We're halfway through Arrow Season 5, and the Season 1 flashback arc will come full circle by season's end. Part of that mystery is how Oliver ended up back on the island where he was originally stranded, Lian Yu, after making his way through Japan and Russia. Ideally, the final episode of Season 5 will show us what happens in the moments before the series premieres and Oliver is running across the beach to get the attention of a passing fishing boat.
A few episodes back, it was revealed Talia al Ghul is the person who pushed Oliver to become Green Arrow-- even giving him the first Hood costume and making him practice in the Russian streets. She hands Oliver his father’s list and says he must do right by the citizens of Star City, which suggests she’s the one who will somehow get Oliver back to the island and organize his rescue. At least, that’s how it appears right now. We still don’t know exactly how Oliver’s relationship with Talia ended, since we heard nothing about here for the first four seasons of Arrow. But ever since Oliver realized he and Prometheus were trained by the same person in Russia, he’s been on the hunt to find her.
While we have yet to see Talia in present day, a recent development from Entertainment Weekly’s spoiler room gives a few hints about Oliver's return to the island. Executive Producer Marc Guggenheim doesn’t say anything specifically about Talia, but he did say Oliver will be returning to the island with a plus one, or two.
“I can tease that it will either be by boat or plane. I can also tease he won’t be going back alone.”
Unfortunately this quote doesn’t tell us too much--boat and plane are pretty much the only way to access any island. While Entertainment Weekly ’s questions seemed to be directed at the moment Oliver is rescued from Lian Yu in Season 1, we can’t necessarily assume that’s the exact moment Guggenheim is speaking of in this quote. It’s possible Oliver visits for another reason too. We’ve seen Dig and Felicity visit the island after Oliver retreated there after the events of Season 1. Oliver also built an AGUS supermax facility there to lock up villains like Slade Wilson in Season 2. Oliver and Thea also returned to Lian Yu to train to take down the League of Assassins in Season 3.
Arrow airs Wednesdays on The CW.