Pretty Much The Most Perfect Day Ever: Our Engagement
Photo by Crystal Bos Photography

Photo by Crystal Bos Photography

(Warning: This is going to be a lengthy post, but I don’t want to leave a thing out!)

Every year around Christmas time, Jimmy and I go to St. Augustine for a Christmas date night. We get dressed up, listen to Christmas music on the drive, go to a nice dinner, go on the Holly Jolly Trolley Tour to see all of the beautiful lights, and wrap up the evening with a drink at our favorite local pub. This weekend was the only weekend of the month that we didn’t have any plans, so a few weeks ago J told me to leave Saturday, Dec. 21 open to continue our date night tradition. Okay, done.

It wasn’t until earlier this week that I started seeing the signs. But then again, I also thought I was reading too much into things and hoping too much, so I didn’t really question anything. Things like:

  • Monday night, we were sitting on the couch and I complained that my fingernail broke. He immediately responded with, “Oh no! Why don’t you go get fake ones on?” In the 4+ years we’ve been together I have never had fake nails. Hmmm.
  • Thursday, I was out running around finishing up my Christmas shopping and I received this memo on my phone:
    How sweet! At first, I didn’t really think much of it because I was complaining about not having anything festive to wear on our date or on Christmas Eve, so I figured he just wanted me to be able to look nice without ripping apart my closet and being crabby because I didn’t like anything I put on. (Smart man, right?) Or because anyone who knows Jimmy at all knows just how big of a Christmas dork he is. Okay, so he wanted me to be festive. Again, didn’t want to read too much into it.
  • Twice last week he reminded me not to invite any friends on our date night. We always have parties, events and celebrations to go to and we both enjoy being around our friends, so we rarely get to go on a just-the-two-of-us date night. I never mentioned inviting friends, but he wanted to make sure I didn’t. Yes, sir!
  • Friday night, my girlfriend Sarah asked if I wanted to go get a manicure with her Saturday morning. I didn’t really want to spend $30 on my nails right before Christmas when I can paint them myself, but Jimmy insisted that I go since I rarely spoil myself like that. He suggested I get a sparkly red for the holidays (which I did.) THANK YOU for making me go, J!

So yeah, a few strange hints here and there, but I brushed them off. After all, we’ve been together for four years and four months, and I thought he was going to pop the question on every trip we went on and on every holiday that we spent together. But I knew he’d do it when he was ready, and I wasn’t in a hurry.

We got ready and headed out around 5:15 p.m. so we could be there by 6. I SnapChatted this selfie with the caption “Annual Christmas date night!” and I’m glad I did … because my hair definitely didn’t stay curled and my eye makeup definitely didn’t stay on much longer!
photo 1
We wanted to eat at Harry’s, which has our favorite outside courtyard, and we knew it would be packed … but thought 6:00 would be early enough to avoid the crowds. Well, maybe it was, but after sitting in traffic that turned our 32-minute trip into an hour-and-40-minute trip and Harry’s had a two-hour wait time, we had to revert to plan B. Which we came up with on the spot. A1A Ale Works with no wait it is! We got right in and sat right down. Jimmy kept looking at his watch and I could tell he was worried about time, but I thought he was going to surprise me with a tour or carriage ride (I’ve always wanted to do one of those.)
I enjoyed a beer and a delicious dinner of shrimp & grits …
photo 3
And Jimmy had a blackened mahi sandwich. And nervously ripped apart his beer coaster.
photo 1(2)

And we enjoyed a nice, quick dinner.
photo 2
But don’t worry – we had time for one more beer. I think he needed it to calm his nerves! Oh, and all throughout dinner he was texting, holding his phone to the side so I couldn’t see it. I figured he was texting our horse-drawn carriage driver.

After dinner, we walked into the main plaza to take pictures in front of the Christmas tree and gazebo (like we do every year.) First stop: tree picture.
Next stop: lights in the background.
Third stop: gazebo picture.

There were other couples and families in the gazebo taking pictures as well, so we found a nice spot off to the side to take pictures. I handed Jimmy my camera to take the picture (he has longer arms) and he just looked at it. Then he said, “No, actually, I’m not going to take a picture.” Then he took my purse from my hands and set them down. I was starting to catch on. He looked at me and said, “I actually brought you up here for something else.” I think that’s when I let out my first scream and said, “Oh my gosh. Are you about to do what I think you’re about to do?” He reached into his pocket, got down on one knee, and then I screamed again. And I think I may have jumped. I honestly can’t tell you what all he said … the only thing I can remember him saying is, “I f***ing love you.” Really? Dropping the F-bomb in your proposal? Only Jimmy. And it was hilariously and adorably perfect.

Then I notice people all around taking pictures and clapping. I heard one girl say, “OMG look, he’s proposing! Take a picture!” I don’t even remember saying “yes,” but everyone around heard it so I must have. I was so nervous, excited, happy and every other emotion you can think of in that moment. Then, after what seemed like eternity, he stood up, I cried, he put the ring on my finger, and I got my bright red lipstick all over him! Dozens of strangers clapped and cheered, and it was perfect. Just after, a trolley full of people came by and yelled “Merry Christmas!” and cheered. I thought it was for us, but it was just one of their regular stops. But I’ll pretend it was perfectly timed for us!

