How He Proposed

Proposal Story-10

Proposal Night Outfit Deets

Alison: Lush Tunic (only $27) // AG Black Skinny Jeans // Valentino Rockstud Dupes // Black Leather Moto Jacket // Tiffany Studs // Burberry Watch // Tory Burch Boots (you’ll read about these in the text)

Brian: Black Peacoat // Ralph Lauren Jeans // Ralph Lauren Dress Shirt // Ralph Lauren Sweater // Wingtips

Happiest Thursday to y’all! Today I’m sharing something a little new with you. The Dating Diaries is taking a little break but will resume soon. (peep the previous Dating Diaries here) Why you ask??? Welp, B and I getting excited to celebrate our first wedding anniversary in October and I wanted to share some of the things we did while planning our big day! I have a bunch of fun posts to share with all of you brides to be!! Today, I thought I would get a little more personal with y’all and share our proposal story! So away we go!!!

If you read Monday’s post, y’all already know what a “Secret Date” is. If you don’t, read it here, first so you know how our proposal unfolded.

It was November and it was B’s turn to plan a secret date. Little did I know that I was going to be a fiance by the end of that weekend! So, in true B fashion…he pulled out all the stops. (I mean I know I’m a little biased, but B is THE BEST at planning dates!) Anywhoooooo, he had me talk at half day of work that Friday and we headed off. Once we arrived at the train station, I had a sneaking suspicion that we were heading to NYC. I was getting super pumped for a trip to NYC, because I just LOVE it sooooooo much. My suspicions were right and we arrived in NYC just a short train ride later. We checked into our beautiful hotel where B had reserved a gorgeous rooftop suite for us! B informed me that we were going to spend the rest of the evening looking at the Christmas displays, seeing the tree being put up in Rockefeller center and sipping some cocktails. It was the perfect Friday evening!! I honestly didn’t think anything was up bc every year since we have met, we have visited NYC to see the xmas lights and tree!

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Saturday we headed out early to the Meatpacking District. Brian took me to do a few of my fave things….brunch, wine, and shopping!! We strolled around and enjoyed the beautiful fall day! (PS: He really threw me off by buying me Tory Burch boots a few hours before he proposed! My friends back home were watching my Facebook/texts and when the saw he bought me the boots…they were all mad bc they thought he wouldn’t propose bc he was buying me expensive boot! lol…that B is quite the trickster!!)

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After taking in the sights, we headed back to our hotel to shower up and get ready for the night. We got all fancied up and headed out. We ended up at a hotel where B said we were going for a happy hour event. It was a little before 5 pm and unfortunately the event wasn’t ready to start yet. Little did I know, but that “event” would change my life forever. Since we couldn’t get in yet, we headed to a nearby bar to grab a drink.

Finally, we made our way back to the event and we headed in the elevator up to the rooftop. When the doors opened and I turned the corner, there was a little table and chairs set up with candles and champagne. I kind of started to wonder why we were the only ones were there…but I still had no idea what was coming. B took my hand and started his little heartfelt speech and got down on one knee. I of course, screamed, “YES”…I’m sure everyone in NYC heard me!!! Even more amazing….once I turned around I saw the photographer!! B had not only rented out the whole rooftop bar for us, but he had also hired a photographer to capture the wholeeeee thing!! So awesome!! We popped some champagne and the photographer took many photos of us to capture our special memory. After the photos, B had planned for everything and we had an extra 45 mins on the rooftop so that I could call everyone and tell them we were engaged!! It was such a magical memory!!

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The night didn’t end there though. B had reservations at a gorgeous steakhouse and then dessert at a fancy chocolate place!! It was one of the best night of our lives!! We rode the train home that Sunday and stopped for lunch where both of our families were waiting to congratulate us and celebrate!!!

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All in all….my hubs did such a stellar job with the proposal. I am sooooooo lucky to have such an incredible guy who goes the extra extra mile to make me one happy, happy girl!!!

Come on and share the LOVE!! How did your hubs propose??? I’d love to hear about your happy ending. Drop me a comment below!!

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Alison Dragun
Alison Dragun


  1. Julie Minear
    August 10, 2017 / 3:17 pm

    My hubby had been carrying my ring around with him for a few days. We were going to listen to a local band over the weekend, and he knew one of the guys in the band. He was going to have me called up on stage, where when of the band members was going to say he found my drivers license. Then my hubby was going to propose on stage in front of everyone. However, a couple days before, he dropped the box when he came in the door. That night I found it, and asked what was in the box. I kind of knew, but wasn’t completely sure. He proposed on the spot. But, he did have good intentions. The guy from the band even asked to see my ring that weekend, and told me that they were disappointed that they couldn’t be part of it. I was still on cloud nine, so I was fine the way it happened. Btw… my husband’s name is Brian too. True story! And, I love the way your hubby proposed. Thanks for sharing it with us!

    • August 11, 2017 / 4:48 pm

      Awwww..thanks for sharing Julie!! That is so cool that yours hubs is Brian too!! I know, my B, said he was sweating bullets trying to keep the ring a secret. It must be sooooo nerve wracking for guys to have all that pressure!! Hope your weekend is starting off well…cheers to Friday!! xoxo

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