How To Date Like A Pro

How To Date Like A Pro

 by Yumay Chang

My single friends often ask, “How can I find time to date when I am so busy?”


You can, and it’s easier than you think.


I speak from experience.


In my 40s, I found myself suddenly single.


At the time, I was managing a sales engineering team that spanned several continents. On top of this, I had to deal with an unethical, incompetent manager. Life was stressful, to say the least.


Despite the hectic work situation, I made time for dating because being happily married is one of my life goals. I promised myself that no matter what, I would go on at least one date a week.


That year, I met the man that I would later marry.


According to the Harvard Happiness Study that spans almost 80 years, close relationships, more than money or fame, are what keep people happy throughout their lives.


Marital satisfaction, in particular, has a protective effect on mental health.

If a great relationship is what you want, but you’re strapped on time, efficiency in dating is key.


Here’s how in simple steps.


The One List That Rules Them All 


The first mistake people make is not knowing what qualities they are looking for in a partner. As a result, they are easily distracted by shiny objects.

Later, they realize that their partner lacks several vital qualities, so they try to change their partner.

“If you don’t know where you are going, any road will get you there.” ― Lewis Carroll

Trying to change others rarely goes well.


Instead, before we start dating, create a “love list.” Jot down all the qualities that matter to us in a partner, and decisively cut candidates that do not

meet this bar.


For more on creating a love list, see tip #8 in “How to Heal a Broken Heart.

It's A Numbers Game


Dating is a numbers game. We have to plan on kissing a few frogs before finding our dream partner, and this takes time. If you want to be with someone that’s 1 in a million awesome, you’ll have to take the time to sift through a lot of people.

“There is no one busy in this world; it’s always about priorities. You will always find time for the things you feel important.” ― Nishan Panwar

Sitting at home, expecting magic to happen, is not going to work.

We have to be out there and meet people.


A rule of thumb is to set up at least one date per week. Schedule it like we would a work meeting.


It is on us to make time for what is important.

Have We Heard Their Voice?


People waste a lot of time texting potential dates. Especially when the connection started online, it is easy to fall into the chasm of endless texting.

But texting marathons do not a relationship make.

“You text him, he doesn’t text back. He was obviously so excited you texted him that he fainted” ― Anonymous

If we sense potential in a candidate, step it up and ask them to get on a call.


Do this sooner rather than later.


An additional benefit of taking this step is that it weeds out dilly-dalliers that are on dating sites to burn time. These folks will bow out at this point.

Don’t Meet A Stranger


In hiring, recruiters always screen job candidates before bringing them onsite.


So why would we meet a stranger before speaking with them first?

Going on dates takes time and energy. We have to work out the logistics, dress up, commute over, and then there’s the date itself. That’s at least a few hours gone.


Since our time is precious, always screen a candidate before agreeing to meet. A phone call works, but a video conference is even better.


In communications, words account for only 7% of the information conveyed, while the tone of voice and body language make up the rest.

Unlike text, a phone or video conference conversation happens in real-time.


A candidate cannot pause to ponder what they want to say or ask friends for advice.


We get a much better sense of who the person is.


This step alone can save us countless hours.

Opt For Coffee (And Not Just Because Of The Caffeine)


Since time is a premium when you need to meet lots of people, start with coffee dates instead of lunch or dinner.


Coffee dates are ideal because they can be brief, but if things are going well, either party can suggest lunch or dinner afterward.

“Good communication is just as stimulating as black coffee, and just as hard to sleep after” – Anne Morrow Lindbergh

Another great first date idea is to do an activity that both parties enjoy.


Examples are going for a walk or a tennis game. Sports give us insights into a person’s personality, whether they are a good gauge of their abilities, and how well they handle losses.


Even if there is no mutual romantic interest, we got a workout in and just might get a sports buddy out of the endeavor too.

