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How to Take Chances (A Love Story)

A story about taking chances and pushing the limits of your comfort zone.

I woke up this morning feeling grateful and a bit introspective, so I’m going to share a personal story with you.

Last night, I sat on the beach with a cold beer in my hand and my new husband by my side. We laughed, we held hands, and we talked about the amazing 7 months we have ahead of us. And as the sunset, I caught myself reflecting on all the chapters of my life that have brought me to this moment.

Right now I’m living a life that my younger self could never even have imagined and I’m pretty blown away by how everything has turned out. Seriously, how did I get here?

To be honest … it’s pretty complicated! But when I look back and trace the messy web of my life, I can see the one habit that has consistently fuelled everything awesome in my life.

I know how to take chances—how to push through the fear and take a leap of faith.

I’m sharing this (and I hope it doesn’t come across as boastful) because I think that sometimes everyone needs to hear that the path you see in front of you doesn’t have to be the path you follow. It’s not always easy, but taking chances is how I’ve learned to grow and change.

The title of this post is actually a bit misleading. At the end of the day, I can’t tell you how to take chances, but I can share one of my stories and hopefully inspire you to be vulnerable, take risks and push the limit of your comfort zone—because that’s where the magic happens!

A story about following your heart + taking chances.

Lesson One: Things Don’t Have to Last Forever To Be Meaningful

This is a love story. One week ago I married my best friend and my soul mate.

But I’m going to start with something not so romantic: this is my second marriage. And can I be honest? Even though divorce is ‘common’ these days, writing those words is uncomfortable.

The short version of a long story that I won’t be sharing is that my first marriage was to someone who wasn’t meant for me. I don’t regret getting married and I don’t feel it was a mistake, but it still stings a bit when I talk about it.

I’ve travelled the world alone and I’ve gotten myself into some pretty sticky situations, but still—leaving my marriage was the scariest thing I’ve ever done in my life. Before I got married I had a fairly blasé attitude about divorce, but once I was looking down the barrel I honestly could not imagine how I could make it to the other side. I was horribly afraid of letting everyone down.

Which brings me to the first lesson in taking chances: when you take a risk and it doesn’t work out the world doesn’t end. It was scary and painful and my life felt upside down for a while, but at the end of the day I walked away a bit wiser and a bit more worldly.

Our ‘failures’ (and I use that word loosely) are our biggest teachers.

H2: Lesson Two: Being Vulnerable is Better Than Living With Regret

I met my Englishman (the man I married last Friday) in a backpacker’s hostel, half a world away from home. We were staying in the same dorm room.

I was travelling through Europe alone and, although I travelled alone a lot when I was younger, I was feeling uncomfortable. At 31, I felt old and out of place. My first night in the hostel I was too shy to talk to anyone and I spent the evening with my book for company.

The second night, some friendly folks invited me to play a game of cards. A few beers and a few hours later I found myself laughing hilariously with a charming Englishman by my side.

The next few days were beautiful and I had a typical holiday romance; we held hands and kissed in alleyways and talked late into the night.

Then all holiday romances come to an end, right? The day came and he had a flight booked back to London and I had a train to catch.

But instead, he taught me something about taking chances. Instead of boarding his flight, he caught the train with me.

And we rode into the sunset and lived happily ever after …

Not quite! He joined me on my travels and we spent a few more beautiful, utterly romantic days together, but we were only delaying the inevitable. Soon it was time to say goodbye. (Damn you reality.)

He flew to London and I flew to the States, to stay with my mum and to try to figure out what on earth I was doing. At this stage, the only thing I knew for sure was that I was head over heels in love with a man I had known for precisely eight days.

Every reasonable bone in my body knew I was being foolish. I had just ended a long term relationship, I was flat broke and staying with my mum. To further complicate things, I knew I really needed to get back to Australia (I’m American but I’ve been living in Australia since my early twenties). I had a mortgage, a car loan, and an adult life waiting for me to come home and sort out.

A serious relationship, with a man I barely knew, who lived an ocean away (adding a third continent to my mixed up life), was the last thing I needed.

