How to Plan a Proposal with an Undercover Photographer

 

Before every proposal session, I send out this list of pointers and tips to help set up my clients for the best possible photos. 

Camera in Bushes Narrow.jpg

Since the logistics and undercover nature of these sessions often calls for a bit of foliage, few people, and a scenic backdrop, we often end up at Fort Zachary Taylor State Park, so the majority of this article will pertain to that location specifically, but I also shoot proposals at the Reach Resort, Casa Marina Resort, South Beach, and Sunset Key.

And of course the majority of the advice can be used at any location, regardless of where you end up.

WHY DO I NEED TO KNOW THIS?

You might be thinking "How hard can this be?  Don't you just follow me around until the big moment and then start taking pictures?”

In a nutshell, Yes.  But Proposals are shot "incognito".  I'll be hiding and capturing the moments as they unfold.  Unlike a normal session where I can direct you and move around a lot, once this type of session gets underway, I have little control, so knowing all of this ahead of time helps us achieve the best results.

ARRIVAL TO THE PARK

ENTRY - This beach is in a State Park, and they charge a small entry fee (note - if you have a Florida State Parks annual pass, however, it is good here too!). Otherwise, have a few bucks of extra cash to get in ($4.50 - $7.50 depending on how many people are in the vehicle).

PARKING - You’ll first pass a small parking area off to the right by the fortress itself. Keep going. The next area is a big paved oval shaped lot, where cars enter to the right, and exit on the left side. This is the area you want to park.

If you reach the gravel and dirt lot, you’ve gone too far, and will waste a big chunk of your session time walking.

Fort Zach From Above.jpg
Key West Engagement with Jeep.jpg

KNOW YOUR RIDE

I will be watching the driveway and parking lot for your car to arrive, so knowing ahead of time what you will be driving is super helpful.

If you are renting a vehicle, let me know what you’ll be driving once you pick it up. If you are taking an Uber or a Taxi, you’ll need to be ready to text me once you get into the car and are en route to the location.

GETTING TO THE SPOT

Proposal-Schematic-at-Fort-Zachary-Taylor.png

Download the Fort Zach Map HERE 

When you get out of your car, go into the main walking entrance by the bathrooms and showers...it's a very obvious entry point so won't be hard to spot...it will wind around by the concession stand and tiki hut. Feel free to roam about. I'll stay just in your periphery.

Come in by the concession stand 

There's a little walkway in from the parking lot). This is where I'm going to look for you to come in. 

  
  !….READ THIS --->
Keep your phone on you!!!
<----READ THIS....!

The park is pretty big, so if something happens to where I can't find you or you don't see me, if you have your phone then we can track each other down.  If I see you come in, I will text "Got you".  If you don't see this text, assume I don't see you (and obviously, don't propose yet). :P

It’s going to come in really handy if you’re one of the people who accidentally:

  • COMES IN THE WRONG ENTRANCE

  • BRINGS A DIFFERENT CAR I WASN’T EXPECTING

  • ARRIVES AT THE WRONG TIME WHEN I’M NOT WATCHING FOR THE CAR

  • GOES INTO RESTRICTED AREAS

  • LOOKS GENERALLY LOST OR CONFUSED

In other words:

  • IT SEEMS LIKE THE ONLY TIMES SOMETHING GOES AWRY, ARE THE CLIENTS WHO LEFT THEIR PHONES BEHIND... 

WHILE I'VE NEVER MISSED THE MOMENT, IT EATS UP VALUABLE TIME (that you're paying for) AND NEARLY GIVES ME HEART FAILURE (which I have to pay for!)  LOL.  

Photo Courtesy of  Sara Kurfeß

Photo Courtesy of Sara Kurfeß

The best spot is the left side of the beach.

Guy proposing on one knee to girlfriend on Fort Zach Beach in Key West

On the map, this would actually be on the right side of the image...you enter the park toward the top right area of the photo and the entrance driveway winds around and opens up to a main parking lot). 

At that time of day, people are starting to pack up and leave so there are less people, as they're making their way to the rocks to watch sunset. So you usually end up with a big area of beach all to yourself and a background of open water and sky and it's beautiful lighting at that angle too. 

Just don't go "all" the way down the beach to the chain link fence that separates the park from the navy base, otherwise you'll have part of the fence and a big ugly satellite dish in your background because that far down it's hard for me to get in a good spot. 



You might not see me

As you're wandering about or sitting on the beach, or whatever you end up doing, I'm going to be pretending to be a tourist.

