Things You Never Knew You Needed to Know About Proposing

Eli Holmes
5 min readMay 19, 2023

I’ve been engaged, I’ve also photographed well over 200 wedding proposals in my lifetime, and 500 weddings. Wedding proposals — these are my jam, my favorite thing, and what I most likely will make a career out of. And the biggest reason: they’re just really fun, chaotic, and very emotional.

What I’ve found having been the facilitator of so many people getting engaged is that no one ever is really prepared for what’s about to happen. Like you’re prepared for the decision. You’ve been thinking about this, you’ve probably also already talked about it. But the nutty gritty, the day of stuff — that is a whole different ball game.

Much like a wedding ceremony, there’s a lot you expect will happen that does happen, a lot you expect that won’t happen, and just a lot of unexpecteds. And honestly I’ve never heard of anyone having a fairy godparent through this process — maybe that should be my new title “Engagement Fairy Godparent,” oh what about “Engagement Facilitator,” “Facilitator of the Engaged.” So you’re just out here, wilding this engagement with the many bits of feedback, and expectations from the folks you talk to.

Well, let me give you the scoop on some of the most quirky parts of getting engaged that most of my clients don’t think about or know.

1) You will black out.

The knee drop is about to happen, and you were so solid in it all until now, and they said yes, but now what on earth did you say in that knee drop? And they’re probably wondering the same thing. The first thing I do when I leave a proposal is tell them “talk about what you just shared with each other, and leave that ring on for the morning when you can have the same conversation all over again snuggled up in bed tomorrow.”

Why do I do this? I’ll also prepare the proposer with the same advice, and remind them when I send their sneak peaks in 10–15 minutes. So this is something I remind, remind, remind for a reason. The more you say something the more your brain remembers it. This is a moment flooded with thoughts, emotions, feelings — I’m a feeling-avoidant person and had a mental breakdown in a wedding dress shop, the ones that say they’ll feel it the least, it might not go that way for y’all.

The brain remembers things the more you do or say them. And when you’re flooded with emotions and black out, you don’t always remember things, or remember them well. Having your proposer reiterate those important words once, twice, three times in 24 hours should help your brain cement those words somewhere in its tombs.

This is also a bit of why I do the ring advice — “wear your ring to bed.” When you wake up, your brain and mind are at its best and finest. Being able to sit there and go “oh right, there’s a ring on this hand now,” and quietly talk about it in bed should help your brain cement these experiences in your body. It’s a quiet, calm moment, where you’re able to process the experience with your person.

2) This is more so a show of appreciation and love to your to-be-engaged than anything else — make it personal.

Make it personal. Curate every little detail to correlate with the story of your relationship even if it’s filled with Coca Cola and McDonald French fries versus sirloin and roses. The intentional details are what really slam dunks that feeling of wow this person really cared about me and put thought into this. You don’t need 1400 roses to have a bomb or epic proposal. Backpacking in the mountains, or snuggled up in bed could be your perfect proposal if that’s personal for y’all.

The gesture isn’t the deciding factor of saying yes. It never has been in any of my experiences. Your relationship in its totality is that deciding factor, and if you’re under the age of 45 you’ve likely already had the conversation. They have already likely said yes to you in their mind before you even asked.

This moment isn’t about the yes, it’s about saying I love you and am choosing to commit to you and share a life with you. And in ways that can be even scarier. But, as someone who is F-word avoidant, you don’t necessarily have to *say* those words, you can show them. Hence why, this is about the gesture, not the ask.

3) Craft a proposal with downtime

There’s a few reasons I do this. Allowing your brain to come off the dopamine rush, and take a break gives your brain a better chance to remember every smell, feeling, thought during this experience. It’s also, honestly, just a lot. The second that news breaks, it can be a lot to manage the emotions of friends, family, and others when you’ve just had this happen seconds ago.

Give yourself downtime. When I photograph proposals I structure things perfectly for that. I am on-site for the knee drop, then I leave. The two always have chairs and beverages to relax and enjoy with. They can sit and chat and have a quiet moment before getting on their phones. Then usually it’s off to dinner and I’ll see them later that weekend for an couples session to have more formal imagery.

This allows them to experience the emotions fully and focus on the experience versus the photos in that really sacred time post knee drop. For me this is super critical. This is that time where you want folks to experience things fully, candidly, organically. I need to be a fly on that wall during this time. This is a super vulnerable experience, and introducing another personality to the mix can totally shift how people experience it with each other.

So, I shoot and dash! Well, kind of. I come ahead of time, stalk my prey, keeping enough of a distance that I just look like any other tourist bumming around a cool spot, and wait for that knee drop. I photograph it, find the right time to be like “hey! Congratulations, you’re so beautiful together, here’s a spot to relax, talk more, share more of what y’all said or wanted to say to each other, and I’ll see you later.”

Remember the black out? Well, yeah, duh, I would too. This time usually allows folks to wait on the “HEY FAM/FRIENDS GUESS WHAT” moment that releases that news into the world. Once you go public, it invites all of the world to have thoughts, feelings, and opinions — keep it sacred for a little bit for the two of you to relish in just a little longer before you invite that into your happy little bubble.

So, these are some of my best words of wisdom if you’re doing the thing I’ll help facilitate till the day I die, but maybe never have the cohones to do myself. Feel free to ask any questions in the comments or reach out elsewhere.