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July 15, 2013 | by  | in Opinion | [ssba]

Fixing Your Life (Because Ours Are Written Off)

Hi guise,

I’m really into this guy at my hostel, but being a girl i thought it was normal to wait for him to ask me out. I’m on holiday now, and i’ve decided that when we get back to uni I want to ask him out instead. Got any tips? Will he freak out? How do I do this?

Jess Cantwait



Hey Jess,

Look, I’m a straight male, so it’s hard for me to guess what it feels like to ask out a guy as a woman. In an ideal world, it wouldn’t be all that different, but sadly we live in a world which is still shuffling out from wildly different gender expectations. So instead, I’ll talk about the likely male reactions to your Big Question. Actually, no, that’s marriage. Medium Question.

I won’t mince words here: there are some guys out there who won’t be comfortable with being ‘asked out’ by a girl at all. Maybe it’s shyness, or maybe it’s because they are intimidated by strong women (read: not worth the effort). It shouldn’t have to be said that if someone turns you down because of the way you approached them, maybe you aren’t that compatible long-term.

So plan for the former, but don’t assume that’s the case. Either way, you should follow the general guidelines of ‘asking someone out’, which are usually only learned by trying and failing far too many times–hopefully this will save you some heartbreak. Note: these aren’t just for hetero women, but apply to everyone. No doubt there are exceptions, but nothing’s perfect.

First of all, think about how you’re going to do it, but not too much. Location-wise, a public forum in front of all of your friends is probably a bad idea. Nobody, guy or girl, really wants to be put on the spot like that. In terms of your phrasing, avoid the long-winded rom-com speech. Those are really hard to respond to without a team of hack writers. Definitely don’t just say “hey, I like you, so, uh… do what you want with that.” Consider what you would say in response–it’s always better to ask them a simple yes or no question like “do you want to go to Fidel’s for pizza tomorrow night, as a date?” Finally, if they say no, don’t talk shit about them to anyone, ever, because frankly you’re better than that.

About the ‘no’: sometimes it’s going to happen. It sucks, but it’s better to hear it than to pretend it was just a miscommunication. We’ve all had that person who didn’t just straight-out say ‘no’ to us (if you haven’t, you will), and it still hurts. So take the hint when they keep saying they don’t want to go on a date with you.

It’s common Wellington parlance that ‘shall we get a coffee?’ means ‘shall we see each other romantically in social situations?’, but your ask-ee might not be aware of that, particularly if they’re on the inexperienced side or you’ve got a history of friendship. It can be very useful to make it clear.

You should also think about the current relationship between you and your squeeze-to-be. If you’ve only met once or twice, the presumption of a romantic date is pretty obvious. If you’ve been hooking up at flat parties for six weeks, again, it should be pretty straightforward. That’s the best time to play the ‘coffee?’ card. If you’re friends already, you’re pretty much going to have to use the ‘D’ word, or better yet bring up your wide-eyed affection over the dinner table itself.

My best advice? Do it now. Get it over with. Yes or no, it’s better for you in the long term to tear that band-aid off now and save yourself the agony of going to town alone every weekend on the off-chance you bump into them. Chances are, everyone already knows how you feel, and the longer you wait, the less likely it is you’ll get a yes.

Then again, you could just do it the Kiwi way and go for a drunken pash. Nice.

Yours in romance forevah,



The waiting game is boring. It is excellent that you’ve decided to act. I reckon you should do it some other way than getting drunk and leaning in. I keep saying this to people, but they keep doing it, and it keeps leaving them in functional and fulfilling relationships. Maybe my current ‘offer-someone-a-rational-explanation-of-why-they-ought-to-date-me’ technique is a mistake. I don’t know.

I was having trouble responding to your situation. I racked my brain and remembered that I used to get asked out. It was fun. I liked it. (I am going to bury in this aside my general affliction of not liking anyone that shows the slightest interest in me.) To be honest, I think more guidance is needed in terms of how to play the outing. QUICKFIRE: If they order a long black instead of their usual mocha, they’re into you. If they pay $200 for dinner and you don’t even pash them, that is possibly a little mean—although I maintain my conversation is worth $100/hr, and I did not ask for the oysters. Don’t mention that you love bacon until you are sure they are not a principled vegetarian. Shame is not a date movie, and will cement any pre-existing halfhearted fear of the ssssnake. (Remember me telling you I used to go on dates?)

Ideally you’ll just get this person alone when you get back and be like “Hey, how was your holiday? Did you finally do all your washing/sort out that crazy high-school ex-girlfriend/get told heaps that you’ve changed? Do you want to get a coffee/drink/crocodile-bike with me sometime?” I don’t really know how else to do it. Hopefully they say yes. If they say no, they’re BLOODY CRAZY (that was me being your mates) but they’re within their rights.

Look, Hector is very good at advice, and has nailed this. He is absolutely correct to tell you that everyone most likely already knows how you feel, and it’ll be worse if you continue to stoke your hopes without testing the waters. (Or two other more compatible metaphors). I really can’t add anything. I’ve been re-listening to Adele, so I’m pretty fucking surprised I wrote anything positive at all.

Anchors away!


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