The Engagement

Before reading this post, you have to promise me that you won’t think any less of me after reading it. Do you promise? OK. I have decided to write about the worst thing I’ve ever done, which—in a way—is one of the best things I’ve ever done too, depending on who you ask. Brace yourselves for a long post, but it’s worth it. This is the story of how I toyed with the emotions and crushed the hearts of 378 teenagers at once.

For two summers, I worked as a resident advisor in a state program for gifted rising high school seniors. I participated in the program when I was in high school, and it completely changed how I saw myself and how I thought. Call it an “aha” moment. I loved working for the program that gave me that change.

The program itself establishes somewhat of a utopian society for several weeks. There’s little contact with the outside world, but the bubble within it creates an extremely close community that challenges its students to grow and think in different ways. I know… it sounds like a cult. If it is, it’s a good one.

Being an RA for this program is not just making sure the students living on your floor don’t die. The RA’s are the faces of the program. They lead deep seminars twice per week, manage events, hold nightly hall meetings, take kids for medical treatment, chaperone field trips, serve as counselors. The list goes on and on. It’s actually exhausting, but it’s the most fun job ever. Anyway, the only thing you really need to know about the job is that the students idolize the RA’s. They are sort of obsessed with our lives and they look to us as role models. And I took that role and crushed their adolescent spirits.

The students always think the RA’s are dating each other, and it’s a long tradition within the program for the RA’s to not confirm their suspicions, but to not deny them either. Why? There’s really no other reason except that we like to mess with them. Don’t worry, it’s all in good fun. So, we spent the first two weeks of the summer simply being a little flirty with each other and being seen with as many different RA’s as possible. The rumor mills ran wild.

The students would give us all the hot goss on the RA’s each night. I was rumored to be with three different girls within the first week.

As the program went on, the students finally came to a consensus on who the “actual” couples were (or so they thought). So after those couples were established, we ran with the rumored romances—the “RAtionships.”

RA’s would pair up and get coupley but not in obvious ways like holding hands or calling each other “Babe.” We would look at each other for just a little longer than normal, or laugh at each other noticeably, or sit beside each other more than we would sit with anyone else. Yes, we were terrible people, but the kids ate it up. They were intrigued with us.

Aren’t we deceitfully adorable?

My supposed RAtionship was with an RA named Elizabeth. We barely knew each other at the beginning of the program, but after apparently trying to hide our love for one another for the first couple of weeks, the students figured out that we were hot and heavy.

I must now inform you of another element of being an RA for the program. Every Monday there is a community meeting for announcements, but at the end of the meeting, the RA’s put on what is called “RA Update.” We created skits that lightly poked fun of the students and faculty shenanigans and we held a fake news report similar to “Weekend Update” on Saturday Night Live. It was our favorite part of the week, and it was for most of the students as well.

During RA Update, a recurring skit was a spoof of The Bachelor. It made fun of the countless relationships forming within the students as an RA was to pick another RA, with whom to fall in love. You’ll never guess who the bachelor was.

That’s right. Yours truly.

I spent the summer dwindling down the female RA’s through hilarious scripted comments as the students rolled with laughter. But it got down to the final week with only two contestants left. You can already guess that Elizabeth was one of those final contestants.

I hope you’re still with me, because all the previous writing was just for context. Betrayal is coming.

The students already knew I would pick Elizabeth because we were in love and whatnot; it was too predictable. We needed a season finale of The Bachelor that was legendary. And that’s when one of the other RA’s had an epiphany.

“You should propose to Elizabeth,” he said.

Other RA’s agreed that would be a good ending.

“But no, not just as the end of The Bachelor. You should propose to her and make them think you’re using the fake skit as an opportunity to propose to her in real life.”


I didn’t think about it long. If I would have, I probably wouldn’t have gone through with it.

But I said yes to the charade, and so did Elizabeth. And we concocted the most epic fake proposal of all time.


RA Update was always cheesy, but when it got down to the time for me to “choose,” I took Elizabeth by the hand and led her to center stage. As I did so, things switched from cheesy to heartfelt.

ALL the other RA’s, including the “contestant” I didn’t “pick,” came out on stage and formed a semicircle around us. Two of them eventually went to the crowd to video and take pictures to help sell the act.

With an expression as sincere as I could make it, I said, “I choose you, Elizabeth. I’ll always choose you. I know this whole RA Update thing is fake, but the last year I’ve spent with you has been the most real thing I’ve ever experienced.”

Cue gasps from the audience. Again, we basically just met a few weeks beforehand.

I went on to say how she was my favorite person and about how I loved her.

Cue “Aweee” from the audience.

I, then, said I wanted to spend the rest of my life with her. She began to look shocked. I got down on one knee and I pulled out a ring that we had borrowed from another RA. As I was doing so, there were actual screams of joy from the students.

“Will you marry me?” I asked.

With her hands over mouth, she shook her head up and down and said yes. It would have been a very beautiful moment if there had been an ounce of truth to it.

The moment.

Those kids lost. Their. Freaking. Minds. They all jumped up and shouted. I am not exaggerating when I say that over half of them cried.

The other RA’s embraced us in a huge group hug. They were all smiling, expressing their joy, and trying not to burst out laughing.

And we didn’t just automatically tell them that what they had seen was a completely staged affair. Elizabeth and I happily walked of stage holding hands, and the rest of the RA’s continued with RA Update. The students had about five minutes of believing they had been part of the most special moment in our lives.

And then we tarnished that moment.

We walked back on stage hand-in-hand.

I spoke.

“Elizabeth and I want to thank you so much for all your love and support.

We also want to thank you for creating this fake relationship, because we just met five weeks ago and we just GOT ALL OF YOU.”

They erupted again, but this time, with not so much joy.

They screamed. And booed. Their mouths hung open. Some of them cried a second time. Elizabeth and I walked off stage as one of the anchors said, “And that concludes the most epic finale in RA Update history.”

You can imagine the outrage.


After that, I was Public Enemy Number One and Elizabeth was Public Enemy Number Two. Most of the students let it go after a while and things went back to normal. But for a couple of days, they DESPISED me. It’s all they would talk about. My following nightly hall meeting entailed nothing but the sound of my voice as 24 boys stared at me with disapproving eyes. I crushed them. After a few long, and very heartfelt, apologies they forgave me. I think.

I learned a few things by pulling the incident.

1. I’m a much better actor than I had thought.

2. If you’re messing with people, know where the line is. I may have straddled it when I caused several teenagers to cry.

3. People get entertainment out of other people’s emotions—good or bad. Just as viewers invest in reality TV shows, the students were obsessed with the RA’s dating each other, and the RA’s wallowed in slightly crushing their souls.

4. Don’t lie to the people you care about. I haven’t mentioned that the guys on my hall accidentally found out that I was proposing to Elizabeth, but they weren’t informed about it being fake. They were so excited to be part of  my “big day,” and I actually hurt them a little when they found out that I wasn’t telling them the truth. I really did feel bad.

Did I pull of the biggest punk’d moment that I or those kids had ever seen? Absolutely.

Did I feel guilty about it? A little.

Do I regret it? Nah, not really.

After all, they created the relationship in the first place.

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