Hiding in Bushes Waiting on Key West Proposal.jpg
Couple On Park Bench Before proposing in Key West

I shoot with a long lens, so I’m often very far away but still able to zoom in very close and see the action.

I can't stare at you incessantly the entire time or she may sense it. I typically look at you, look away and shoot a flower, look back and see where you're at, and so on.

If I sense that you're unsure if I see you, I'll send a text simply with "all good".  That way if she looks at your phone, it will seem like a vague text from a number she doesn't know.  

BEST PRACTICES

The “Double-Hand-Hold” Visual Cue

So that I can see from a distance that "this is the moment", before you drop to one knee (or whatever other gesture you decide) - hold both of her hands for about 10 seconds. 

Hold Both Hands As Cue For Proposal.jpg

Feel free to talk to her while you're holding her hands. Without this, there's a chance I turn around from taking a "fake botanist documenting a flower", or stepping gingerly over a pronate sunbather, to find you already down on one knee and me scrambling to reposition myself...

I need those few seconds of warning in case someone is in my way or I need to change positions.

Positioning for best light

Position so that her left shoulder is toward the water (her face toward the sun so she is well lit).

This ensures you're parallel to the water (your right shoulder facing water), and at a good angle from my viewpoint in the tree line just next to you.

Which Direction to face when proposing for best beach lighting

Put down all the "stuff"

Woman holding lots of gadgets needs more arms

If she has a purse or bag of some kind, or has a camera strap she's holding, find a way to have her put those things down.

Cross-body straps are not flattering, and a phone in her hand is difficult if not impossible to have retouched out later.

Usually if I get the real moment with her "stuff" all on her, I will ask later if you want to recreate it without all the stuff, which is more photographically flattering of course but definitely not as genuine, so ideally we want it off before the big moment.

Have her put down:

  • phone

  • bag

  • camera

  • drink

Watch the Long Locks

Hair falling forward during Key West proposal.jpg

If your soon-to-be-fiance has long hair and wears her hair down and to her right (the side that will be facing me), when you go down on one knee, her hair is going to fall forward when she looks down toward you, blocking her face. 

If it's possible, try to put her hair behind her ear before kneeling down. If it comes up naturally in conversation and you're able to casually suggest she wear her hair back, or in a clip would work too. If you're not planning on kneeling down, then this becomes less of an issue, but in that case if she has long hair, it's nice to maybe tuck it behind her ear - that can be romantic too. :) Of course it all depends on whether you would normally do that. you don't want to make her think "what in the world are you doing?" Lol.


Channel your inner "Whack-A-Mole"

This is the visual I get when someone proposes on one knee for only a split second then immediately pops back up...nooo!  Whack!   

If you're proposing on one knee, you'll feel like you're down there for eternity, when in the real world it's been about 0.74 milliseconds.  Instead, just imagine a softly-upholstered mallet keeping you in place for an extra 5 to 10 seconds.  

Why?  This gives me time to get all her expressions while you're still "in the moment".

I'll get the shot no matter what, but I may not get the best expression of her (remember she has no idea she's being photographed, and looks of surprise and shock can come across in a photo as confusion or anger before she ultimately realizes what’s happening and smiles.. You don't want the expression of "what the heck are you doing?" on her face, so stay on one knee long enough for it to transition to the “OMG Yes!” expression you’re looking for.
 

whack a mole game.jpg

Closing Time

If you’re proposing at Fort Zachary Taylor Beach, the park's closing time is very finite and they do not permit us to keep shooting after the sun goes down...

Sunset proposal shoot.jpg

The rangers will literally drive around and kick us out, and I've even seen them drive their golf carts between a photographer and his subjects to physically force them to stop shooting when a photographer did not comply (not to mention getting a nicely-worded warning that would prevent future use of the park for photo shoots if it happens again).    

I say this only to make sure you understand that if something causes you to run late arriving, we will still get the proposal, but you may just end up with less portraits afterward, so I like to make this very clear up front as I have no control over it.  

WHAT IF I FORGET? 

It's a lot of info, and you don't have to get it all down perfectly, and no matter what happens or where you end up, I will shoot whatever happens, but this is just some extra measures to get the best possible photos, from a lighting, timing, and logistical standpoint.  Think of them more as guidelines rather than "hard and fast rules".  

Whew!  And WooHoo!

I want to set us up as much as possible for success since I can't direct you from my hiding spot.  Let me know if you have any questions on anything, and I'll see you at the shoot!