ATTENTION: All The Single (And Ready To Mingle) Ladies

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

Portrait of Tammy Strobel

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

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.