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  • Jenny and Joe Mackey

Top 5 Surprise Proposal Questions

man proposing to his girlfriend at Jenny Lake

The top 5 questions we receive for surprise proposal planning

  1. Timing?

  2. How do we not give it away?

  3. What should we wear?

  4. Do you have recommendations for dinner?

  5. Will it be crowded?

woman reacting to her boyfriend's surprise proposal


  If you’re reading this, you’ve probably already booked us for your surprise proposal in here in Jackson Hole!  With that in mind, I’m going to write this like I’m talking to you (yes you!) to help answer those burning questions that will undoubtedly arise as the days go by and you get closer to the big moment!  Proposals are by far our favorite thing to capture and with that, we’re always aiming to make the experience as seamless as possible for our clients and take the guess work out of the process so you can head into your proposal fully confident with your plan.  Throughout the years and countless surprise proposal sessions, we have found the following 5 questions are by far the ones receive most often!


Again, you’ve likely already booked and scheduled your surprise proposal session if you’re reading this blog, and you’ve likely already scheduled your session at a time that works best for you and your itinerary.  The specific question(s) we usually get are as follows:

The short answer to both of these is no.   

The long answer is below...

We’re big on client education so we’re always happy to explain the why behind the timing.  For sunrise, we recommend starting at the 15 minutes before scheduled sunrise that day.  For sunset sessions (depending on if you’ve booked a 30 minute or 60 minute session) we usually schedule you the last 20-50 minutes before scheduled sunset.  Though the sunrise light and sunset light differ (more on that here), we schedule it at those times as this is the window of when you are going to get the best soft lighting for your portraits. With Jackson being so far west into in the Mountain timezone, we find people usually aren’t used to how early sunrise is and how late sun sets.  For sunrise that can be as early as 5:30am and sunset as late at 9:08pm.  Factoring in the previous math and knowing that those are the best windows for great lighting for your session, it’s easy to see why we start so early or so late for most locations.

Bonus Question - Is the lighting really that important?  Yes, If you desire photos that have the look like the vast majority of our portfolio for proposals, then timing for lighting is everything.

How do you blend in and not give it away?

Camo.  Just kidding.  Kinda.  Our approach is simple here.  We blend in, in plain sight.  If you’ve never been to the area, something you’ll notice fast during peak season, it’s not uncommon for just about every other tourist to have a camera in their hands, or a tripod set up waiting on wild life or just capturing the famous landscapes this area is known for.  We dress very casual, usually set up a tripod or two, and voila.  We look like every other person you’ll see in the Grand Teton National Park or Yellowstone.  Funny enough, most of the time the person getting proposed to afterwards tells us they had no idea and that they felt bad as they thought they were getting in the way of our landscape shots.

man proposing to his girlfriend at mormon row

What should we wear?

The vast majority of our couples are usually what we call dressy casual.  This works well because it fits the vibe of being in a national park and not so formal that it wouldn’t give it away necessarily.  A couple of tips here, if you’re disguising your surprise proposal with a hike somewhere, this allows you to go more causal.  We get a fair amount of couples who look like they dressed for a hike.  Or, ‘hiking chic’ as we like to call it if you get a cute hiking outfit from REI.  If you’re planning on trying to get them to dress up, try to schedule a nice dinner reservation either before or after so dressing up won’t give it away.  Lastly, like we said, the majority of our couples usually go with something casual so don’t stress too much about outfits.  Always a good idea to wear something you are comfortable in and make sure you’re dressing for the same occasion.

Do you have recommendations for dinner?

Absolutely.  The Jackson Hole area is definitely a small town but plenty big on flavor and amazing culinary options for any palate.  For a list of great options, click here!

man proposing to his girlfriend in the snow at Jenny Lake

Will it be crowded?

If you’re proposing at a popular spot in the area, especially downtown or in GTNP, you can almost always count on it being a little crowded.  Now, that doesn’t mean there aren’t some spots with a little less foot traffic than others.  There definitely are a few and when that is your biggest priority for your proposal, let us know and we can help you pick a spot and time that is less likely to be busy so you can enjoy the moment to yourselves (hopefully)!

newly engaged couple popping a bottle of champagne

woman showing off her engagement ring

If we didn’t cover one of the questions you had above, never hesitate to reach out and let us know what’s on your mind!  It’s always our goal that this moment goes as close to perfect for you as we can get!

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