Planning the Perfect Proposal [5 Tips & Our Engagement Story]

If you guys follow me on Instagram or Twitter, you know back in May, my longtime (and I mean 5 years-LONGtime) boyfriend proposed while we were in New York City for our yearly anniversary/ birthday trip!
Before Thomas ever proposed, I knew he would far surpass all the "cute proposal ideas" I had saved to Pinterest over the years, and would make the proposal of my dreams look silly compared to the one he was going to give me. It's just his thing. He's meticulous, and regimented, and more than anything, incredibly detail oriented. This is the guy who looked at my Pinterest when we were first dating to get good gift ideas for me- he is what dreams are made of y'all! That being said, long before we ever got engaged, I knew I wanted to share his ideas on how to create the perfect proposal. 
Here are Thomas' 5 tips for a perfect proposal:
1. Do it when it feels right to you, and only you, to make it as special as it can be.
People are going to ask. They're going to ask you ALL. THE. TIME. Don't do it just because people are pressuring you. Wait until the time is not only right for you, but for both of you, and until you're able to give her the ring she really wants. You want it to be special.
2. Pick a place that sums up your relationship. 

I choose Central Park in New York City because we are a traveling couple and it is our travels that makes us feel the most happy. I think the best spot to do it for each couple is somewhere that you guys both love, or a theme that really fits your relationship. 
3. Tell your families at the latest moment possible to avoid spoiling it. 

I told both of our moms, and of course they promised not to tell anyone, but of course, everyone knew (including Tiff's nail lady, hah!). If you want to keep it secret, tell the least amount of people and wait until the very end to tell those few people. It will help keep it from getting out to her. If you're wanting a proposal where you are involving friends or family, obviously this would be even harder! Just keep it on a need to know basis. 
4. Say what you are feeling in the moment, instead of coming up with a rehearsed speech. 

I believe this is the best advice I can give someone who is looking for the perfect proposal. Trying to remember a speech will make you way way more nervous. Once you get down on that knee your heart will be pounding and you just say what you're feeling. It'll make it easier and more genuine if you speak from the heart in that moment.
5. Get it on camera to have the memory forever in print. 
If at all possible this is a BIGGEST one for the perfect proposal, especially in a girls eyes. If you can get it on camera or video she will be so thrilled! It will only add to how great the proposal can be.  Whether you set up your own GoPro, have a friend hiding in the bushes, or hire a photographer, just do it, SHE WILL THANK YOU! I'm so glad we were able to get a picture of our proposal to have for the rest of our lives to show our kids, their kids and whoever else. 

Using these five tips when you are proposing is sure to help you have the most perfect proposal!

If you aren't feeling any sappy love stories, you can stop reading now. But if you are in the mood for a couple of sappy love stories, here is our engagement story, written from both perspectives!

