How to get him to ask you out

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It’s been a week since he swiped right on you and he still hasn’t asked you out. What gives? We asked real women how they got him to pop the question and gathered some of their most useful suggestions for you.

1. Send lots of food emojis

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Some girls will drop hints by listing all the restaurants they’ve been meaning to try. Kelly* likes to do something a little more cryptic. Tap into the abundant resource that is your emoji keyboard. She says, “Whenever the conversation is dying, just send a single coffee cup, pizza or even a watermelon emoji and let his curiosity do the rest.”

Warning: Eggplant emojis not advisable.

2. Say no to texting

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Rui Ling* loves her daily ongoing Whatsapp and Telegram conversations with her friends, but will tell men she hates it.

“Right from the start, I tell them that I much prefer speaking face-to-face,” she says. “Once we start sharing about more personal things, I make it clear that I’d prefer to take the conversation offline.” Show him that if he wants to pursue you, he’ll have to do more than send you stickers on Facebook Messenger.

3. Challenge his tastes

If you really do end up talking about food, then you’re in luck! Most Singaporean guys are so defensive about their food preferences, all you need to do is “trigger” them. “If you say you don’t believe their favourite prawn mee stall is that great, they’ll practically drag you there just to prove you wrong,” asserts Gloria*. Best make sure you end up liking the food though, or this might become a real problem for the two of you if you start seeing each other seriously.

Pro tip: This works particularly well if he’s an Eastie. Just express doubt in the quality of beloved food places in Katong or Bedok.

4. Or exploit his competitive nature

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We all hate to lose. This boy is no exception. 

“You can bait him into meeting you by declaring that you’re sure you’d beat him in a game that you’re good at,” says Maryanne*, whose dart skills are ace. The guy she used this on ended up asking her out over and over again under the guise of wanting a “rematch”. The best part is, you don’t even have to actually be great - if he wins, he’ll get an ego boost and feel even better about the date.

5. Let him know about all the things you plan to do on your own

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“I would never explicitly tell him that I’m super free this Saturday because I’m afraid it might look like I’m desperate or don’t have friends,” admits Francine*. Don’t sweat it. 

Besides, the weekend is always much too short for the whole laundry list of stuff you want to do, like check out that contemporary art exhibit, drop by the bookstore and swing by the pet store to grab treats for your pup. The bottom line is you’re an independent girl with places to be and things to do… All you need to say is that he’s welcome to tag along if he wants, whatevz.

6. Call him out for being a pen pal

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Tess* was so exasperated by a guy on Tinder who’d been chatting with her for over a month but refused to make a move.

“He’d begin to tell a story and then halfway say he’ll tell me all about it when we meet IRL. This happened more than once and I got a little fed up because it just felt like empty words,” she says. “Eventually, I adopted a passive-aggressive strategy. I told him he could just text me the story in full, since we might as well be pen pals.” Thankfully, he got the hint.

7. Pay attention to what he says

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“Guys drop hints too,” says Alicia*.

If you notice that the man you’re chatting with is dropping hints about his lack of weekend plans, talking about that new movie he’s been dying to see, or just using any of the tips we discussed above, it’s likely that he’s just too shy to ask you out directly and is working very hard to get YOU to ask him out.

Help him out, make a casual date suggestion according to his hints and see what happens.

READ MORE: 10 dating lessons from Singapore's top love guru

8. Give him confidence that you’ll say yes

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Maybe he isn’t shy and he’s just afraid of rejection. “Avoid saying discouraging things like how all your dates on this dating app turned out terribly,” warns Yoona*. 

You have every right to hold high expectations of him, but he doesn’t have to know that before you meet. Don’t be dismissive or curt. It sounds obvious, but many of us do this subconsciously to prevent ourselves from getting our hopes up.

9. Beware of cushioning

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Unfortunately, you probably aren’t the only girl he’s talking to. “When he texts you flirty messages frequently but never makes concrete plans, you know something’s up,” Janine* notes. “Another red flag is if he only asks to meet spontaneously. It probably means someone else cancelled on him and you’re his backup plan.”

If he’s just using you as dating insurance, drop him like a hot potato.

10. And if all else fails…

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Sometimes, there’s really no need to overthink it.

Nadine* says, “If I want to meet him and he’s taking too long to make it happen, I literally text him: ‘ASK ME OUT’ and wait for response. It hasn’t failed me yet.”

*Names have been changed.