Or so I told myself … but the truth is I was afraid— afraid of being vulnerable, of getting hurt, of looking ridiculously stupid, and of all the hard work that would surely come with pursuing this relationship.

But here comes the next lesson about taking chances: ask yourself “What is the worst that can happen?” I was risking pride, ego, time, effort and money … but I’ve been embarrassed, I’ve been tired and I’ve been poor. It’s not fun, but it’s nothing I can’t live with or overcome.

But what I can’t live with, what I can’t face, and what I fear most is regret.

Within the month we both booked flights to see each other again.

Lesson Three: Don’t Settle + Fight For Your Dreams

We were apart for four months and then spent five weeks together, hopping between the US and UK. And then, having spent less than 2 months actually together, we made an elaborate plan.

For the next eight months, we travelled between the UK and Southeast Asia. I maxed out my credit cards and drained my savings. We did everything we could to stay together until the timing was right and I brought my Englishman back to Australia.

And two years after that, last Friday, we got married.

How to Take Chances - Wedding Pic

Now I have a partner (in every sense of the word) who shares my values, my hopes and my dreams.

(Remember that wisdom I talked about learning from my first marriage? The best relationship advice I can offer is to find someone whose core values are in line with yours.)

And that is my love story, one of the many chapters that have brought me to this point in my life! I hope you’ve enjoyed my story and I hope you remember to listen to your heart, take your own chances, and never settle for anything less than a life you love.

What chances have you taken (or would you like to take) in love + life? Let me know in the comments! x

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21 thoughts on “How to Take Chances (A Love Story)”

  1. Hi Jennifer,

    I first heard your story being read in a podcast recently and then I stumbled across the actual post.

    I loved your story it give me faith but I still find it difficult to calm myself down and get rid of the fear. I was wondering if you have any advice? (Hoping you can see this comment)

    Long story short- I live in melbourne (originally from auckland nz) and met a guy whilst in melbourne but he lives in auckland (originally from melbourne). We both came into this thinking it was only going to be short and sweet. But i changed my mind because i really enjoyed it and he made me feel in a way I’ve never felt before with any guy. Just like your story, it has to end right? We dated for about a month and he had to go back to Auckland. I told him how I felt but of course why would any man want to be in a long distance relationship especially when you don’t know each other for long? So we agreed to keep in touch and hopefully meet up when i go home in about 3 months (I’m going home for a while)

    However this is where i get frustrated. Until then I want to keep talking to him but also gets scared that he doesn’t want to or that he’ll meet someone else soon. I wanted to take a leap of faith but my fear is stopping me from doing so and i find it extremely hard to express myself even as a friend to him. Everyone is telling me to move on but a apart of me doesn’t want to and want to see how things turn out in the end. He’s been really responsive but as a girl I also hope he would initiate more.

    What is your advice? How did you overcome your fear? Any specific tips you could share with me? I’m really trying hard to just focus on the present but its so hard to not think about the future.

  2. Hi Jennifer,

    I originally came to your blog because of your tips on minimalism… Then I was led to this post.

    I can’t describe to you how useful this particular piece was to me.

    I JUST met someone, and have a lot of racing thoughts sooo similar to what you described in this story.

    I’m American, he’s Italian… I’ve lived in Italy in the past but I met him here, in my very own state of Colorado.

    He lives, works, and studies in the U.K.

    I’m not done with my undergraduate degree until next December, and he is going back to Bristol in exactly one week.

    I’ve known him for three short months, but I have this serious feeling of contentment with him, and I feel like I can’t let him go.

    To keep the story to a minimum, he actually is coming back to the U.S. for a full-time post doc. position at CU Boulder. But not till April of next year.

    After reading this, I feel like I can do it.

    I feel like I can actually make this work with him, and I know he is going to try, too.

    Thank you SO much for this.


