Once you're engaged, everyone will be asking "How did he ask!?" A lot of people get caught up in the majesty of having an epic story to tell, but honestly that facade can be a bunch of BS.
I've photographed dozens of proposals, and the VERY BEST ONES were intimate and honest to the relationship of my clients.
The best example of a crazy proposal story is actually the most extravagant one I *almost* photographed. I was hired by the groom-to-be who went to every length to have the most spectacular story. He flew in his girlfriends family to be witnesses. He purchased us all tickets to meet at the Top of the Empire State Building (!!!!). He arranged a fancy breakfast, paired with loads of expensive alcohol just before the two of them left to meet us. I awaited their arrival with her family. For HOURS. We circled the observation deck dozens and dozens of time expecting them to show at any second. Cut to me waiting for them an hour past when I was supposed to be wrapped, and it turns out he got SO nervous that he was sick from the alcohol and threw up all over the sidewalk in front of the Empire State Building. The family kept apologizing, and I know he was too embarrassed to reach out to me again after that.
Don't be that guy.
Be THIS guy. Taylor emailed me a few weeks before his trip to New York with his gorgeous girlfriend, Madison. They were planning a trip to the city, and he wanted to make it a memorable one. He asked me for suggestions of where to get some icon shots of the skyline, and I told him Gantry Park in Queens is beautiful -- and it is! It's quiet, mostly filled with local moms pushing strollers but the park is wrapped in panoramic city views.
Taylor and Madison were just walking around the park, when they found a random girl on the bench and asked her to take their picture. The random girl was me, and he hired me to play along, and eventually catch him dropping to his knee and asking her to marry him. She was completely oblivious. It was a quiet, intimate moment that was so special to them.
As if that wasn't enough, Taylor invited Madison's Dad, step mom, and baby sister to be there to share in their joy! ANOTHER amazing surprise. Family is very important to them both, and being able to share the event with each other (and Dad's entire Facebook following) was the cherry on top. I love this so much because she called her dad right away, and he came sprinting from a few yards away! She was SHOCKED! I was in love!
The last few minutes of the session I toured the new fiances around the Long Island City Park to capture a few more moments of happiness.
So guys (and gals), a few helpful pointers while you're devising your proposal plan:
1) Do let your families know before hand!
2) Decide if you want it to be a private moment, or shared with family.
3). If you want the best of both worlds - hire a photographer to document the moment privately but can also can share it later.
4) Discreetly encourage her to get her nails done. Maybe send her on a spa day with her BFF as a gift on her birthday or Valentine's Day --just be sure to pop the questions within 2-3 days!
5) Be sure to tailor your proposal story so it mirrors your relationship. Are you normally extravagant? More low key? Intimate? Always surrounded by swarms of friends and family? Use these thoughts as key indicators while you're planning.
6) Don't let the "story" get in the way of the actual proposal. (Don't be the guy who throws up all over the place after being so nervous from trying to impress everyone).
Happy Proposal Planning! And if you're looking for a photographer to help capture and plan the moment with you -- contact me at firstname.lastname@example.org.