The story of How I Met Your Mother followed Ted Mosby as he told his kids the long and involved tale of how he ended up with their mother. At the same time, the lives of his friends were intertwined in the narrative. That included Lily Aldrin, who was married to Ted's closest friend Marshall Eriksen. But before there was Marshall, Scooter was Lily's boyfriend. And as hard as he tried, the guy was never going to win Lily back.
Lily was born in 1978 and raised in Brooklyn by an ultra-feminist mother and a board game-obsessed father. She would eventually attend Wesleyan University, where she focused on studying art. This would lead to her first profession as a teacher and then as an art consultant to a very wealthy man referred to as The Captain. It was an interesting career move, to say the least.
During her time at Wesleyan, Lily met both Ted and Marshall. Lily was immediately interested in Marshall, breaking her own stereo and asking him to fix it as a means of getting some alone time with him. She essentially constructed their meet-cute. While their relationship wasn't always easy, that didn't change the fact that Lily and Marshall were meant to be together. As such, poor Scooter was pretty much out of the game as soon as these two met.
In the early 1990s, Lily was a high school student in Brooklyn and she wasn't a particularly nice person. In Season 4, Episode 6, she revealed that she passed gas in class rather loudly. Rather than accepting the blame for her actions, she let the guy sitting next to her take the fall and helped nickname him Gasser. Things weren't much better for Scooter, the neighbor boy Lily literally bullied into dating her.
Scooter wasn't even his real name. It was Jeff, but Lily forced him to change it to Scooter. Despite being a somewhat unwilling participant in the relationship at first, he actually fell quite in love with her. That was something that never went away, even though Lily dumped him at their prom. She didn't want to go to college while still being attached to a high school boyfriend.
Even after Lily and Marshall ended up together, Scooter never gave up hope that he would reconcile with Lily. Apparently, her bullying him into caring about her stuck much better than she wanted it to. He even went so far as to take a job in the cafeteria of the school Lily worked at to stay close to her. And he showed up at their wedding in Season 2, Episode 21, failing to win her back during the ceremony.
The crazy part was that Marshall might have been Scooter's biggest supporter. He was actually rooting for him at times, telling Scooter to stay positive, as he wouldn't live forever. Scooter's ultimate act of obsession was marrying Jasmine, a stripper who looked identical to Lily. It's too bad that he couldn't move on from Lily, but in Scooter's defense, she did make it incredibly hard for him to do that.
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