Your Guide To Asking Someone On A Date

Some say that the ancient art of in-person courting is dying a slow death at the hands of apps like Tinder.

However, there are corners of the world where dating is still practiced and a number of people around who don't want to see it die, so we may as well keep a discussion open about how this whole dating thing works, or at least, starts.

This article, conveniently broken down into three parts for your reading pleasure, will attempt to prepare you for step one of your dating journey: how to ask someone out.

Part One: Preparation.

So, you think you’d like to ask someone on a date? Maybe you’ll go to the movies; maybe you’ll have dinner; the details are up to you. But first, spare a thought for what you want out of this date and why. Are you thinking about a relationship? Are you lonely and seeking companionship? Are you just asking someone out because all your friends are coupling up? Make sure that you’re clear and happy with your reasons. Your next step is to do a brief risk assessment: what are the likely outcomes of asking someone on a date? A guide has been included to assist you.

Possible outcome 1: They say yes.

Pros: Date!

Other considerations: Where to from here? Friendship? More dates? A relationship and the ups and downs it entails? Rings???

Possible outcome 2: They say no.

Pros: Potential for dates with others ("when one door closes...").

Cons: Potential for embarrassment; it might affect future relations with this person.

Possible outcome 3: Radio silence/ vague answers.

Pros: You get to practice navigating the subtleties of human behaviour.

Cons: Potential for awkwardness; might affect future relations.

Still want to proceed with asking someone out? Read on!

Part Two: The Asking.

This has been done many different ways with varying levels of success, so I will simply list some of the tried and tested methods of those who have gone before us:

1. The “Straight Up”

Requiring a moderate to high level of confidence, you just go up to the person, look them in the eye and ask them out.

Pros: minimal preparation time, minimal execution time; you are proven to be a courageous lion of a person.

Cons: you may have to deal with face to face rejection (but life skills FTW).

2. The Classic “Would You Like To Go To ‘x’ With Me?”

Got a ball or a dance coming up? Ask your potential date along!

Pros: You can sort of hide behind the event.

Cons: Might cause some confusion about whether it’s a date or not.

3. The “Wing”

Enlist a mate to wing for you.

Pros: If it doesn’t go to plan there is a degree of separation between you and your would-be-date.

Cons: 3/10 points for bravery; potential for confusion.

4. The “Hotline Bling”

Call, Txt or MSG your date request.

Pros: It’s the safe middle ground between “The Straight Up” and “The Wing”.

Cons: Paper trail…

All of this leads to...

Part Three: The Aftermath.

So, you’ve NOW asked someone on a date. Eeeeexxhale. From here, regardless of the outcome, my advice would be to take a deep breath, relax and take things one step at a time. Rejection isn’t the end of the world; it’s an unavoidable part of it. If that’s what you got, take stock and turn your energy to other things/ people.

A positive response doesn’t mean you have to start planning the wedding. Go at your own pace and enjoy yourself. Whether you wind up dating or not, treat the other person with respect and behave in a way that makes you both feel comfortable.

There you have it: how to ask someone on a date. I have to say… I’ve never actually tried it myself. I usually just drop hints or rely on my (patient) friends’ match-making efforts instead.

However, I do have a solid 23 years of experience in people-watching, so this is all still legit. Who knows, one day I might just use my own guide? ‘til then, to all you potential daters out there, I wish you the best of luck. May you have fun with your dating and one day impart your wisdom on this ancient art on to the next generation.

Congratulations to Dominique for winning this writing challenge, answering: The Secret To Asking Someone On A Date. Dominique wins a $50 Westfield gift card for her submission. For your chance to win, check out our latest writing challenges in our Comps section. Also, be sure to follow this guide on how to win the writing challenge!

Photo: iStock