06/18/2026
I Paid My Son’s Crush to Ask Him Out to Prom — When I Saw Pictures from the Evening, I Could Not Believe My Eyes
I know how this sounds. Trust me, I have replayed it in my head enough times to know that I crossed a line. But at the time, I convinced myself I was doing it out of love.
My son, Jeremiah, is a very shy, smart boy who has a really hard time talking to people. He is self-conscious; he stumbles over his words, and sometimes he gets so nervous that he just shuts down completely. But he is truly a kind soul, and he has such a bright, bright future ahead of him. He has already been accepted into one of the top universities, and I could not be more proud of him.
His high school years were heartbreaking.
He was bullied a lot. Kids were leaving him out of things. They called him weird. And Jeremiah would always pretend it didn’t bother him, but I’m his mother. I knew it did.
So when graduation came, I wanted to give him something special. As his graduation gift, he didn’t ask for anything because he truly doesn’t care about clothes or cars or expensive things. He just said he was fine. But I felt so heartbroken for him, thinking about how lonely and painful his high school years had been.
That’s when I did something I know a lot of people will judge me for. I reached out to the girl I knew he had a crush on since middle school.
Her name was Ella, and Jeremiah had liked her for years. So I messaged her and offered her a chunk of money to be nice to him on his last day of school at prom and ask him to go with her. She asked for some time to think about it, but in the end, she agreed. I knew she came from a poor family, and I knew the money would make a difference for her. I paid for her dress, her makeup, and her hairstylist, so we had ourselves a deal.
And yes, I know. I KNOW how wrong that sounds.
But at the time, I kept telling myself I was just trying to give my son one happy memory.
On the day of prom, she came over to our house, and Jeremiah had no idea about any of it. He was completely oblivious. We took some pictures outside, and he looked so nervous but so happy. My heart was breaking and healing at the same time. I wished him a good night, told him to have fun, and sent them off.
For the first few hours, everything seemed fine.
Then, a few hours into prom night, I got a message from one of the high school teachers.
It was written in caps lock.
"IS THIS YOUR SON?"
Before I could even answer, she sent another message. It was a PHOTO.
When I saw what was happening at the prom, my stomach turned.
