Surprise Proposal Boston Engagement Photography
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Surprise Proposal Boston Engagement Photography

Surprise Proposals Tips and Tricks: How to surprise propose to your significant other

Planning a surprise proposal is a little tricky. There are a few moving parts to think of when trying to hash out the details I have compiled our best ideas based on years of experience. First, you have to get the ring and keep it out of sight and safe from your significant other. This can be a challenge if you live together and have a CSI detective in the mix. I have had clients who have hidden the ring in plain sight and those that have stuffed it in a sock drawer. Once you have the ring you then need to start planning how to propose. You first want to pick a location.

What location should you pick?

Well, it all depends on the type of person your significant other is and the type of relationship you have. Do they like adventure, do they like romantic, do they like surprises? Are they one for public attention or are they more private? Answering these questions will help define what kind of proposal you should do. If they like adventure and its normal for you to set off on a weekend hike, or go on a trip, this might be the avenue for you. Proposing on the top of a mountain with a glorious view could cover both adventure and romance. If they like the public displays of attention and won’t be bothered by the public act, finding an outdoor water view (Like at the Seaport District on Fan Fair Park) is a great place. In Boston, there are a few areas with rooftop views of the city, that fit the bill for scenic and romantic. This photo here was taken during an engagement session at the Boston Public Garden over by the Boston Common. There are great on-street parking and a parking garage. It's within walking distance to Newbury Street (a great shopping center) and some of the best restaurants in Boston!

Here is a list of rooftop locations for proposals in Boston. This a list of hotels with views of Boston:

The Liberty Hotel

The Envoy Hotel

The Royal Sonesta

Marriott Cambridge

Revere Hotel

Few locations outside of Boston with a view of the city skyline are

Robbins Hill in Arlington

Blue Hill in Canton

The parking garage by Aquarium in downtown Boston!

The top level of the parking lot at the Science Museum

Fan Fair Park Seaport District

How do you involve the photographer when planning a proposal?

Well, this piece is a little bit trickier. It’s not impossible, but if you have a CSI detective for a significant other, it can be tricky.

There are a couple of ways to do this. First, you can arrange for the photographer to be at the location that you would like and snap photos without her noticing. We call this first method tried and true is hidden in plain sight. You let the photographer know where you would like to propose and you hash out the details of the exact spot. If you pick a busier location, they are more likely to blend in with the crowd and the photographer won’t be standing around looking like they’re waiting for you. You also want to take a selfie the day of the photoshoot and text it to the photographer if you’ve never met before you also want to text a photo of your significant other. What I normally suggest is that you take a selfie together so I can see what my couples look like and then text it to me.

The other method is to just walk up to the hired photographer and say “Hey... can you take a photo of us with my cell phone photo?” This can be used as code you are about to do it, and helps the photographer pose you. I often make a joke "Oh well, I actually know how to do this, wait... let me put you in better light..." The photographer will then pose you and you can then do your thing after you get your cell phone back. I call this the photographer distraction technique!

It's pretty easy and natural for a photographer to take the cell phone take a couple of photos then as you get out on the switch to the professional camera and get snapping. This is probably the easiest method to make sure everyone is prepared for the big moment.

You want to make sure you check out the weather a few days before the event. If you are looking to do an outdoor proposal, Snow can be really pretty and romantic but rain is not as much fun. Nobody wants to be out in the rain.

When proposing...

You are going to be nervous, you are a ball of energy, you cannot wait to get this over with and get that ring out of your pocket onto their finger!! The thing about engagement photography for me is that the session is fluid. I can’t really talk to the couple and pose them in good light, you can’t direct a couple and say "wait" and fix something.

While it is not common, you could have a situation where the photographer doesn’t get the photo. Expectations are key! If you were in a public place you are libel to get people walking through your shot. I have had situations where the location had obstacles in the way. You want to be aware of where the photographer is. I always encourage my clients to take a few minutes and talk to their significant other so that I can get a good pulse on where they’re standing at the best angle. You need to take a beat because if you don’t you’re liable to end up with not ideal photos.

If you can walk down naturally to your spot, Talk to them about how long you’ve been together and how much you’ve enjoyed everything they’ve done and talked about your favorite thing you’ve done together or talk about a place you want to travel too. Anything to kind of give your photographer just a minute to figure out where they need to be and what’s going on.

If you go right into the location and get down on one knee the photographer might not be in position, and they might actually miss it. I had a situation where the groom gave me seven seconds to take a photo and that is not a lot of time in photography I need to make sure I’m in the right spot before you do propose. Once down on one knee do you want to stay there for an extra five seconds while they register what’s happening?

You also need to decide whether or not you want to have a full-blown engagement session and or just the proposal and one or two portraits afterward.

If this is a surprise engagement proposal session you want to make sure that your significant other has on clothes they would be happy with. There are ways to convince somebody to wear something. If your significant other has long hair tell them how much you love it up and say will you wear your hair up today for me or do you know how pretty you look with your hair up.

What should we wear? How do I get my girlfriend to wear something nicer?

If your significant other doesn’t wear the right clothes or they don't have hair or makeup that they are going to be happy with, I always suggest that people hire me again to make sure their significant other has the photos they want. Sure the great moment will still be captured, they won't care what they looked like while surprised but they WILL care if they show up in sweatpants to a photoshoot of real photos of you together. In the end, these are photos they’re going to have for a long time.

They are going to love the fact that you have put in the time and effort to hire an amazing proposal photographer.

Should you hire a photographer for proposal?


What is the cost of a proposal Photographer?

The cost of proposal photography is different photographer. My cost of portrait photography runs $600 and includes one hour of time, helping to plan the session and all high resolution jpg files for printing. I also will put together a signature album for you to view and purchase

Location: Boston Public Garden 4 Charles St, Boston, MA 02108.

Reading Photographer Headshots-Portraits-Kids-Families, Senior Portraits 40 Marla Lane, Reading MA 01867 781-315-6030 -