Doug meets Lil early on in the story, and they are united in friendship around the town library and his job at her father's shop where he is the delivery boy. Doug encounters many hardships and some adventures and, though he has Lil's friendship, he is so preoccupied with his misfortunes (and sometimes small triumphs) that Lil doesn't rise high on his emotional barometer for much of the story. Yet when Lil faces her own hardships, her place in his emotions is deepened and his loyalty to her is evident. So while it takes the duration of the novel, Doug and Lil both come to love each other. What hardships and triumphs do they experience to bring them past loyalty to young love?
Doug's central hardship is his family. Because of the antagonistic and brutal situations he faces at home, Doug has problems with everything, including education, sports and attaining people's trust and respect, especially that of the principal and his coach. One major victory Doug has is in wining Lil's friendship.
Another of his few victories is that he is befriended by Mr. Ferris, his science teacher, who arranges reading lessons for him given by the English teacher, who also befriends him, after realizing Doug won't read because he can't read. Another victory is the friendship of Mr. Powell who successfully teaches Doug to draw and paint. His most significant victory and biggest adventure is the recovery of the Audubon photographic plates that belong in--and are returned to--the town library because of Doug's clever negotiations and deals. He has the honor and adventure of having his own painting replace the one that was taken overseas. His greatest victory is in attaining self-respect and learning to trust his own mind.
Lil's overarching hardship is that she develops a life threatening illness, which reveals itself the night she and Doug are to go onstage, then undergoes chemotherapy. She is expected to die as only one in four can survive. Her greatest victory, then, is that she survives. Her determination is rewarded with life and with the added benefit of Doug's promise of love and care always.
In Okay for Now By Gary D. Schmidt, Doug eventually falls in love with Lil. Doug starts off by falling in love with writing, specifically the works of John James Audubon. Raised in an abusive family, Doug does not understand why love is important until he meets Lil. He sees the difference and uniqueness in her, slowly gets to know her, and eventually falls in love with her.