5 Steps To Making Your Marriage Proposal The Best Proposal Ever

categories: Date Idea, Romantic Ideas

Please take a moment to watch my proposal to Olga & Eva in the video above.  Olga has described the proposal as the “best proposal ever” but obviously that is a highly subjective standard. What it really means is that it was the best proposal she could have ever imagined, which is all that matters to me. Read about how learned about the secret menu! If you are planning a marriage proposal, then making it the best proposal ever in your girlfriend’s mind should be your ultimate goal too. But how do you actually go out and make that a reality? With the benefit of hindsight, I reflected on what I did right and identified 5 steps that, if followed, will put you on the path to creating the best proposal ever as well.

Step 1 – Think Long And Hard  – This is probably the most important step of all, yet most often overlooked. Keep in mind that this is a moment that your girlfriend has dreamed of all of her life. You owe it to her and to yourself to spend quality time thinking about what you can do to make it special and planning exactly how you are going to make it happen. As you can see in the video above, my proposal involved a lot of moving parts, including coordinating with the sand castle sculptor and videographer. This took careful planning and a little help from a really cool (and free) piece of software called Skitch. You can see how I used Skitch to ensure that everything went according to plan in .

Step 2 – Do Something Memorable – There is something beautiful yet simple with just getting on one knee and popping the question. But if you really want to blow her mind, then try to do something outside-of-the-box. In my case, I knew I wanted to involve Eva in the proposal as well, since this is really about the three of us starting a family together. So when I was brainstorming ideas, I tried to think of something creative that would appeal to both of them. Eva was 2 years old at the time of the proposal and in full-fledged princess obsession mode, which is what spawned the idea of having a sand castle built. If you can think of something that is not only unique, but also relevant and meaningful to your particular relationship then you have yourself a “best proposal ever” idea. If you need some inspiration, I would suggest taking a look at from the Knot with 50 unique proposal ideas.

Step 3 – Get Your Proposal On Video Or Photographed – As you can tell by this video blog, I’m a big proponent of video and photographs. I know it’s not for everyone, but unless you think your girlfriend would be uncomfortable or would want the moment to be 100% private, then I would highly recommend hiring a photographer or videographer to capture the proposal.  If you don’t want cameras right there in the open during the proposal, it is also possible to hire a photographer to take photos from a distance. I know this is an added expense, but you only propose once and Olga and I are both so happy that we’ll have the video and pictures from that day to look back on forever.

Step 4 – Have Family And/Or Friends There To Celebrate – While I would not advise you to have family and friends present during the actual proposal, I know that it meant a lot to Olga for our families to join us afterwards and celebrate the moment with us.  Unless you are planning to propose out-of-town (which is a great option), I would highly recommend that you consider inviting your family and/or closest friends to celebrate with you right after the proposal. Scope out the venue first to see if there is a private room or other place where your guests can remain hidden during the proposal itself and then appear afterwards for congratulatory hugs and kisses. It’s such a special moment in your lives, and it feels great to share it with the people who are most special to you.

Step 5 – Keep The Surprises Coming  – If you get a YES, then both you and your now fiancee will be on Cloud Nine. I knew I wouldn’t want the day to end right after the proposal, so I planned for that to be just the beginning. The rest of the day was one surprise after another. Instead of staying at home that evening, I surprised Olga by booking us a room at the SLS Hotel, a posh hotel in Beverly Hills. For dinner, I had made reservations at Mastro’s, one of the finest restaurants in the city, where we enjoyed champagne and one of the the best meals of our lives. Despite being in a food coma after dinner, I was able to convince Olga to head down the street with me for one final drink to cap off the evening at Nic’s Martini Lounge. Unbeknownst it to Olga, all of our closest friends were waiting at the bar to toast our engagement. It was so much fun seeing Olga’s jaw drop time and time again as I kept the surprises coming over the course of the day.

I hope that you enjoyed the video and find these ideas helpful.   Note that the vast majority of our content on this blog is aimed at general date ideas and romantic gestures for every day use. So please make sure to poke around our blog for ideas that are more practical for your relationship.


First and foremost, I’d like to thank Olga and Eva for saying YES. I’m so grateful to have both of you in my life, and I am so excited for the wedding in September and the wonderful years ahead.

If you are interested in having a sand castle built for your proposal (or for any other occasion), then look no further than . In particular, Greg Lebon was an absolute pleasure to work with, and I believe his skills and artistry speak for itself in the video.  Greg, thank you for making such a beautiful sand castle for us that we’ll remember forever.  Eva is still talking about it to this day, and I’m confident it is something that she will remember forever.

A special thanks to and Armando Macias for filming the proposal on short notice, and for doing such a great job on the fly. We only had 1 take for this, and you guys couldn’t have done a better job.  I’ve known Noam for many years, and he is an incredibly talented filmmaker and the director of our forthcoming Shit List series.  If you are ever looking to shoot a commercial for your company, Noam is your man.  Armando is a master sound designer.  We actually met for the first time on the proposal day, when I sprinted into the men’s bathroom to get mic’d up before the proposal.  I had told Olga that I desperately had to use the bathroom when we got there, and Armando masterfully set up the mic and tested it in a matter of minutes so I could get back outside before Olga had a chance to sense something was going on.

Also, without the patience and editing skills of , there is no way this video would have ever come together so beautifully.  Thanks you Nic for sticking with me for all those months and creating such an incredible final product.


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  • marya

    u guys are soooo cute together !!!!!!!!!

  • marya

    post more videos !!! please !

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