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The in-game gay marriage proposal that still makes me cry

Jake Conrad’s proposal to Michael Holtzman at a 2016 Bulls game still gets our Ken Schultz. Every. Single. Time.

This is without question the best thing that has happened at a Bulls game since 1998.

Something to know about me: I’m not a fan of in-stadium proposals. When such a moment interrupts a game, whatever romance exists in the moment of two soulmates making things official tends to get wiped out by its placement somewhere between the t-shirt cannon and the sausage race.

And... well... there’s always the chance that things will go disastrously wrong and said soulmates will realize that at the most emotionally vulnerable moment of their lives, they’re surrounded by Boston sports fans. Welcome to hell, lovebirds.

Something else to know about me: underneath all of my snark, sarcasm, and Prince references, I’m just a big ol’ softie. The last ten minutes of Love, Simon leave me nearly catatonic with a case of the feels. YA novels like What If It’s Us are my gay Pixar. I can sing along to every lyric to One Direction’s “What Makes You Beautiful.” The end of this paragraph couldn’t get here fast enough...

So back in December of 2016 when video hit the internet of a gay marriage proposal at a Chicago Bulls game, my inner Simonverse-fanboy tween got the better of me. I clicked through and dear reader, I embarked on a two-minute transformation into a weeping mess. In all of the best ways.

As the clip starts, this being an NBA game, it becomes clear that the Bulls are trying to choreograph the moment within an inch of its life. The lights are dimmed, the Luvabulls break it down to “Do You Love Me,” Benny the Bull works the millionaires in the courtside seats... it actually gives the worrisome impression that a special moment is about to be overwhelmed by marketing-laden spectacle.

But once the camera pans over to Jake Conrad and his unsuspecting soon-to-be-fiancé Michael Holtzman, that’s when I start getting that feeling around my head and shoulders that I can only describe with the phrase “assume the swoon position.”

The two of them are so real and honestly awkward in the moment that I can’t help but immediately connect to everything they’re going through. Michael clearly wants no part of getting pulled out on the court by Benny. Jake is unsuccessfully trying to contain every emotion that wants to explode beneath a nervous smile as he’s being led to the opposite end for the big reveal.

I know what the result of all this is going to be. I can see it in the title of the video. But in watching it all play out, the spoiler doesn’t matter. I’m still in, rooting as hard as I can for the happily-ever-after ending.

Once the emotional connection is made, the wait for the big moment feels interminable, even though it’s less than half a minute. Benny the Bull spins his unwary dance partner around to spruce up his look as Jake gets into place. Then Benny turns Michael around to face Jake just as the music stops.

If this were a YA book, this is where I’d add something like “So does my heart.” Seeing the realization of what’s about to happen hit Michael is one of those rare moments where you realize everybody involved got this exactly right. It’s also the time where I realize whatever mental protector that tries to block me from crying in public isn’t nearly strong enough.

And the ring pop as he Jake takes a knee... I’m not normally one to type the words “I can’t even” but... I can’t even.

If I had to hazard a guess, I think part of why I tear up watching this is because I’ve seen this scenario play out numerous times at games I’ve attended. Everyone claps, a few wise-asses yell “NO,” and then the game restarts. But I never really identified and connected with it so personally until I saw a gay proposal presented in the same way — and be greeted with the same burst of joyous noise from the crowd.

It’s both extraordinary and extraordinarily normal at the same time, which is what makes it beautiful. It’s hard for the 20,000-seat United Center to get real dusty inside. But this does the job.

Shortly after the proposal video went viral, we wrote about how Conrad planned it as a surprise for longtime Bulls fan Holtzman’s first game in person. It’s a great story of how what started as a much smaller idea turned into such a big moment. Eventually, their proposal became so closely associated with the team that the Bulls invited Conrad and Holtzman back for their 2019 Pride Night and to be part of their float in the Chicago Pride Parade.

Usually when sports make me cry, it has to do with something on the field. But as this video shows, there are times when the most extraordinary things happen during a time out.

What are the sports moments that made you cry? Let us know in the comments!