My Secret Operation To Get Engaged And How It Almost Went Wrong

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OutKick family, I am officially engaged.

As anyone who follows me on social media or follows my fiancée Shelby on social media knows, I got engaged Friday. It’s been a long time coming, I couldn’t be happier and I am excited for what the future holds.

However, this situation runs much deeper than the public might realize. This was no simple engagement. This was no simple evening. This was no simple event.

Immense planning was put into an engagement operation…..and it was all nearly lost at the 11th hour before I called an audible that would make Tom Brady proud.

This is the story of Operation Hooked On Hookstead.

The engagement plan was perfect…..right up until the moment it wasn’t.

Let’s start with a little backstory before we dive into the meat of everything. Shelby and I met working at the Daily Caller back in 2019. We started dating shortly after she lost a bet to me on the Iowa/Wisconsin game. Story for another time. Now, it’s summer 2024, and we’re engaged.

Once the decision was made to propose, a plan was immediately created and developed about how I’d go about doing it. Much like the guys I interview, operational security is key. The more people know about something, the more likely it is that it leaks. The last thing I wanted to do was ruin the surprise for Shelby.

There were three people in the world who knew of Operation Hooked on Hookstead. A woman who goes by the name MMO, a close friend of mine we’ll just refer to as WD and me. Not my family, not her family, not any other of her friends and not a single other friend of mine.

To be clear, both our families and all our friends knew an engagement was going to happen, but none other than MMO and WD were read into the operation details. The three of us made up the sole team responsible for planning and executing the operation.

On the surface, the operation seemed like it was going to be easy. Shelby was in Atlanta to watch the Trump/Biden debate, and would be returning Friday. MMO would be used to lure her out of the Hookstead compound (location classified), and while MMO had Shelby entertained and out of the house, I had an entire setup planned. She’d return to the finest chocolates, roses, champagne and a video I made would be playing on the big screen in the living room. She’d never see it coming. As soon as she accepted, we’d go to her favorite restaurant for a private dinner and then meet up with MMO and WD for drinks at The Haymaker and Dirty Water – Shelby’s favorite bar and then my favorite bar.

I had this planned down to the exact minute. However, before MMO could get Shelby out of the Hookstead compound, she ended up being scheduled to an in-studio hit on a big TV network (yeah, my fiancée is a rock star on TV). No big deal. This changed nothing. Instead of setting up while she was gone with MMO, I’d just set up while she was on TV. Super easy.

But even the best made plans can be derailed.

The network ended up switching her to a remote interview that she would shoot from my in-home studio. I now had a *HUGE* problem on my hands.

How the hell am I supposed to set all this stuff up if she never leaves the compound? Furthermore, I have a bunch of chocolate, roses and champagne that she can’t find because it’s going to be obvious something is going on. The wheels started spinning in my head. Do I delay the proposal to a different day? Is it possible to pull off with her actually in the compound? I’m not going to lie. I was getting pretty anxious.

Eventually after consulting MMO, the decision was made to proceed as planned and blitz the setup while she’s in the studio live on TV. I have roses hidden under the kitchen sink, the ring had to be moved to a secure secondary location, chocolates were hidden under the bed and the champagne was actually hiding in plain sight.

I made up some BS excuse about being on a meeting starting at the same time as her in-home studio, and I needed her to stay in there once she went in so that the noise of her opening doors and such didn’t screw up what I was doing. It was a very flimsy and weak excuse, but it was all I had.

If Shelby walked out of the studio – which is within spitting distance of the living room – then she’d see exactly what I was doing and the surprise would be ruined. I was about to test fate.

I could hear her go live on TV, and I knew I had at most maybe 10 minutes to get all this set up. Maybe as little as five. Anything less than a perfect setup before the studio door opened and the entire surprise and event would be ruined. I rush to put on my finest clothes, grab the champagne and glasses, get the roses, retrieve the chocolates from under the bed, get the ring from the secure secondary site and put on the video I personally made on the big screen.

It was all done in about six minutes. I ended up having two minutes to spare. She walked out of the studio, and was in a state of shock. I’ll fast forward over what happened during the actual ceremony because it’s nobody’s business but our own, but I will say we were locked in on schedule as planned. A potential disaster had been avoided. If she’d looked in the first or secondary secure sites and noticed things had moved, she’d become curious. If she opened the sink and moved the soap, she would have found the roses. If she looked under the bed, she’d have found the chocolate. It’s a miracle the operation wasn’t blown. Is it better to be good or lucky? It’s best to be both and that’s what I was Friday.

A look at the working class ring! (Credit: David Hookstead)

With the target secured, it was time for the rest of the planned night to unfold. We hit up the Little Grand for dinner, hit up The Haymaker where I had my first ever espresso martini (I had two and both were great!) and then hit up Dirty Water for some music and beers with the boys and an expanded crew.

Pizza at the Little Grand. (Credit: David Hookstead)

Dirty Water is without question my favorite spot in D.C., and the owner had the place rocking for our engagement celebration.

Did we also play Toby Keith’s “Courtesy of the Red, White and Blue” as we sang our butts off? You bet we did!

And that’s the story of June 28, 2024. The smallest of margins and absolutely no room for error nearly ended in disaster thanks to a TV network throwing a huge wrench in my plans, but all is well that ends well. I appreciate everyone who reached out to congratulate me. I’m way behind on texts and emails. I’ll get to them all eventually. In the meantime, I have some more celebrating to do! Let me know your thoughts on the story at David.Hookstead@outkick.com.