You’ve matched with a cute guy. Now what? These seven questions get you straight to the heart of who he is.

Portrait of Tammy Strobel
You’ve matched with a cute guy. Now what? These seven questions get you straight to the heart of who he is.

What’s one book that changed your life? 

Ask it because: What he reads literally speaks volumes about his outlook in life. 

“Successful people tend to be well-read,” says Violet Lim, CEO of Lunchclick and co-founder of dating agency Lunch Actually. “Finding out what he reads, and how often he reads, can point to whether this man is looking towards self-improvement.” It’s a good way to find out if he has an ambitious streak. 


Which artiste in your playlist would you love to see live? 

Ask it because: His answers will give you some headway into understanding what makes him tick, says Claire Certain, head of global trends and events for dating app Happn. How does the music make him feel? Why does he enjoy the genre? He throws up the name of an obscure band? Don’t fret. There’s no shame in admitting you’re clueless. See it as a chance to find out why this artiste gets his vote. Besides, his answers just beg for a follow-up, and that means you can prolong the conversation. 


If money was no object, what’s one adventure you’d like to embark on this year? 

Ask it because: He can get creative with his answers, which will hint at his imagination and sense of humour. “His answer will lay out his expectations, dreams and interests – all of which is useful information, to help you decide how compatible you might be, and how far this could go,” says Claire. (Read: He might be a thrill seeker whose idea of a good time is skydiving, while yours might be just dinner and a movie.) Claire says he’s also likely to return the question. A good conversation starter. 


What gets you revving to go to work in the morning?

Ask it because: What he finds gratifying about his job gives you a peek into who he is. “You’re taking an interest in what matters to him – without coming across as too intrusive,” says Claire. 

For example, he tells you his colleagues get him through the day. You know you’re dealing with a highly social person. If he finds his demanding job tremendously satisfying, he’s unlikely to give up when things gets tough. 


Say you have only $10 left in the bank. What would you spend it on?

Ask it because: This is a fun way to discover what someone’s idea of a must-have treat is. A quick poll of the Her World team yielded a mixed bag – bath bombs, coffee and Calbee potato chips (yes, really). “Because $10 is not a lot of money, you’ll be able to find out what this person really considers a necessity. That might also tell you more about his values than you realise,” says Sammi Chiang, Paktor Group’s dating and image consultant. 


Would you rather be stranded alone on an island, or with someone who gets on your nerves? 

Ask it because: It’s a not-so-obvious way to find out if he’s fiercely independent or emotionally needy. Tom Hanks’ character struck up an unlikely friendship with Wilson the volleyball after being stranded on an uninhabited island in the film Cast Away, but would Mr Potential Love Interest be okay in his own company? 

“Some people just cannot bear the idea of being alone, and would choose to spend time with someone they dislike, just to full a void,” says Sammi. He’ll also reveal what personality traits he finds unbearable – you’ll get two answers for the price of one. 


How close are you to your family? 

Ask it because: “What’s his tone and attitude when he speaks about his mum, grandma or sisters?” says Violet. What he says shows you how he treats women.