A couple of months ago, I was out with a good friend and fellow blogger of mine, Crystal, when I told her that I’d been asking random women out dates. The conversation went somewhat like this:

Her: You mean, you’ve been asking random girls you see on the street out?

Me: Yeah! Why?

Her: Don’t you think it’s weird? Like if someone I didn’t know just came out to me and did that, I think I’d freak out.

Me: I don’t think it’s weird. Provided of course, you’re able to handle it if she rejects you.

Her: Well, if someone I didn’t know approached me, I’d be scared. Like, I don’t know anything about you! Why would I go out with you?

Me: Okay, so how would you like to be asked out?

Her: Ideally it’d be at a familiar event, like a gathering of mutual friends. Then it’d be okay to talk and introduce ourselves, and we could add each other on Facebook. Then I’d stalk him, make sure he isn’t a creep. If he has a blog, even better. After that, then maybe we could go out on a date.

Me: That’s fine, but what about a random guy who’s never met you? Like, say for instance he saw you grocery shopping, and he thought you were really pretty and wanted to get to know you. No Facebook, no blogs. How would he meet you?

Her: *Pause* Well… I guess it just wasn’t meant to be I suppose.


The conversation gave me an idea for an article, and I considered writing a post titled, ‘X WAYS OF ASKING RANDOM KL GIRLS OUT’. I thought that maybe it was a cultural thing – that Malaysia’s high crime rate, social xenophobia and Asian upbringing or something made girls more cautious, and there were certain ways of asking them out. I mentally drafted the article, with tips like ‘be accessible online’, ‘regularly organise gatherings with friends’, and ‘clean your Facebook profile’. It seemed like a great idea at the time.

And whatever you do, don't take selfies like this.

TIP #4: And whatever you do, never ever take this selfie.

Still, something didn’t feel right about it, like the article wasn’t in the spirit of my blog somehow. It wasn’t until several months after that conversation, after I’ve ignored Crystal’s advice and continued asking random girls out and being consistently rejected that I got my answer.

‘Wait what? If you’ve been consistently rejected, then isn’t that a sign that Crystal was right?’ you ask.

She is right, if the whole idea is to simply get a date. You could pick the safe route. Get to know your friend’s friends, until you see someone you like, start going out in groups, get to know the girl and slowly build your way into asking her out alone. There’s nothing wrong with that. In fact, that’s exactly how I met my ex (although, I did also make some pretty ballsy moves which I think made the difference).

But if you don’t want to be limited in how you interact with women, if you want to face your fears and feel empowered by going after what you want unreservedly, then here’s my advice – just ask her out. It doesn’t matter that you don’t know her, it doesn’t matter if it’s going to be awkward, it doesn’t matter if she’s going to reject you. Just step into the arena, and do your best. Forget about how it’s going to turn out – you have less control over that than you think.

In my case, it used to be that when I’d notice an attractive girl I didn’t know walking down the street, or sitting idly at the climbing gym I’d get excited and start over-thinking the situation. I should go talk to her right? But shit what if I make a fool of myself? What if she thinks I’m a creep? She looks taller than me, I’d look like some fucking midget, right? What if I…

…and I would continue being at war with myself before she’d eventually leave and the opportunity was lost. I’d feel like an idiot afterwards for getting so worked up over it. There’s the crushing disappointment of not even trying, and then the emotional haunting for the rest of the day.

Eventually I got sick of that and made it a point to face my fears. If I was attracted to her, I’d force myself to approach her. I’d make my intentions clear, and not pretend like I was just trying to be friendly. It wasn’t easy, and at the time of writing, I haven’t been out on a single date with any of the girls I’ve asked. Yup, you read that right – after months and months of trying, I’m still zero for zero in the dating department. Yet, unbelievably, it doesn’t bother me. If anything, I feel more secure with myself than I have ever been.

‘But why? Shouldn’t a date record equivalent to the Brazil-Germany 2014 world cup score make you feel like shit Khairie?’ you ask again.

You know... something like this!?

You know… exactly like this!?

Yes, that’s true – if you were asking her out for her. If you approached her with the mindset that your self-worth and personal value rides on her responding positively to you, then yes, repeated rejections are going to make you feel like shit.

But if you ask her out for you, you’ll find that it doesn’t matter what her answer is. If you keep in mind that the reason you’re putting yourself forward is so you won’t have any regrets and want to further develop yourself, you won’t care about the outcome. Her reaction just isn’t as important as how you feel about yourself.

Personally for me, asking random girls out was my way of facing my own fear of rejection and being honest about what I wantI used to only be able to talk to a girl if we had a mutual acquaintance, and even then I’d be vague with my intentions and end up being just a friend. I was so invested in the outcome, that I always just did nice, ‘safe’ things for her, never being bold or taking any risks. Ironically, this is one of the most surefire ways of losing her interest.

Today, I actually enjoy asking random women out. It still takes effort to work up the courage, but once I do, it’s easy for me to say “Hey I think you’re pretty and I’d like to get to know you better.” Whatever her response is, I know I’m walking away confidently after the interaction is done.

Seriously, that’s the best part of it all. Taking a chance, and being perfectly okay with however it’ll turn out.

That’s not to say there isn’t an ugly side to this. No matter how many girls you approach, your mind will still conjure a ton of rationalisations on why you shouldn’t do it. You will occasionally crash and burn and be rejected in the harshest way possible. Sorry, that’s just part of the whole process. Sure, you’ll eventually get better at it and someday you’ll be just as suave as Don Draper from Mad Men, but you’re not going to get there without first risking a few rejections and awkward moments.

Just remember that if you judge yourself based on whether or not she accepts you, you’re asking her out for her. You’re prioritising her judgement over yours, which means that your anxiety largely comes from your own discomfort with being honest with yourself. Ask her out for you. Keep in mind that you’re doing this so you feel good about yourself. So stop over thinking things, just grow some balls and ask her out.