He hadn't just lost some hair and gained a little weight – he was bald and he weighed 450 lbs.
He could only imagine what her reaction would be when she saw how much he'd changed from the 165-lb. boy with a full head of hair she'd fallen in love with.
"People look at you with sadness. Horror. Pity," Jordan, now 50, tells PEOPLE. "And this was the love of my life. I couldn't stomach her looking at me that way."
Instead, he got a pleasant surprise.
"Beth looked at me, and all she saw was Lee Jordan," he told CNN. "That's it. There was nothing but love and acceptance in her eyes.
Beth, now 51, confirmed it.
For Jordan, it was a turning point in his life.
He had just been diagnosed with obesity-induced breathing problems, diabetes and high cholesterol. He used an oxygen tank to breathe.
"The doctors had told me, 'You're going to die in two years,' " he tells PEOPLE. "And I still left the hospital and couldn't change."
The two, who had broken up in college, became friendly pen pals after that meeting in 2008 and Jordan immediately took steps to lose weight.
After Schwein divorced in 2012, their relationship became romantic. Jordan proposed in the same Starbucks where they'd met for coffee for years earlier. They are now married.
Jordan, at 5 ft., 8 in., now weighs 178 lbs. He is a certified personal trainer and works with Beth. They see clients though their company, Fullest Living, in Jacksonville, Fla.
There is a moral to this story, he says.
"Love and acceptance can move people past amazingly difficult barriers," he says.