How to Chat Up a Guy

Don’t know how to let that cute guy know you’re into him? We’ve got your back.

CLEO (Singapore) - - CONTENTS -

We get it, mak­ing the first move can be scary. But in this era where women are mak­ing things hap­pen, we shouldn’t just pas­sively sit back and wait for a date to land in our laps.

Mak­ing the first move doesn’t mean you’re throw­ing your­self at a guy; it just means you’re step­ping into your power as a woman and mak­ing de­ci­sions about what you want. We asked Kaile Chin, a re­la­tion­ship man­ager at lo­cal dat­ing agency Gai Gai, for some tips on how you can ask a guy out in dif­fer­ent sce­nar­ios.

If you matched with him on a dat­ing app…

So you’ve matched with this guy on Tin­der. Now you’re just sit­ting by your phone, wait­ing for him to say “hello” first. But what if he doesn’t make the first move and you lose out on a po­ten­tial re­la­tion­ship?

Kaile sug­gests start­ing the con­ver­sa­tion by show­ing in­ter­est in his pro­file pic­tures. If they’re travel pho­tos, ask how those ex­pe­ri­ences were. And if they’re of him, say, play­ing a par­tic­u­lar sport, ask him what he loves about it.

If he’s a col­league…

Hav­ing a crush on your co-worker can be a lit­tle dan­ger­ous be­cause things can get awk­ward if it doesn’t end well. But that be­ing said, if you gen­uinely want to get to know him bet­ter and pur­sue this of­fice ro­mance, Kaile sug­gests that you find a chance to speak to him alone, and that you “leave an air of mys­tery so you’d leave him want­ing to learn more about you”. You can also leave the of­fice at the same time as him so you’ll be­come a fa­mil­iar face, and fol­low him on In­sta­gram!

If he’s a friend…

It’s al­ways a huge risk go­ing from buds to beaus. You don’t want to lose him as friend but at the same time, you can’t help but won­der if this re­la­tion­ship could be­come some­thing re­ally great. This could go both ways, and Kaile says to start off slow and go on group dates. When you feel con­fi­dent enough, ask him out for a ca­sual din­ner date and take it from there.

If he’s a friend of a friend…

Just let your mu­tual friend know about your crush. Kaile says, “If you trust your friend enough, let them know so they can help to play Cupid and cre­ate more op­por­tu­ni­ties for you guys to hang out.”

If you just met him at a bar…

Got your eyes on this in­cred­i­bly cute guy sit­ting alone or talk­ing with his friends at the bar? Try to talk to him when he’s alone. Kaile sug­gests ask­ing ques­tions in­stead of mak­ing small talk. “You can ask him about what to drink or eat at the bar, and then try those rec­om­men­da­tions out,” she says, adding that you should “find a safe topic to dive into” be­fore ask­ing for his num­ber—if he doesn’t ask for yours first, that is!

Ini­ti­ate a con­ver­sa­tion but al­ways re­mem­ber to leave an air of mys­tery so you'd leave him want­ing to learn more about you.

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