Breaking the news to someone who has been consigned to the proverbial friend zone is tricky. We’re not talking about the douchebag who has been harassing you, but the nice guy who has been a perfect gentlemen, or even the bro who has always lent a listening ear. While you appreciate him, sparks have never flown between the both of you. What should you do if he begs to differ? 

Scenario 1: He gives you flowers and asks you out.
Admit it, it’s like kicking a kitten. If you respect the friendship, he deserves you taking the time to at least seriously consider accepting the offer of a date – an immediate rejection could be a real blow to his ego and the friendship might never be the same again. But if you still can’t see it happening even after thinking it through, don’t leave him hanging – be straight up and tell him you value his friendship but you’d rather keep it platonic. Being rejected is always a bummer, so give him space and time to recover, even if it means temporarily losing your buddy for a while. Don’t be impatient – he’s only human.

Scenario 2: He drops hints and gives longing looks.
This is admittedly a tough one, and there is no right or wrong answer – you’ll have to judge the situation based on the friendship. Have there been ample opportunities and mutual trust for him to air his feelings, but he’s just too shy to make a move? If so, seize the bull by the horns and initiate the conversation. It’s the only way to get out of this grey area – unless you’re willing to wait it out (which only works if you’re casual friends) until his feelings hopefully fade. Our opinion? Better out in the open than suffer awkward conversations. When it comes to his reaction, it will correspond to how you bring up the subject. Perhaps start with a text message so he has time to think before replying. In any case, be prepared for him to get defensive. And if you’ve really misread the situation, don’t be afraid to apologise.

Image: Antonio Guillem /
Text: Cleo Chew
Additional text: Clara How