Episode 21 "Home Away from Home" ("Koromon, the Great Clash in Tokyo!")
This episode.
Tai's relationship with Kari.
Going into the series, I didn't know that Tai had a younger sister until he mentioned her. I didn't think she would be ever mentioned or seen in the series, but then he returns to Tokyo in episode 21. I felt like that episode was such a turning point for Tai's character. He could have abandoned all his friends and stayed at home with his little sister that he had great affection for, but decided not to. He realized that it was more important to return to the Digital World to defeat the rampant Digimon, which would in turn protect his younger sibling.
The moment of separation was so gut wrenching to watch in this episode and it left such an impression, so thus I tried to recapture that moment in my piece.
I have an older brother myself. When I was a child, I really wished Tai was my older brother. I wanted someone that could protect me and I could have fun with. I had that but there was also something off with our relationship, or at least how I perceived it. Something tarnished the relationship and I won’t go into detail about it here except say that there is another Chosen that I more deeply relate to which I’ll honorably mention in a DA Week bonus post.
While I don't have a fanart piece, Episode 48 "My Sister's Keeper" ("Bombing Mission! Mugendramon"), also gets honorable mention because we get a glimpse more of Tai's and Kari's relationship growing up. We see how reliant Kari is on Tai and wanting to not be a burden on him and Tai’s regrets for not being a better older brother and not being observant that his sister was sick. This plot shows how far Tai’s come and why Matt had every right to feel jealous of Tai being the ‘better older brother’.