TB’s How-To (Learn from my mistakes) Guide to Planning a Proposal


When I decided to start my blog with our proposal story, I thought it was fitting to ask my fiancé, Ty, to write the first post.  I wanted him to be able to tell his side of our proposal story and how I made it rather difficult on him at times (something we now laugh about frequently).  That turned out to be a longer story than I even realized at the time (I screwed it up for him several times), so my first two posts will be authored by TB (as I call him) so you can get the full story in his words.  I now love hearing how proposals didn’t quite go as planned, so please share your stories in the comments!  Enjoy!  – Christy

We’ve all seen the Hollywood version of romance. The Notebook, How I Met Your Mother or a host of other romantic comedies. It’s a simple formula. Guy meets Girl. Romantic things happen. Plucky best friend helps in some way. Guy does something stupid. Somehow, Guy works his way back into Girl’s good graces, and then it happens. Guy pops the question to Girl… doves fly, planets align, and everything is perfect…

The one thing all these films have in common is that the world makes it relatively easy on the guy. Things just work out. These guys have never fallen in love with a wedding planner.


(Photo Above: Taken shortly after we started dating in 2014… back before I knew what it meant to be dating a wedding planner)

CB is the absolute love of my life. She’s the best thing I could ever imagine happening to me. Do I still do stupid things? Heck yes, I do. Does CB tolerate my random and wild nature? Heck yes, she does. She loves me too.

What’s the real reason I’m writing this? I’m here to tell you about my experience in proposing to a wedding planner. While on one side of the coin CB is a lovely woman, on the other side she’s a highly skilled operative intent on turning over any detail to find out information. She is ruthless and will stop at nothing to find out what she wants to know.  What we basically have is the perfect romantic storm on our hands. A good relationship, 10 years of planning other people’s weddings, and me attempting to ask CB to marry me.

Formulating the Plan

So, knowing that, where does one start with the proposal? I started with her good friend. For protective reasons, and if I’d like to use her for covert ops again, let’s just call her SH. SH and I met earlier this year, so I could bounce ideas off her, get her feedback on the ring design I’d been working on (with the help of a jeweler friend), and to just bring her into my thought process. SH quickly let me know she’d been waiting forever on this and was glad I’d finally decided to ask. OVER THE NEXT FEW MONTHS I HEARD THAT SAME STATEMENT FROM EVERYONE. And a bit of advice for all the guys out there… If the time is right for you just ignore the foolishness. You’re a grown man and you can ask on your own time. Don’t let others push you. But, I digress… SH helped me plan out ideas for a sweet proposal that involved our family and friends, a great place to have it, and what photographer to book. Easy and wrapped up with a bow on it.


(Photo Above: Little did she know that planning was well underway when this was taken earlier this year)

You may be wondering if that’s it. Sounds like you got your Hollywood style proposal. But no, that’s not it.  Remember, CB is a wedding planner… and I made some dumb slipups.

Let’s talk about the advanced intelligence part of the lovely CB mixed with my mistakes.

Things not to do if you want a proposal to go as planned:

  1. Do not leave material about venues in your person’s vehicle.
  2. Do not tell more than one person. DO NOT EVER TELL MORE THAN ONE PERSON.
  3. You are not smarter than your person. Ever.
  4. Be careful if you’re texting someone in your person’s presence. If it’s someone outside your normal circle, they will become suspicious.
  5. If your girlfriend runs your calendar, you’re already screwed.

How I overcame or failed in my mistakes:

  1. I messed up and left a folder from the proposal venue in CB’s vehicle, she obviously found it and started asking questions.  So, I had to move the venue and completely change the plan. But, it only takes one step for your person to begin to become suspicious. Verdict…Fail
  2. A few weeks before I planned to pop the question I got a random phone call from a person outside our close friend circle. “Hey TB! I heard you were having a party after you and CB get engaged and we would love to come!”. I played along and said of course you all can come. I hung up the phone and immediately went back to the drawing board. I understand that people are so excited for you that they can’t help themselves. But, learn from me and be very selective while keeping the group as small possible. Verdict…Fail
  3. CB is an interpersonal ninja and watched me like a hawk once she became suspicious. You are not smarter than your person. You are not sneaky. They may get an idea it’s coming but never admit to it! Your person will make it rough on you. It will be amazing if you can hold it together and execute something they will love forever. It will also make some great stories later when you can tell them how hard they made it on you.  Verdict…Draw
  4. When I first started planning I was texting vendors, venues and the wonderful jeweler, Meg C constantly. This was a dumb move. A terribly dumb move. Email everything and turn off notifications. Open another email account if you must and only access it through your web browser. Does it sound paranoid? Maybe. But nothing is worse than your person starting to get suspicious of what you’re up to. Once that happens they are going to be constantly watching and thinking it could happen any minute…unless that’s what you want…  Verdict…Win
  5. CB has a terrible habit of over filling everything. In a single overnight trip CB can have us visiting her entire giant family at all their houses separately. CB has stuffed a cupboard so full that one tiny bottle of paprika being removed will create an avalanche of more spices than the Colonel uses on his delicious chicken. She says it’s not being a pack rat but a “good use of space”. But again, I digress. We had a weekend trip to Lexington (our former home) planned.  My sweet CB noticed we had a free night near my birthday while on that trip. Empty agenda + CB… Commence the planner brain. So, CB decided to throw me a surprise birthday party. You may think, “What an awesome thing to do!”. Well dear reader, you couldn’t be more wrong. I had been working with SH to plan our proposal/surprise engagement party the very same night. AT THE VERY SAME PLACE. CB is a plan ruining psychic. Luckily, I’m friends with the owner and he gave me a heads up. If it’s near a birthday and there is free time, it’s a recipe for disaster. Verdict….Fail
(Photos Above: Taken the night I was going to propose, but instead CB threw me a “surprise” birthday party)


After I decided to scrap my first plan I began to think about what CB would enjoy the most and not what I thought she wanted. I thought she wanted the proposal to happen, get a few minutes by ourselves, and then straight to a party to celebrate with all our people. I thought she wanted something that was more wedding planner than “us”. No matter what don’t think about what you want or what she thinks she wants – think about the “us”. If your “us” is New Year’s Eve at the top of a water slide in Dollywood then you do the hell out of your version of “us”. Once I started thinking about “us” the proposal perfectly evolved from there.  Our version of “us” turned out to be a romantic hike in the misty mountains of the Pacific Northwest.

To be Continued… 


  1. reelspecial says:

    Love that you had the future hubs write the first post! 🙌 Congrats on your engagement!!!

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