What do the TV Show Lost and Jonathan's dating history have in common?

In this episode Jonathan Wright watches the first 10 episodes and last 10 episodes of Lost (why??) and also delves into his extremely anxious dating history to answer the question of whether it might, sometimes, be good to get a little lost.

Sources

Chris DeVille, "Lost Was The Best Before It Was The Worst", Deadspin, https://deadspin.com/lost-was-the-best-before-it-was-the-worst-1635804502

Jen Chaney, "No, They Weren't Dead the Whole Time", Vulture, https://www.vulture.com/article/lost-series-finale-oral-history-the-end.html