Hey, the places to chat up guys in the last century are pretty much the same places to chat him up now

The 40 guys we asked also let us in on the opening lines that work best.

Portrait of Tammy Strobel

The 40 guys we asked also let us in on the opening lines that work best.


Why: “A cafe is relatively peaceful and quiet, which makes it easier to chat. Plus, I’m more likely to be properly dressed and groomed!” – JL Teh, 35

Your opening line: Use the communal seating to your advantage and get a conversation going. Keep it casual; ask how his weekend is going, what’s good on the menu or which brews to have.


Why: “There’s something exciting about travelling. It’s a chance to discover new places and new people.” – Arthur Teo*, 29

Your opening line: Make small talk during the last two hours of the flight. This gives you an out in case your pickup attempt goes belly up. Target solo travellers: swop travel plans, tips, anecdotes and, if you’re lucky, phone numbers.


Why: “If I’m browsing in a certain section of the bookshop, there’s a higher chance that the person in the same aisle will potentially have similar interests.” – Andy Lim, 28

Your opening line: Pay attention to his book and kick off from there. Also, pick a genre you’re familiar with – there’s no point in pretending you’re keen on science fiction when you don’t know your Star Trek from your Star Wars.


Why: “It’s unexpected. I give the person props for being able to break an ‘awkward silence’ moment.” – Shaun Spykerman, 28

Your opening line: Chat up that guy in front of you and ask how long he’s been waiting in line, or why he’s willing to brave the queue. With nowhere else to be, he’ll be more inclined to engage.


Why: “Parks are conducive for starting a conversation. Even when I’m out on a run, I can still chat with people or comment on how cute someone’s dog is.” – Wai Kit, 38

Your opening line: Don’t fret if you’re pet-less. Park yourself on a bench and offer a smile or a friendly greeting to the next cutie you see. The casual setting (plus endorphins from his run!) means he’s likely to feel less inhibited.


Why: “Typically, there are more men than women at sporting events. It’s a pleasant surprise if a woman approaches me at a football match, and I’d find it easier to make a connection with her.” – Michael Lee*, 30

Your opening line: Ask him for the low-down on his favourite sporting heroes. It’s a foolproof way to start a conversation, and he’ll be only too happy to oblige.

*Names have been changed.

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