Ana and Brent

How We Met

Brent and I first met during our freshman year of high school in 2007. We tried dating a few random times from freshman year of high school to sophomore year of college, but the timing just never worked out! After we both graduated from college, I reached out to Brent because I saw that he had moved away from our Florida hometown to Los Angeles for law school! This very much intrigued me! So I initially reached out to him just as friends and we quickly started progressing; however, we were both super reluctant because we both said we wouldn’t do long distance (I was living in Florida at the time).

Marriage Proposal Ideas in New York

My beautiful sister (and maid of honor!) has lived in Melbourne, Australia for the last 8 years. My mom and I had a trip planned to go see my sister on November 10, 2015! Guess where our 8-hour layover would be?! Yup, you guessed it – Los Angeles! Wink wink! This was all such a (meant to be) coincidence! When my mom and I landed in LA, Brent picked me up from the airport and we spent the entire 8 hours together! He took me on a cute date to the Santa Monica Pier! We went on the Ferris wheel right along the water and watched the most beautiful pink and purple sunset. There we had our 2nd first kiss! We both didn’t know where this was going at the time, but we knew it felt so right!

Proposal Ideas New York

Fast forward through 2+ years of long-distance flying back and forth between LA and Florida to see each other, on January 13, 2018, I made the most exciting move of my life and moved across the country to Santa Monica, California to move in with Brent! This has been the best decision ever (minus leaving my family in Florida). If you ask anyone that knows me, they’ll say I will attempt to (and may probably convince you) to move to California! Two months into the new move, we picked up our child – Walter – the cutest Old English Sheepdog puppy in the world. (@waltersheepdog on Instagram!!) We have now been living our best life together in California for the past 2-years and wouldn’t change it for the world!

Where to Propose in New York

How They Asked

I woke up on December 21, 2019, thinking it would be another great, normal day! Brent and I flew from California to New York to spend Christmas with our families! We woke up on that Saturday with a busy, fully-planned day! Brent was being extra lovey-dovey but I didn’t think much into this – mostly just “omg he is being extra cute today!” We had been walking a lot that day, so my dad told me that his knee was starting to hurt and that he was just going to head home and rest while Brent, my mom, and I go shopping! About an hour of shopping goes by and suddenly Brent (without giving us any notice at all) calls an Uber to go back home. Mind you, Brent never makes rushed decisions like this so I found this a little weird, but again didn’t think too much into it because I was kind of tired too! My mom was being a very good actress supporting Brent in his decision to start heading home because she knew exactly what was going on – the two of them were in on it the whole time!

Wedding Proposal Ideas in New York

When we arrived back to our apartment, Brent asked if I wanted to go to our building’s rooftop quickly just to see the beautiful view – it had been a few years since we were last in NYC and we love the rooftop to our apartment. It was our first night in New York, so I said: “definitely, it will probably be so pretty right now!” So we head upstairs together and I open the door to the rooftop. The first thing I see is this cute girl with a professional camera looking at the Chrysler building with her back turned to us. This seemed fishy, but I thought to myself “well there are a lot of renters in this building, a lot of photographers in New York, and I mean it is the Chrysler building – I would probably take a picture of it too!”

Ana's Proposal in New York

Then I looked the opposite way and I saw the cutest champagne set up with some greenery and a blanket…AND a taped arrow on the ground!! (LOL) THIS was the moment I knew it was happening!! The view of the sunset was absolutely breathtaking. Brent took me to the edge of the rooftop and looked me in the eyes, said some really sweet things about all of our years together, got on his knee, and asked: “Will You Marry Me?” Of course, I said a big fat YES! It was everything I had dreamed of and more! My parents and my dog came to the rooftop and we all hugged each other!

To my even bigger surprise, I learned that my dad went home not because of his knee but to meet my 2 best friends in our lobby to let them both into the building! They decorated the rooftop and the inside of our apartment and then after a few minutes had gone by they came running up the staircase towards me and I started immediately crying on the spot! My cheeks hurt so much from smiling that day (and they hurt just as much now just thinking about it)!

Engagement Proposal Ideas in New York

It was so perfect.

Ana and Brent's Engagement in New York

Special Thanks

Kristine Kelly
 | Photographer