Love at first bite: How we got engaged to scam Cracker Barrel out of $2,000

For clarity, italics indicate that Will is speaking and bold text indicates that Jayden is speaking.

The best things in life are free – love, biscuits, etc. The second-best things in life are acquired through mischievous means – love, biscuits, etc.

In honor of Valentine’s Day, Cracker Barrel created a contest to give away a free year’s worth of meals in the form of $2,000 in gift cards.

You just had to do one thing to enter: get engaged. At a Cracker Barrel. And record it. And post it on Instagram. And have your mom freak out (this part isn’t required for the contest, but it’s likely to happen).

So, we did what any two sane people would do: got engaged. At a Cracker Barrel…you know the rest. 

For the record, this was all Will’s idea.

For the record, this was all my idea. 

Before we get too far into the story, we should clarify: we are not really engaged. Sorry Cracker Barrel (and also my friends from high school who sincerely congratulated us), you have been fooled. 

Our initial plan was to get a group of our friends to also do fake engagements. The contest could have up to five winners and the more entries we had, the more likely we were to win. How many people would actually get engaged at a Cracker Barrel? We figured we wouldn’t have much real competition and having multiple entries would guarantee a win.

We got plenty of people to say they liked the idea, but we didn’t get any people to say they wanted to do it. Apparently proposing at a Cracker Barrel and posting it publicly to Instagram is “really embarrassing and weird.”

In the end, we had to settle on just one fake proposal and bank on that being enough to win the contest. We just had to make sure the proposal was good enough to convince the Cracker Barrel judges panel. 

We went to the only Cracker Barrel in town a few days after Valentine’s Day to avoid the real couples celebrating their love and as many people as possible. The goal was to make the proposal as cute as possible without getting a single person to notice us.

I supplied the ring and the ring box – a Christmas gift I’d gotten from my parents.

I supplied the cuteness – an important part of a cute proposal. 

We filmed ourselves walking into the store and messing around in the world-renowned Cracker Barrel gift shop to make it more believable. We also sat down and enjoyed a meal to make it more believable. We also asked for more biscuits three times to make it more believable. 

After eating, we went outside and set up our camera on a barrel (presumably full of crackers) that was in front of part of the restaurant where no customers were sitting. We decided this would be the ideal place to propose so no one would see it, but you could tell it was at a Cracker Barrel.

As we were preparing to film, a bus full of families pulled into the Cracker Barrel parking lot and we began to panic.

Will got down on one knee as fast as possible. I probably should’ve tried to fake cry, but I didn’t want to draw more attention to this already stupid idea – unlike Will, who picked me up and spun me around.

I like to spin. You should see me in our office chairs. 

After editing together, the video and coming up with a cute little caption, we uploaded it to Instagram and waited. We patiently stalked the contest hashtag to see other posts and if we had any competition. 

Will did not “patiently stalk.” He looked at that hashtag every day. He would count how many posts there were. He would show them to me and be like “there’s just no shot that they can beat us.”

I am a competitive person. I like to engage in a little trash talk, and I like to win. 

Then, six days after we posted the video, we received the notification we had been dreaming of: Cracker Barrel has DMed you. 

We won the contest. 

After giving Mr. Barrel our emails and signing some documents, our free year’s supply of Cracker Barrel in the form of four $500 gift cards arrived along with a handwritten note congratulating us on our engagement. 

You may be asking yourself, “Is it ok to lie?”

To that we would say we didn’t lie. There is no legal definition of an engagement and there was never a stipulation that we had to actually get married. I did propose which was the only real requirement. 

Did we mislead? Yes. Did we lie? No. 

You may then ask, “Well even if you didn’t lie, isn’t it unethical to mislead someone like this?”

Unfortunately, you can’t hear our response because our mouths are too full of biscuits.