How to Date – An Introduction

They don’t teach you about dating, sexual intimacy and relationships in school. Most of the population is learning through trial and error,...

Written by Amy C · 4 min read >
How to Date - An Introduction - Heart Hackers Club -  - Virgin Active

They don’t teach you about dating, sexual intimacy and relationships in school. Most of the population is learning through trial and error, the media and yes, pornography. So as a columnist who studies and observes relationships, I thought it’d be helpful to share some insight on dating. Do note, I am a textbook Type A personality and am writing through that lens. You should consider the personality type of the apple of your eye when thinking about your own approach.

1. Speak your intention

Being coy and beating around the bush typically equates to lackluster results and skirting around the chance of rejection  Nothing great in life ever resulted from being passive. Good and mediocre maybe, but never great. Whether it be business or romantic relationships, great results have always began with an intention, and subsequently the investment of energy and effort required to actualize that desire into reality.

Speak your intention. Hints and  passive questions are a waste time. If you’re interested, own it. If you want friendship, state it.

2. Stop hedging and make an investment

Hedging is a strategy  where one reduce’s the potential loss on an investment by counterbalancing the loss in some way. It’s an attempt to avoid choosing only one thing, to remove chances of future disappointment, problems or making the wrong decision.  While hedging your bets is common in financial investing,  you also see the same approach occurring in dating. An example is to have tons of options around, investing 35% in person A, 15% in person B and so forth. There are back up plans for back up plans so you never really risk hurt, rejection or needing to commit because you have so many people on the go. This strategy might work if  you’re looking for unattached, uncommitted  fun. And it may be a safe way to see which one out of the myriad of options ends up taking spot #1. If that works for you, then all the more power to you.

The thing is, many keep options around for the wrong reasons, one of those being pure boredom and a need for constant attention. In addition, hedging is a strategy often used by those with people with avoidant attachment styles, because it averts intimacy. In such cases, the options are just distractions that stop you from developing true love and intimacy with someone.

If you meet someone who you feel is worth exploring potential with, then give it a try. Invest in the person. Give that relationship a real chance. It may last a month, a year or a lifetime, who knows? All that matters is when you look back in life, you know that you tried and gave it an honest shot. And that’s all we can do, try. And if it doesn’t work, then you move onward and forward.

3. Make a decision

Indecisiveness is an apathetic habit of our culture. We live in a world of infinite options and consequently a prevailing sense of “fear of missing out”. Thus, its tempting to approach life with one foot in, to revel in maybes, constantly hold out for better options, and procrastinate decision making until the last minute. But there is maturity and courage that comes from making a commitment. Commitment takes risk, and with that, the potential for reward. Commitment takes discipline. Commitment requires integrity for follow through. Perhaps its society to blame or pure laziness, but I think we could do with less maybes and benefit from adding more “yes’s” to our approach in life. Take a chance. Yes or no. In or out. Be brave enough to commit – whether that be to a person, a passion or a plan.

4. Ask someone out properly

In this age of hookup culture and “hang-outs” courtship is becoming a lost art form. If you are interested in someone, a Facebook poke or an Instagram happy face emoticon is not enough, unless you want to stay in the friendzone.

You may be afraid of rejection – but that looming fear of “what if” will hinder you from getting a date. Take a chance and ask the person out on a date. But do note – there is a way about asking. “We should hang out,” or “We should grab a coffee sometime,” is not asking someone out on a date. The ask is important because it implies intention. If you’re interested romantically, asking something along the lines of “Would you like to go for dinner next Friday? I know a great place <insert suggestion> that I’d like to take you to.” Why is this a winning ask? First, unless it’s business networking, typically people who have just met and want to only be buddies do not ask to take you out for dinner. Second, you are showing consideration by recommending a venue and third, you are being assertive in your ask and have provided a date in the near future. Overall, position the ask so it makes it easy for the person to say “yes”.

 5. Let people know where you stand

When you have a relationship with someone (whether that be casual, intimate or serious), and no longer want to continue, end it with respect. It’s the decent, adult thing to do. Avoiding the uncomfortable conversation is not dealing with it. Waiting for it to die off is not dealing with it. Not responding to the person is not dealing with it. In fact, it is mean and selfish. The hearts of others are not meant to be playthings, discarded when you’re bored or have changed your mind. Having an honest and upfront conversation with the person to let them know where you stand is a way to handle an ending with integrity and grace. Sure, the person on the receiving end may not like what they are hearing, but you can only control how you behave and how people react is their issue. At the end, you know you did right according to your values and there aren’t loose ends where people are guessing where your heart and head  is at.


Dating is fun and can be helpful in teaching us about what we want and need, and who we are compatible with. But first, it’s important to know what you want. Do you want a relationship with one person or are you looking for uncommitted fun? Be honest about what you want and also what you are ready for. And for those of you who are petrified of rejection, remember that we’re all similar in the sense that we’re all after the same thing: love and acceptance. Treat people that cross your path with respect, be honest and upfront, and be daring. Dare to express. Dare to ask. Dare to try. It may not work out with many, but all you need is one.

Photo credit: Riccardo Delfanti

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Written by Amy C
Amy Chan is the Founder of Renew Breakup Bootcamp, a retreat that takes a scientific and spiritual approach to healing the heart. Marie Claire calls her "A relationship expert whose work is like that of a scientific Carrie Bradshaw" and her company has been featured across national media including Good Morning America, Vogue, Glamour, Nightline along with the front page of The New York Times. Her book, Breakup Bootcamp - The Science of Rewiring Your Heart, published by Harper Collins, will be released Fall 2020. Profile

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