    • Hi Leah! Aww, thank you so much for sharing your story with me 🙂 My best advice is if it’s something you want to pursue, then go for it. Give it your best shot even if it means putting yourself out there. Long distance/international relationships are tough – they don’t always work out – but I think the worst feeling ever is “what if”. If it works, it’s wonderful, and if it doesn’t … well, at least no regrets. Good luck xx Jen PS: it’s really cheesy, but when we were long distance we used this app and really liked it https://couple.me 🙂

      • Thank you for your response! I will surely be trying out that app with my boy. 🙂

        I really believe in the power of now, so when I have to wait for something, I have a really hard time being patient.

        I’ve tried long distance in the past and it hasn’t worked out, but I’m sure I can take on what I’ve learned from that into this new relationship.

        What do you find worked best for your relationship when you two were long distance? I know you talked about some of that in this article, but any other tips?

        Thanks again,


        • Hi Leah – I sooooo understand about being patient!! I’m a very impulsive person and not very good at waiting at all.

          As far as advice, I know this isn’t always feasible, but definitely try your best to see each other if you can. I know this might seem obvious – but sacrifice whatever you can to make the travel work. I know there are some super cheap flights between the US and UK now so if you can manage a visit, do it.

          Other than that … just a lot of the boring stuff. Treat it like a regular relationship, talk whenever you can, make plans …

          Best of luck xxx


          • Jennifer,

            Thank you for the advice!

            Certainly it would be best if I could travel to see him. This is somewhat difficult for me, because I go to school full time and work, but I can see what you’re saying about making sacrifices. I know I can continue to cut back on spending money, and eventually I’ll be able to afford a trip there.



  3. Oh my gosh, I loved reading this story, Jennifer! Such a lovely and amazing story. It’s so funny when people come into your life when you least expect them to. I’m so happy for you that your story has such a wonderful ending! And you’re exactly right that you need to ask yourself, what’s the worst that can happen when taking chances. When we were talking about leaving the US to travel, we thought of the absolutely WORST case scenario, and decided that if it really happened, we could live with that. 🙂

    • Hi Joella, thanks so much for your kind story! I was very nervous sharing the story of my divorce, but I think it was the right time to share 🙂

      Where did you meet your husband? And I’ve just had a look at your blog, it’s gorgeous. I’ve definitely added it to my reading list!

  4. What a lovely story, Jennifer! I’m so glad for you. 🙂 I was just talking with a good friend yesterday who was scared about admitting to a failure this week, and I remember talking with him about how it wasn’t the end of the world. I’ll tell him to check out your post. Have a great trip!

  5. Thank you for sharing this story with us, Jennifer! I love your attitude about taking chances – what’s the worse that could happen? I always try to use that thinking when analyzing whether or not to do something, especially if it’s something out of my comfort zone.
    Congratulations on your wedding and many happy travels!

  6. Jennifer, what a great story and congratulations! I, too, am on my second marriage. The first was short and rocky. Even though we knew we weren’t right for each other, the hardest part was admitting that to family and friends and initially feeling shame for letting people down. I know it was the best choice and eventually led to where I am today. Like you said, I’d never want to live with any regrets. I hope you both enjoy what should be an amazing trip!

    • Thanks for your comment and sharing a bit of your story too! You know, before I got married the first time, I was confident I could walk away if it didn’t work out, but in reality it’s so much more complicated. It sounds like you have made the right choice too. All the best!

  7. This story is so amazing, Jennifer — thank you for sharing it! And congratulations again!
    I think the biggest chance I’ve taken is probably when I moved to China as a directionless 25-year-old and stayed there for ten months teaching English. It’s interesting to me to think back on it, now that I’m blogging about being financially conscious…There are a lot of other decisions in my life that I look back on and think, yeah, that was not a great financial choice; I shouldn’t have done that. However, moving to China is an exception: even though I definitely lost money overall through that experience, I don’t regret it one bit. I wouldn’t give up the memories of that trip for any amount of money. 🙂

    • Sarah – you’ve got to write a post about your experience teaching! I want to hear more about it!! I taught for a summer in a small village outside Shanghai, but we were on a exchange type program and pretty sheltered.

      I know what you mean about finances … there are a lot of decisions that I’ve made that I’ve regretted as a ‘waste of money’ but travel has never been one of them.


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