Earlier this year, I photographed Isaac’s surprise proposal to Kelsey. Now, both of them want to share tips on how to pull off a surprise proposal. Enjoy this guest blog post!
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Did you know 37 percent of engagements happen between November and February? Sounds like ‘Tis the season for proposals! If you’re planning to pop the question anytime soon, we’d love to share tips with you from our experience.
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- Ask the parents. Are they more traditional? If so, you may want to explicitly ask them for your partner’s hand in marriage. Couldn’t care less about tradition? It still might be good to let them know your intentions.
- Purchase the ring thoughtfully. You could get advice from someone who knows your partner or even go ring-browsing with your significant other ahead of time. If you choose the latter, know that you can still have a surprise proposal—they won’t know where, when, or how you’re going to ask! Think about what’s important to your partner: what kind of stone? Band? Is sustainability or history important to them? What’s their ring size?
- Figure out the how and when. For this, consider your significant other. Would they want their friends and/or family there? Is there a place that’s meaningful to your relationship? These were the most important factors for us. The World War II Memorial in Washington, D.C., was where we had one of our early dates, and having our best friends there was important.

How do you keep the ring hidden for weeks or months?
This one is tough, especially if you live together. (Kelsey even found a “suspicious-looking box” under the bed at one point.) Our advice would be to get the ring as close to when you’re planning to propose as possible. The less time you’re hiding or carrying it around, the safer you’ll be.
Should you hire a photographer?
YES! We both agree this was the best decision we could have made. Engagement photo shoots are always beautiful, but
our shoot with Ana felt even more special because she was able to capture us in the moment. The imperfection of it all also felt very authentic—we were laughing, crying, and soaked with rain, but the photos clearly showed our joy.
If you’re involving a photographer, book them well in advance and make sure they have experience with surprise proposals. You’ll want someone who can be covert!
Should we dress up?
This is one of the biggest risks you take with a surprise proposal. The best advice we can offer is to plan the proposal around an outing for which your partner will be dressed presentably—a nice dinner, an evening out with friends, etc.
We’re officially engaged (and we have some gorgeous photos!). What now?
Above all else, make sure the most important people in your life know you’re engaged before you publish anything online. We made sure we told our parents, grandparents, siblings, and closest friends before we posted any photos. This was nearly 24 hours after the proposal, but it was worth it.
Have any tips to add? Questions for us? Leave a comment. Otherwise—if you’re proposing—good luck!
– Kelsey & Isaac

Photo by Ana Isabel Photography