video by Brian Braganza, Man Sum Lai, Joseph Lautrup, Lisa Nho, and Erica Solano; production by Nadia Suleman; commerce strategy by Alexandra Miguel; photography by Rachel Stern for TIME.

Thirty-seven year old Winnipeg-based accountant Jordan Abrams, a proverbial doormat of a man, has pined after Rachel Stern since he was twelve. He finally got her to be his girlfriend last year ...