Get These Questions Out Of The Way First


When most people date, they chitchat in the beginning, careful to avoid anything sensitive. It is not until later in the relationship that they bring up important topics like religion, marriage, kids, and money.


This is a mistake.


In the very early stages of a relationship, neither party is emotionally invested in the relationship, so questions are not personal. If we ask a date if they want to have kids someday, it is only a general question about their attitudes towards kids.


This same question, asked a year later, would be quite personal. By then, it would be about whether they want to have kids with us.


Imagine how disappointing it would be only to find out then that our partner does not want what we want.


Save the heartbreak, and ask these questions early, preferably on the first or second date.


How we ask these questions matters. We have to come from a place of

curiosity, seeking to understand our date’s point of view.


Don’t make it about us, and do not judge their answers.


"Do you see yourself having kids one day?" versus "Do you see yourself having kids with me?" The former is casual, seeking to understand what they want in life. The latter is making it about us, and a little too much, too soon. Early in the relationship, you simply don't know enough about this person and neither do that about you to make this call. 

“Be curious, not judgmental.” ― Walt Whitman

What we want is information to help us make the best decision possible. No matter what our date’s answer is, thank them for sharing.


Per the golden rule, we should also be honest and disclose facts about ourselves that the other person needs to make an informed decision.


We live in an abundant universe; if our date’s goal and ours do not match, let them go, so we make space for someone that’s a better fit for us.


And make sure you do so in a classy way. Don't ghost them, or hem and haw when they ask you for a second date. Saying something along the lines of, "I enjoyed our time together, but I don't think we're looking for the same thing," or "I think you're a great person, but I just don't sense the connection to take this further," should suffice. 

If the person does not take your no for an answer, run. Boundaries irk abusive people, and more reasons for you to stand firm on the no.

The One Secret To Snagging The Best Partner

People who end up with the best partners are not better looking, smarter, or wealthier than the average person. They are the ones that keep their bar high and only accept the best.

“In life, you don’t get what you deserve; you get what you believe, plan, and expect.” ― Bill Bartmann

They enjoy their own company, so they are only willing to give up singlehood for someone that can take their life to the next level. They always take red flags seriously.


In essence, they love themselves.


Loving oneself is the foundation to kicking ass in dating.


To learn more about how to improve in this area, check out my article, “This Is The First Step Towards Self-Love.”

Putting It All Together


To date like a pro, we must know our value and be decisive in saying goodbye to candidates that aren’t a fit.


It is good to fail fast. Failing fast saves time.


When we come across people that behave poorly, don’t take it personally. Say, “Next!”


What others say or do is about them, not us. Be grateful that we saw the signs early so we can move on to something better.


The more people we meet, the clearer we are about the qualities we want in a partner, so update the love list accordingly. We want to “kaizen” the heck out of dating by continuously improving our approach.


Above all, love ourselves. When we love ourselves, we automatically know the right thing to do.


If you would like me to expand on this topic, or have other questions, please put them in the comments. I often write articles based on reader questions.

Happy dating!

Share this post: 
Yumay Chang

My name is Yumay Chang, and I run Life Is Love School, a global support group for childhood trauma survivors. I had a challenging childhood, and I know what it’s like to feel not good enough and not lovable. I learned through over two decades of research and plenty of trial and error how to heal so I can live a life of joy, love, and purpose. Now I help women that are successful at work but are unfulfilled in their personal lives do the same so they can also shine their brightest.


Are you ready to break free from the past to experience more love? Whether you want to learn how to love yourself or strengthen relationships with people you care about, you can benefit immensely from the advice and support in my women-only membership program.


  1. Join Life Is Love School Facebook group.
  2. Sign up for the newsletter for self-love wisdom.
  3. If you’re ready to break free of the past to experience more love, join our women-only membership program for NEW DIGITAL LESSONS MONTHLY + LIVE Q&A + camaraderie from a tribe of like-minded women, and more!



Get the latest scoop in your inbox!


© Copyrights by Life Is Love School. All Rights Reserved.