How to get married (my 5-step plan in finding a wife)

tim chan —  February 13, 2012 — 13 Comments

Marrying my wife Olive was one of the defining decisions I made in my twenties. This is the story of how it happened.

When I turned 23, I created a 5-year plan for my life. In year 3 I would travel for an extended time. In year 4 I would start dating someone seriously. By the end of year 5, I would be engaged. Things happened faster than I had planned. Four months before I turned 28 (the end of year 5), I was watching the beautiful Olive walk down the aisle to be married to me. This didn’t just happen. It was part of my plan. Mostly. Let me explain.

photo credit: Auzigog via photopin cc

While I was travelling around Asia at 25 years old, I knew I wanted to get married in the next 2-3 years. So I came up with a plan to get married. I had read an article challenging my view on dating and marriage. The author wrote about trusting God while taking initiative in dating. When you are looking for a job, you don’t just sit there and pray to God to provide you with a job. You actively search for a job. You write your cover letter and resume, search for job postings, apply to jobs, go to interviews, etc. And you are trusting God to provide through the entire process. But when it comes to dating and marriage, many people just sit there and wait for the perfect person to come along. Why is that?

The article challenged me to date the godliest, smartest, most beautiful and most eligible girl I knew in my life that would say yes to dating me. So I took action. I created a plan and I executed on it. My perspective shifted from waiting for the perfect girl to come along to taking the initiative to find the girl I would marry.

How? Here was my 5-step plan.
1) Make a list of the top 5 most eligible and available female friends in my life
2) Visit each of those female friends to determine who is at the top of that list
3) Reconnect with the person at the top of the list and muster up the courage to ask that person to date me
4) If the person says no, then wait a while and ask again (ask at least three times). If they still say no, then go to step 3 and repeat with the next person on the list. If the person says yes to dating, then date and together decide whether or not to get married. If we both decide not to get married, then break up and go to step 3 and repeat with the next person on the list. If we both decide to get married, go to step 5.
5) Get married

Nice and simple right? Well, as in most cases, the execution is more difficult than than planning.

Step 1. I came up with the list of the top 5 most eligible female friends in my life, people who I respected and who I could see myself potentially marrying. People who I thought were cute (a very important factor… I know, so superficial right?)

Step 2. I reconnected with each of the friends on my top 5 list. I met up with them for coffee, asked them how they were, what they were doing, where they were headed in life, etc. There were a few key things I was looking for. First, was that person mature and ready to get married in the next 2-3 years? Two of those people were happily single and didn’t even have marriage on the radar. The second thing I looked for was if the person was going anywhere in life, and if that direction matched my direction. I was looking for a person that was willing to take risks in their life; a person that had proven she was trusting God and living by faith. After reconnecting with everyone, and thinking through and praying through the list, I determined that Olive was my number 1 choice. She was a friend I really admired and respected. She was super cute. She was in her 2nd year of doing missions in Asia and had proven that she lived by faith, took big risks, and trusted God. And did I mention that she was very cute?

Step 3. Olive was in Toronto at that time, so I made up an excuse to connect with her regularly. She was reading through a book called “Spiritual Living in a Secular World” which she recommended to me. I just suggested that we read the book together and discuss it. Like a book study. Somehow she bought into the idea, so there was my excuse to talk to her every week and ask her deep questions to get to know her better. Weeks later, she happened to have a week of training in Vancouver (God was obviously helping me out with my plan). Her parents even came after her training was finished, so that their family could spend some time travelling. I generously offered to drive them around while they were here. My true motivation was not only to spend time with Olive, but also scope out her parents to make sure they were not psychotic. Because if they were the controlling, psychotic, dominating Asian parents, then maybe I wouldn’t be so interested. But they were pretty cool. So that was okay.

When I tell this story to people, they ask me what Olive’s response was, because my behaviour sure was suspicious. Olive had no clue what was happening. She’s clueless sometimes – for her own good.

The hardest part was mustering up the courage to ask her to consider dating me. I had a lot of trouble doing this. My plan was to ask in the new year (in January). Obviously God thought I was moving too slow, so He sped things up by prompting Olive to ask me “are we just friends” question in October.

