According to one theory (via Reddit), the pair had a specific reason for avoiding each other: Chewbacca was observing a Wookiee mourning ritual. Based on Wookiee customs, Chewbacca could not seek comfort from others yet, but he could still work to save others.
Leia kept Han's medal as a treasured memento of her dead husband. She held it before reaching out to her son, perhaps somehow connecting to Ben and Han's presence in the not-so-living Force.
The ancient smuggler queen was eager to see her boyfriend Chewbacca – and curious what favor Han needed this time. When Han asked her for help getting BB-8 to the Resistance, Maz said the journey wasn't hers to take – it was Han who had to return to Leia Organa after their long years apart.
Leia wanted to lead and reshape the galaxy, but wielding the same power that had corrupted Vader would be too big of a temptation because she would have become a powerful Jedi. So, it was safer to choose happiness, marry Han and avoid becoming a Jedi.
Chewbacca with Han Solo. In 10 BBY, Chewbacca met Han, the latter who saved him from imprisonment. Chewbacca was so grateful for Han's intervention that he proclaimed a life debt to him; the two have been best friends since then, as Han gave him the nickname "Chewie".
New Star Wars Force Awakens Deleted Scene Would Have Changed The Movie For The Better
Why doesn t Chewbacca recognize Obi Wan?
In A New Hope, when Chewie meets Kenobi, Chewie knows he is a Jedi, but why doesn't he acknowledge him or why didn't they talk about what happened previously? Or why didn't they connect differently for the first time? Because Revenge of the Sith wasn't written yet in 1977.
After Solo's death, Chewbacca often served as the sole pilot of the Falcon, including piloting the ship to aid the Resistance during the Battle of Crait.
Leia's Force abilities and her lack of awareness of her true identity also contributed to Vader's inability to sense their familial connection. Vader's denial of Anakin Skywalker's legacy and his fear of getting hurt again prevented him from realizing the truth about his children until later in the original trilogy.
We see in legends and Canon that Leia is not the most invested in her jedi heritage. Obi-Wan didn't know there was another Skywalker until Yoda said something. Luke had begun Jedi training and it was easier to focus on one Skywalker at a time. A Jedi can only have one apprentice at a time after all.
Yoda may have wanted to train Leia instead of Luke, but he was wrong - precisely because he did not understand that the redemptive love of a son towards his father was what would bring balance to the Force. Fortunately, the will of the Force won out, and Luke was the one chosen to train as a Jedi instead of his sister.
She and her son were put in an Imperial slave camp on Kashyyyk. At some point, Malla was separated from her son Lumpawaroo, who became a child slave in Commandant Dessard's camp on the slopes of Mount Arayakyak.
Chewbacca had a wife named Mallatobuck and a son named Lumpawaroo. During the Imperial Era, Chewbacca was enslaved by Trandoshans. "Malla" and their son "Waroo" were also enslaved by the Galactic Empire and were put into an Imperial slave labor camp on their homeworld of Kashyyyk.
He was incredibly important, both to the galaxy as a whole and to Rey personally. While they may not have had romantic love for each other, they became close enough that Rey would miss him after his death. The kiss at the end of The Rise of Skywalker was a goodbye to a friend who would be dearly missed.
For all we know, Leia specifically channeled her own life force into Ben, helping Rey along and sacrificing herself in the process. That may be why Leia finally dies and fades away at the moment Ben revives Rey and fades away himself. When Ben dies, any tether Leia still had to the living world went with him.
When she's revived they briefly share an awkward kiss, and he vanishes. It seems that with his last ounce of strength, Ben gave what was remaining of his life energy to save Rey. This was his last sacrifice, effectively acting as redemption to return him to the light side of the Force.
Obi Wan was assigned to watch over Luke . To guard and quide him as best as he was able. Obviously Yoda's choice for Obi Wan to do so singled out Luke as the preferred Jedi candidate in the future. With Leia only as a last resort.
Leia was known to be force sensitive in ESB not ROTJ and the prequels make it clear that Obi-wan and Yoda knew from the moment she was born. The only reason she (and Luke) didn't know was because they were still figuring things out.
Her holographic plea for help, already iconic, will never be the same. She knows Obi-Wan's real name as well as his alias of “Ben.” When Luke comes barging into her cell and says, “I'm here with Ben Kenobi,” Leia jumps off the bunk in an instant. “Ben Kenobi, where is he?” she says, raring to go.
Darth Vader didn't learn he had a daughter until Return of the Jedi, when he stood before Emperor Palpatine. The Emperor's power probed Luke's mind, attempting to goad him to fall to the dark side, and he discovered Leia's existence. "Sister," the Emperor taunted.
Finally, Rey is Kylo Ren's aunt through Anakin Skywalker. This means that Kylo and Rey's romance is just as genetically awkward as Luke and Leia's kiss on Hoth was. Granted, neither pair knew they were related at the time, but that's no excuse.
Given Rey's lineage as Palpatine's granddaughter, it is also reasonable to assume she is already better attuned to using Force Lightning than the average Force user, with Ben telling Rey that she has all of Palpatine's power within her at the beginning of The Rise of Skywalker.
And that's why mere minutes later a character literally says "he must have been on another transport." It's storytelling at its laziest. Later in the film, it's clearly established that Rey can feel Chewbacca's presence on a ship from far away, and she learns that he's still alive.
