6 Questions to Ask Yourself when Planning a Proposal

THE 6 QUESTIONS TO ASK BEFORE YOU PROPOSE

I’ve run a great many proposal adventures and I’ve found it takes a lot of thought to create the perfect proposal. In this blog post, I’m going to ask you a set of questions that I ask my clients.

For the sake of this post, I’m going to refer to the “proposee” as your SO (Significant Other). We’re in the 21st century and that means all bets are off on who proposes to whom. Love is awesome no matter how it’s presented. Now, on to the questions:

1. DOES YOUR SO ACTUALLY WANT A PROPOSAL?

Sorry to start this off on a slightly negative note, but this one is super important. The surprise should be HOW you proposed, not THAT you proposed. I’m not saying that you should say “Hey honey, I’m going to pop the question this Friday at dinner.” But you definitely should be extremely confident that the answer will be “YES.”

Some people aren’t ready. Others never want to get married! Make sure you’ve discussed this.

2. DOES YOUR SO WANT A GRAND ROMANTIC GESTURE?

Odds are, if you’re on my site, you’re a fan of the grand gestures. Make sure your SO absolutely wants one. Wild grand gestures are fun, but can also be stressful. Some of my favorite proposals are simple and spontaneous. The proposer carries around the ring for a month, waiting for the perfect moment, and it just happens when they’re cooking dinner at home. This proposal is perfect for some people!  

That being said, some have been dreaming about this moment for years. You want to go big, and you want to make it perfect. If you know your SO wants a big gesture, let’s continue.

3. DOES YOUR SO WANT A PROFESSIONAL PHOTOGRAPHER THERE?

Yes. Yes, they do. If you’re doing a big gesture that has even a little bit of planning, go on Yelp or Google and find a well-reviewed photographer. No, do not ask your friends to take pictures. No, don’t bring in your cousin’s friend who is in photojournalism school. Find a photographer, pay them the money they’re worth, and put this precious moment in the hands of a professional. 

Years later, you will be really glad you made that decision.

CAVIAT: For all subsequent questions, an easy baseline is, “How risky is this?” Remember, your job is to create a special moment. You will be taking little risks here and there. My goal is to help you be aware of, and mitigate, risk. 

4. DOES YOUR SO WANT TO BE PROPOSED TO IN PUBLIC OR PRIVATE, OR IN BETWEEN?

Super public proposals - This is something like a televised or big sporting event. This is super risky. I tell people often: the only time you should EVER propose at a sporting event is if you both grew up huge fans of a team, met at a game, and the team is a major, major part of your relationship. If you have any doubt, don’t do a super public proposal. These are stressful enough without thousands of eyeballs on you. 

This one was in the botanical gardens in Scottsdale, AZ. We had people on either side of the path holding people up so the proposal could go smoothly.

Somewhat public proposals - This is a much better option. Think of a “medium-public” proposal as something at a botanical garden, park, beach, maybe even a restaurant. Medium public proposals can be risky too. The two biggest factors here are strangers and weather (in that order). When it comes to strangers, I recommend having friends or hired help available to run interference. (Most people are totally cool giving proposals some space. Just be friendly about it.)

Weather is a bit trickier, but at least you can see it coming. My rule: Unless it’s 100% chance that it’ll be sunny, assume it’ll rain and plan accordingly. Final note: rain isn't a bad thing. It usually clears out all the other people and makes for some incredible umbrella proposal photos. 

This proposal was in a private space rented out at the Ritz Carlton in Marina Del Rey, CA.

Private proposals - This is a proposal at home or in a reserved event space. Home is never a bad option (except you’ll need to get your SO away to give you time to prep). That being said, it’s really easy to contain and virtually risk free. You can also reach out to hotels or restaurants. This is a bit costlier than a proposal at home or in public, that being said, it’s really nice to know that someone else will do the setup for you!

When it comes down to it, I will always push for a private location for proposals.

5. DOES YOUR SO WANT FRIENDS AND FAMILY INVOLVED/AROUND?

You’ve got a few options here. So much of this hinges on how well everyone can keep a secret. So early on, bring in the friends and family to help AND keep a secret. They can bring in useful info about your SO that you don’t know. Friends can also help make sure your SO is ready. (Oftentimes, girls will schedule salon days a bit in advance to make sure nails look good, etc.). They can also help getting your SO where he/she needs to be. 

When it comes to the actual moment- The same rule applies with the public/private question: does your SO want eyeballs on them when the knee hits the ground? If no, just have your loved ones around the corner or in the other room!

One final thing with friends, and this is the big reason why people hire me: you absolutely need a friend or two available to handle somethings. Maybe you need them to run interference with a stranger walking into the photo, or maybe they need to get a bottle of water. The big thing is to have a trustworthy friend at the ready. 

6. DO YOU WANT TO BE WITH YOUR SO LEADING UP TO THE PROPOSAL, OR WOULD YOU RATHER HAVE THEM USHERED TO YOU?

Here are the two scenarios:

In the first, you and your SO are walking along the beach at sunset. You’re holding hands and maybe chatting. At the perfect moment, you get the ring out and get down on one knee. Photographer is there and photos are great. Happy ending!

Second scenario: Your SO is with a friend, walking along the beach after a day out (maybe they got their nails done and had dinner). Then your SO sees you a ways away. He/she approaches you while the friend holds back. You propose and they say yes. Great photos, happy ending!

So what’s the difference?

Mostly it’s personal preference and maybe a little risk. 

The advantage to having your SO walk up to you is this: You’ll have time with the photographer to plan the shot, draw an X on the ground, and most importantly, you won’t have to try to force small talk when your heart’s pounding out of your chest. I usually prefer this way, but you can’t go wrong with either. 

The advantage to walking up with your SO is this: You get to control the tempo and feel. Maybe you tell him/her a story as you’re walking up. Maybe you just squeeze their hand. Either way. You’ll dictate it. Just make sure you think of something to talk about ahead of time!

That’s it!

Those are the 6 big questions I like to ask all my clients who hire me to run a proposal adventure. 

For a few bonus tips, I’ll leave you with this:

• Factor in what they’re wearing. Just like nails, it might be important to give them an outfit change if they’ve been out and about all day.

• This goes double for makeup. Are they a crier? You may need to get waterproof mascara in the mix somehow.

• Surprises are great, but not ruining everything is even better. Don’t be so neurotic in the planning and the day, that you make it a poor experience. 

• Remember, nothing is perfect and that’s ok. The little hiccups make for a better story. 

• If you want to make the proposal into an entire big day, I recommend checking out the other blog posts or reach out to me!