Welcome back! Last week, we talked all about how to pick the right engagement ring. Today, we’re going to answer another important question when it comes to planning a surprise engagement. “When should I propose?!” This week, we’re really getting into the nitty-gritty of how to plan your day around a proposal, and really make it special! Trust us, you’ll be nervous enough when the moment comes. The more you can plan out in advance, the more you can focus on your partner!

 

 

“When should I propose?” Choosing the right day

No matter what day you choose to get engaged, the day that you propose to your partner will be a day you both remember for the rest of your lives.

 

For some of you, the choice will be obvious. You’ll be on vacation next month with family, and know that it would mean a lot to have them gathered around in that special moment. Or maybe you’re huge fans of a sports team or a certain Broadway musical, and you’ve got tickets for the big game or show. Or maybe there’s a big transition day approaching, like a graduation or moving into a new city, and you want to put a ring on her finger as a promise that you’re in it for the long-run, even as you transition into a new season of life.

 

But for others, there’s no perfect day approaching. This means the question, “when should I propose” truly has no right answer. And this is also great! As in all things, keep your partner and the context of your relationship in mind. Do your best to choose a day that will have meaning. Is there a dating anniversary approaching? Is her birthday or Christmas Eve around the corner? If all else fails, secretly take a look at your calendars and just pick a day that works well for you both!

 

 

How to plan the day of the proposal

When Sarah and I help our clients plan their proposals, we always recommend the same thing: aim for “golden hour”. This is true at the beach, in the city, or in the mountains! If “golden hour” is a new concept to you, it’s the 60-90 minutes before sunset. During this window, natural light is most soft, most golden, and most dreamy. Golden hour is, without a doubt, the best time to take photos each day! Because of that, we recommend that our clients plan to propose ~75 minutes before sunset. Here are 3 reasons why:

1. 1. Sunset makes everything more romantic. Your partner and all their friends/family will swoon as the story is retold again and again. “It was so romantic! We walked along the beach as the sun was setting, and Cameron proposed!!” Cue tears of joy. Cue fist-bump from your future father-in-law.
   2. Sunset allows for beautiful photos. Photos of the proposal and any portraits afterwards will be better at sunset. Our clients knows that we include a 30-minute portrait mini-session to capture the excitement, love and joy that always follows a proposal. If we’ve timed the proposal for just before sunset, this mini-session captures you two in the best light!
   3. Now that your portrait mini-session is done, it’s dinner time! Let the surprises keep rolling as you finish up your mini-session and reveal that — not only did you plan the entire proposal — you also got reservations at one of your city’s nicest restaurants! Or maybe it’s where you went on your first date. Or maybe just a great taco place up the street. Either way, the photos are done, and it’s time to go enjoy your first meal as an engaged couple! Talk about your future together, now that it’s official!

 

 

Bonus Tip: How to get your partner to dress up for a surprise proposal

This is frequently a dilemma for our clients as they plan a surprise proposal. They know that their partner wants to look nice for the proposal, and for the photoshoot that follows. This is especially true since the photos will be splashed all over social media in a matter of hours! If they knew about the proposal in advance, you can bet that hair, makeup, nails and outfit would all be meticulously selected, and they’d be looking their best. But how can you achieve that same look if you want the proposal to truly be a surprise.

 

We’ve found that the best way to encourage dressing up without giving away the surprise is to let your partner know that you’re going to take them out on a nice date later that evening. This way, you can both (very naturally) get all dressed up, and it can also prime the evening for a bit of romance!

 

You can also recruit a friend or two to subtly and gently encourage a manicure or glow-up in the day or two leading up to the proposal. Just be careful with this if you want the proposal to be a surprise! This can be a dead giveaway if done without subtlety!

 

 

When the question “When should I propose?” has a part 2!

While this isn’t always possible and isn’t for every couple, we know from experience that a surprise party after a proposal can really blow the top off an already incredible night. The night I proposed to Sarah, we went out to a nice dinner after the proposal. Naturally, Sarah assumed that our nice meal was the end to an already incredible evening.

 

To her surprise, I pulled into the driveway of my college house, and our lawn was packed! My seven housemates and all of her closest friends had teamed up to help me pull off the most amazing surprise party ever! We had close to 100 people packed into our tiny living room and front yard, and it was the perfect cherry on top of the day.

 

However, we were in college, and Sarah had just moved from another city. So it was easy to plan the party without her finding out. Maybe an intimate dinner with a few close friends is more up your ally. Or maybe just having both your immediate families meet you at the tasting room of the vineyard would be the perfect surprise. Either way, think about how you can make this day totally over-the-top. Really shower your partner in all the love as your first official step towards your marriage!

 

 

In the next section, Sarah will take over the blog series and talk directly to anyone who is wondering if/when their partner is going to propose. But until then, happy planning!

 

—

 

Check out the rest of the series at the links below!

• How to Propose Part 1: “Should I get engaged?”
• How to Propose Part 2: How to pick the right engagement ring
• How to Propose Part 3: “When should I propose?”
• How to Propose Part 4: “When will he propose?”
• How to Propose Part 5: Where to propose (in Charlottesville)
• How to Propose Part 6: How to Propose to Your Girlfriend/Partner
• How to Propose Part 7: How to Plan a Proposal Weekend in Charlottesville

 

—

 

If you want to learn more about our full-service proposal planning and photography services, click here!