how to ask a girl out on a dating app

When I was on dating apps, I experienced the whole range of guys’ texting and date-asking styles. Some guys went straight from the customary “hi” to “I don’t like texting / wasting time, shall we meet f2f?”. One guy I texted for weeks and he never once asked me out even though he had a really easy opportunity - a common sport. (On hindsight, I should’ve stopped wasting my time earlier.)

The biggest questions are probably when to ask her out, and how. Let’s break it down.

first things first:

The biggest mistake isn't asking too early.

It's asking like you've copied and pasted the same message to twenty different women - "Wanna grab coffee sometime?" / “Would you like to have lunch this weekend?”

Technically, there's nothing wrong with it. But imagine you've spent three days talking about dogs, travelling to Japan and her obsession with peanut butter cookies...and then you ignore all of that and send the most generic ask possible.

I mean sure, she may not say no, but there are better ways to ask her in a way that makes her actually want to go out with you.

The invitation isn't the important bit - how you use the conversation before it is.

remember: there isn’t a “magic number” of days before you ask

One of the most common questions I hear as a dating coach in Singapore is “When should I ask her out?”

Is it 3 days, 5 days, or is it a number of messages? Surely there isn’t a correct answer - simply because everyone, and every couple, is different. The frequency with which everyone texts is different, and so is the depth of conversation before that.

With that, what I suggest is to ask yourself:

has the conversation become comfortable enough that meeting feels like the natural next step?

If yes, go for it!

If not, text her a little more. Use your gut!

(That being said, I personally didn’t enjoy texting for too long before going out with someone, just because there’s just so much pressure, so much “will they / won’t they”. To me, it also felt that after a certain age, I didn’t want to waste time texting for an uncertain amount of time before getting asked out. I would personally give a week as a maximum but this varies from person to person.)

Note to the guys who think that asking a girl out immediately is not wasting time - she doesn’t know enough about you to know what she’s saying yes to. She has no sense of your personality beyond your profile, how you speak, or how you think. That texting “buffer”, if you will, gives both of you a chance to decide whether it’s worth investing a couple hours meeting in personn.

Consider the perspective that going out with someone she hasn’t been able to get a feel of is a personal safety risk as well.

ok, we’ve texted for a while. how do i ask her out then?

This one is actually surprisingly easy - she’s probably given you the answer over the conversation already. The key is to use what she’s already told you, whether in her dating profile, at your mixer event, or over your conversation.

E.g. if she’s mentioned that she likes matcha - ask her if she has a favourite matcha place and if she’d like to go together over the weekend.

If she’s said that she feels like she needs to get out of the house, think of a walking trail that you both might enjoy.

→ Read: Non-boring, non-awkward first date ideas in Singapore for some ideas!

If she’s mentioned that she enjoys museums, ask her what type of museum (art / natural history / etc.) and ask if she’d like to go together!

The point isn’t to create the world’s most memorable first date - it’s just to show that you’ve listened, so that she feels seen.

for coffee meets bagel users only:

CMB recently launched CMB 2.0, with a Real Dates feature that was designed to target just this. The idea is that based on whatever you’ve talked about, CMB will surface both of your dating-style preferences, which you can use to plan your dates and give her options! (Girls love options)

remember:

There is no perfect script, there is no perfect way to ask. Every conversation is different and every woman is different. Trying to use a script to ask someone out is, ironically, detrimental to your chances, because it makes you sound less like yourself.

If you’ve paid attention to her, responded thoughtfully and been genuinely interested in her and what she’s shared, asking her out shouldn’t feel like a huge jump for the both of you - it should feel like an easy next step.

→ Read: A Dating Coach’s Take on The Best Questions to Ask on a First Date that Aren’t About Work

If you’re struggling with worries on how she might respond, or a fear of rejection, you are not alone. Book a free Dating Deep Dive get-to-know-you call to learn how Wan Ting can work with you to unpack what you’re feeling, what you want to feel instead, and real, actionable steps you can take to get there.

about the author

I'm Wan Ting, founder of portmanteau, a dating coach for men in Singapore.

I help good men like you stop guessing and build practical dating skills for serious relationships.