He turned me to the side and tells me to smile for this lovely young lady with a nice camera taking pictures. I did, and planned to ask her to email me the photos she took. Until Jimmy informs me that he’d hired her (Crystal of Crystal Bos Photography, who was suggested to him by the woman he bought my ring from), to capture our entire engagement! WHAT? Seriously? I am marrying the most amazing man ever. He told me that I’m always the one taking pictures and capturing everyone else’s memories, so someone needed to do the same for me. Goodness I love him.

And she did! I’ve only seen a few pictures so far, but in the few I’ve seen, Crystal captured every moment I could have wanted.

… Oh wait … sorry … got distracted by the sparkles on my left hand. Back to the story …

The RING! I was so nervous/excited/flustered that I forgot to even look at it. Though I’m not sure how I could have missed it. It’s absolutely breathtaking!!!!!! Baby did good.

We took a few more pictures at “our spot” in the gazebo, then walked around downtown for a mini photo shoot. I must say, I’ve never been the focus of a photo shoot and I didn’t know what to do! Everyone was staring and we were the center of attention. So weird, but a lot of fun! And Crystal was amazing and made us both feel really comfortable, which was extremely helpful.


Another beautiful photo by Crystal Bos Photography

Once the photo session was over, Jimmy suggested we go grab a drink at a cute martini bar up the street to celebrate.
photo 2(1)

When we got to the front, the hostess asked if we had reservations. Jimmy mouthed something to her, and she said, “Oh! You’re with the Blakeley party! Everyone is in the back room, go on in.” Way to ruin Jimmy’s surprise! We walked in and Jimmy had arranged for many of our wonderful friends to come out and celebrate with us. Meaning all of these people were able to keep this a secret!! They all cheered when we walked in, and had champagne waiting.

Jimmy made a nice toast thanking our friends for coming out and to me for agreeing to be his bride, and the rest of the night was spent celebrating.

Turns out that boy really does listen to me when I’m blabbing. Over the years, I’ve randomly said things like, “When you do pop the question, please make sure my nails are done … I’m dressed nice … we get a picture or two of the moment.” And he did them ALL, and all on his own! He even had the ring designed from scratch and custom-made so it could have all of the features I’ve pointed out over the years.

OH WAIT! I almost forgot the most important part! He called my dad a few days earlier to ask for his blessing before asking me to marry him!! My dad is the most important man in my life, and for Jimmy to have the respect to talk to him first means so much to me. My dad and his dad are the only other people who knew what was happening! Sneaky, sneaky boys.

It was the most incredible and amazing night of my life, and I wouldn’t have changed a thing (other than my shoes and bringing a hair brush!) Jimmy was so sweet, so cute and so thoughtful in everything he did, and the whole thing reminded me just how lucky I really am. He didn’t even care that his lips and cheeks were stained red by the end of the night! I love this guy with all of my heart and am so blessed to have him by my side. I can’t wait for this next chapter of our lives, and to spend the rest of my life with my soul mate and best friend. Christmas season with Jimmy is always the best time of the year, and now it’s going to be even better than I could have imagined. Especially since we’ll get to spend our first Christmas together!

Today has been full of butterflies, many smiles, and calls/texts/Tweets/Facebook posts from friends and family, and we are both so happy to share this time with all of you. A HUGE “thank you” to everyone who helped Jimmy pull this off. Thank you Nicole from Nicole Cruz Engagements for helping Jimmy create the most amazing ring ever. Thank you Crystal for being there to capture these special memories. Thank you to our amazing friends for driving all the way to St. Augustine to share this evening with us (and thanks for all the drinks!). And most importantly, to my FIANCE for making me the happiest girl in the world!!!

Sorry ladies, he’s all mine ๐Ÿ™‚



Here are a few of my other favorite pictures from the night:

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Leave a comment

  1. July 11, 2014 / 12:16 am

    That was a great read, love you guys

  2. February 6, 2014 / 9:10 am

    Congratulations!! The photos are great and he did an awesome job getting everything together. I might have gotten tears in my eyes reading this.

    p.s. Gorgeous ring!

    • Blakeley
      February 6, 2014 / 3:36 pm

      Thank you!!! Yes, he did a fantastic job with everything (including the ring!) ๐Ÿ™‚

  3. January 9, 2014 / 2:58 pm

    I was just asked to forward this to someone so after I did I decided to read it once more. Thanks for making me cry AGAIN! I don’t know how I am ever going to get through this wedding. My baby girl is finally getting married!!! Love you J & B!

  4. January 6, 2014 / 9:42 am

    What a fabulous proposal! Congrats on your engagement!

    • Blakeley
      January 8, 2014 / 8:10 pm

      Thank you!!! It was absolutely perfect ๐Ÿ™‚

  5. December 22, 2013 / 9:13 pm

    Yay!! So happy for you! I love how details your write up is. I feel like I was right there!!

    • Blakeley
      December 23, 2013 / 8:40 am

      Thank you!! It was pretty tough summing up a perfect night in a blog post, but glad to hear it translated nicely. Love you Stacey!

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