAKE HIM LAUGH
- If you were a cartoon character who would you be?
- Who/What is your spirit animal?
- Which do you prefer: grocery shopping or house cleaning?
- If you were for sale, how much would be the price tag?
- What’s the weirdest thing you’ve ever Googled?
- Favourite weapon for the zombie apocalypse?
- Do you believe your star sign describes you?
- What’s your funniest Halloween costume?
- Would you rather eat a caterpillar or a cockroach?
- What’s the most embarrassing thing you’ve done for love
FLIRTY QUESTIONS TO ASK A GUY
- When was your first kiss?
- Do you enjoy talking about sex?
- What does “sex” mean to you?
- When was the first time you had sex?
- Who/What is your greatest sexual fantasy?
- What’s your biggest turn on?
- What’s your favourite sex scene in a movie?
- What do you think about sex on a first date?
- What wouldn’t you do in bed?
- What is the worst/most embarrassing thing you’ve ever done to get someone in bed?
UNUSUAL QUESTIONS THAT OTHER PEOPLE MIGHT NOT ASK HIM
- Who are you planning to vote for in the next election?
- What was your life like in isolation during the pandemic?
- Were you one of the first people to get vaccinated?
- How important are holidays/religious days to you?
- Are you spiritual/Do you go to church?
- Would you date or marry someone with a different religion/political view?
- What is the most important social issue for you right now?
- How important is alone time to you?
- Would you consider yourself a neat freak?
- Who is the person/s you cannot live without?
QUESTIONS TO ASK A GUY TO GET TO KNOW HIM DEEPER
- Are you worried about the future?
- What are your plans for the next five or ten years?
- Where do you want to settle eventually?
- What do you think of marriage? What about divorce?
- Do you want to have kids of your own or adopt?
- What kind of parent do you think you would be?
- Do you like living close to your family?
- What does your dream home look like?
- What is something that you would like to get better at or improve on?
- What are your personal values?