The conversation went something like this:
Olive: “I want to ask you something”
Tim: “Okay”
Olive: “We’ve been spending quite a bit of time together… while we were in Vancouver and talking regularly over the phone.”
Tim: “Yeah….”
Olive: “So… where is this friendship going…?”
Tim: (silence)
Olive: (waiting)
Tim: (more silence… )
Olive: (still waiting… feeling awkward…)
Tim: (even more silence… feeling very awkward…)
Olive: (finally breaking the awkward silence) You don’t have to answer the question right now.
Tim: Okay (feeling very relieved and embarressed)… Ummm, goodbye then. (hangs up)

photo credit: bitzcelt via photopin cc

She totally caught me off guard. I did call her back the next day (she later told me that she was worrying the entire time that she had just ruined our friendship), and told her I was very interested in her, and suggested that we take the next two weeks to pray and discern whether to move forward in our relationship.

Step 4. On November 2, 2006, Olive and I decided to start dating. I made the occasion special by pre-recording a song (I re-wrote the lyrics to Diana Krall’s “Let’s Fall in Love”) and emailing it to her. I also emailed her a handwritten letter asking her to consider dating me. I read out the letter while she read along because I knew I would be very nervous, and I didn’t want her to misunderstand what I was stuttering. Her answer? “Yeah” (This is the blog post I wrote shortly after we started dating, recounting how I felt).

We defined dating as an intentional exclusive relationship that would last at most 2-3 years, and the goal of this relationship would be to find the answer to one question. That question was, “Should we get married?” If the answer is yes, then we should get engaged and married. If the answer is no, then we should break up. Very simple. Our dating relationship would be considered successful when we answer this question, no matter if it is a “yes” or a “no”. I know many people that consider breaking up to be a failure. I disagree. If you break up because you’re not meant to marry each other, then I would say that the break-up is a success. Why would you want to stay dating a person you’re not going to get married to?

I felt it was very important to have a time frame for our dating relationship, because it communicated that I intended to be very intentional. It also showed that I respected Olive’s time and my own as well. I didn’t want us to rush into a decision, but I also didn’t want to drag it out. The last thing I wanted to happen was date for 5 years and then break up. If we were going to break up, then we should do it sooner rather than later. Neither of us was getting any younger.

Step 5. After dating for 15 months, I asked Olive to marry me. I sang her a song before I proposed. She said yes. We were engaged for 7 months before getting married on Oct 11, 2008 in Toronto. I surprised her with a song during our wedding. It was a last minute decision. Now I know every time I need her to say “yes” to something important, I should sing her a song first.

Here’s the song I sang Olive at our wedding:

So there it is. My 5-step plan on getting married. And it’s by the grace of God that this plan worked for me.

(Olive’s side of the story can be found here and here.)


  • Volney Hui

    Hello Tim and Olive,
    I am very, very touched by your sincere sharing about your journey to marriage. I am very thankful that you bothered to write it down and share & teach other people your insights.
    That means a lot to me. There are not many people willing to take risk to share something like that, when there is no definite answer to how God brings 2 people together.
    May God greatly bless you and your family, because of your kindness to others.
    Thanks! Volney

    • Thanks Volney, we appreciate your comment!

  • I feel that is among the so much significant information for me. And i am glad reading your article. But wanna commentary on few normal issues, The web site style is great, the articles is truly great : D. Excellent job, cheers

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  • My fave line is ” Why would you want to stay dating a person you’re not going to get married to?” THIS IS SOOO AWESOME :D!! Sharing.

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  • Spiritual Klutz

    Wow. That was some intense decision-making. I can’t imagine what kind of discussions were required for deciding to have kids!

    • Yup! Both my wife and are think alot and love to analyze things… the process of deciding to have kids also took a while!

  • ginjx

    I loved the article and thinking of using it to encourage the guy friends around me to do so XD. I was also wondering if there is a female version from Olive on her thought process on this while being a woman in waiting? thanks!

    • olivechan

      What a great idea for another post! I definitely want to write one. Stay tuned! Thanks for the suggestion. :)