Her Story:
I should probably preface this by saying 1- it was SO hot when we got to New York, and 2- I get so cranky when I am hot and hungry. So..... Our flight finally landed in New York, we had been up since 3 AM and I was exhausted! Honestly all I wanted to do was get our bags and take a little 30 minute power nap and grab some lunch so we could explore the city on a full tank of energy! Thomas was rushing me to get our bags, and rushing me to get in line for the taxis! I knew the taxi ride was going to be rough, hello, I get car sickness from sitting in the backseat for five minutes! I knew our ride into the city was going to be brutal! And the heat! Oh my goodness, the heat! It was hotter there, then it was at home, in Texas! 
We finally got a taxi, and finally made it to our apartment in East Village, and I was nauseous, exhausted, and hungry! After a few minutes of getting our things settled, and switching from my purse to a backpack, we were ready to go. But before we left, I realized I needed to put something else on the backpack, but Thomas wouldn't let me even attempt to open it (HASHTAG OBLIVIOUS) which I totally attributed to all of his rushing. Nonetheless, we rushed out the door, with the promise that we would get food somewhere close to Central Park! 
It took what felt like forever to get our subway passes but we finally got on the subway and rode it two stops further than needed (first timers, duh), and seeing as how our first try didn't go so well, and I was even more nauseous at this point, we both decided it was best to get off the subway and walk in to the park! The first thing we saw when we got off of the Subway was The MET! I was completely enamored, but Thomas was having nothing of it, and rushed us past it.
We had both been in sandals for most of the day, thankfully we switched to tennis shoes to go into the park, but my feet were still killing me! AND if you haven't noticed, Thomas is almost a full foot taller than me, which means his legs are much longer than mine, and he walks 10 times as fast as I do. 
So we continued walking practically running to the park, just to get to "some dumb bridge!" We stood around taking pictures for a minute, and finally found someone to take our picture, so we didn't just have a bunch of selfies of us! The lady went on and on about how she hated when people took pictures from far away, so she wanted to stay up close. Which I was totally fine with! Thomas handed her my phone, and pulls the backpack off my back and starts to rummage through it as if he needed something out of there (STILL OBLIVIOUS). As we were standing there taking the pictures, and my head was on Thomas' chest (our normal pic stance) I literally felt his heart beating out of his chest! 
Two thoughts ran through my mind, either this boy is about to have a seizure (he was epileptic as a little boy and the thought of a seizure often floats in to my mind), or he knew something I didn't know....
The lady handed us back my phone, and asked if the pictures are OK, and of course I told her they were fine without even really looking at them. But Thomas immediately looked up at her and asked her if she could take a few farther back. I hand her back the phone, and attempted to step back into my place where we had just been standing, but as I turned to see were Thomas had gone, I turned right in to him, down on one knee! At that moment, I felt like MY heart was going to jump out of MY chest! I was shaking so hard, I couldn't even focus on what Thomas was saying, I just knew this was the part I was supposed to say "yes!" And I did!
His Story:
Flight had just landed in New York City and I was nervous as hell! Not that she would say no, but that she would notice the ring before we got to Central Park, or we wouldn't make it in time to do it and FaceTime our moms. 
We got our bags pretty quick and walked to get a taxi. After about 10 minutes in the taxi line we finally got one. An hour and 15 minutes later we made it to our Airbnb in East Village. In the few minutes she was in the bathroom, I was trying to figure out how to get the ring box and ring from my backpack to hers without her noticing. I was trying to put it in anything that would keep it discreet, like my sunglasses case, her makeup bag, etc and finally I just tucked it in the bottom of the bag. 
I was so nervous but totally under control. I was trying to get us outta there without being noticeable that I was rushing us to get to Central Park by a certain time. 
We made it to the subway station and after a few tries we finally bought our 7 day subway passes and were on the subway, moving on the 4 train headed uptown. Our first subway ride and all I could think about was what was about to happen when we got there. Without noticing, we accidentally got off the subway at 86th St. but we needed 77th St so then came the walking in the 95 degree heat. We were headed back south on 5th toward the MET and she was SO excited about the MET and I'm kept telling her "no we gotta go we gotta get to the park soon"! 
By now it was about 2:45 and I was getting worried because both of our moms took a long lunch together in Dallas so they could be waiting for us to FaceTime them, together, after our engagement. We finally got in the park, passed the Loeb Boathouse, saw the rowboats, and were in love with Central Park already! 
I was trying to get us to the Bow Bridge, and we could see it but I didn't think we were going to make it all the way over there, so we got to the Bethesda Fountain, and I decided that was the best spot. I was thinking about all the movies this Fountain was in, and how amazing it was. I told her I needed to get something out of her bag, so I quickly got it out and shoved the box down, in to my pocket and was holding it for dear life. 
I kept telling her we needed to get someone to take our picture and for about 5 minutes we had no luck because no on around us seemed to speak English. Finally we saw two ladies walking through the area and we asked them to take our picture. They said of course, and we began to pose. The ladies are taking some photos and they were talking about how they preferred people taking photos up close versus far away, so they were taking them pretty close. 
My heart was about to explode at this point and I was sweating so much from the heat and the nervousness and the death grip I had on the ring box. The ladies were about to hand the phone back to us and I was telling myself "don't blow the chance" so I asked the ladies if they could take a couple more photos from further back, even though I knew they had just talked about close up photos being better... 
I stepped back, behind Tiff and the two ladies gasp as they saw me pull out the box, and oh my God, all of these other people ran up and started taking pictures and Tiff turns around I am on a knee with the ring out (I had the box turned around, the wrong direction, true to my fashion, so I just left it there) and I just said "I love you with all my heart and I want to spend the rest of my life with you, will you marry me?" 
Tiff was then shaking out of control at the shock of it all! She said yes, and I put the ring on! Everyone around us was looking at the ring and we had a mini celebration with complete strangers around the Bethesda Fountain admiring the ring and how everything played out. Tiff was still shaking and could not stop smiling! I was so excited and still trying to grasp how perfect it was! We FaceTimed our moms and they were just excited as us and we could not wait to celebrate with them when we got back! I kept thinking to myself "what a start to the trip! I just made the best decision of my life and now the trip for sure is going to be the best trip we could ever imagined!" A trip of a lifetime and a trip that will always be on my mind and in my heart!

Did you have a perfect engagement story too? I wanna hear about it! Leave me a comment with your engagement story!


  1. Oh em gee! This story is absolutely adorable. I loved reading about the story from both viewpoints. I am not yet engaged, but I've been dating my boyfriend for six years... so I know it will be a good story once it actually happens. Can't wait to read all of your future wedding posts. Congratulations!


  2. ahhh love this story!! Congrats!! And to answer your question about my engagement story:

  3. Congratulations! What a great story!

    Carrie |

  4. This ring is beautiful!!! I loved hearing both sides of the story! So funny that your nail lady knew! Congratulations! :)


  5. Loved reading your proposal story and your ring is just stunning!

  6. All great tips, and I'm going to send this over to my bf ;) But also thanks for sharing your engagement story!!!you guys are so sweet :)

  7. Beautiful... congrats! For me, I told my husband the two most important things were that he involved my mother in picking the ring & that everything was caught on camera. He nailed it! xx

  8. This is so sweet! I would give anything to have photos of our engagement! So sad about that over 4 years later!



  9. Congrats girl!! That is SO amazing. And your ring is absolutely stunning! So cute to see both of your side's of the stories.

  10. Love your story! And your ring is so gorgeous! Congrats!!! ������

  11. Amazing tips! Congrats girl your ring is gorgeous!

  12. Congratulations! I also got engaged in Central Park though mine was far less refined than yours. I'm currently doing a wedding planning series over on my own blog (and I've shared my NYC proposal story as well). We should totally collaborate sometime!


  13. Congrats! What a beautiful story!

  14. Congratulations! Getting engaged is such an exciting time!

  15. This ring is beautiful!!! I loved hearing both sides of the story! So funny that your nail lady knew! Congratulations! :)


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