He goes to the Crystal Temple in person and is greeted by Pearl. He nervously asks her out to lunch for tomorrow and while Pearl does not eat she would be okay with meeting him. Pearl tells the other Crystal Gems the mayor invited them and it would be a good opportunity to gain information on how to raise a teenage boy.
The next day at Seafood and Eat It! Amethyst, Steven and Pearl shows up much to Mayor Dewey's surprise/disappointment. Pearl explains that Garnet was busy looking for Malachite, Amethyst is eating, Bill mumbles quietly how this did not turn out as planned while Steven hears him. Steven, being a lover of schmaltz, decides to help the mayor be alone with Pearl.
After some antics, shenanigans and probably a Gem fight, Pearl and Bill are on the beach with no one else around. He openly and honestly reveals his feelings for her in which there is no way for her to misinterpret.
She blushes. Pearl is deeply flattered that someone could think so highly of her but she could never return his feelings. She admires how brave he is but the answer is no.
A week later Bill gets a call from Pearl. She wants to talk to him about growing human children and offers to meet a tea shop. From that started the weekly friendly meetup between the two. Sometimes they will bring others but it will always end with them. Bill talks about his concerns over Beach City and learns to not worry about the small details while Pearl understands Rose's goal better and becomes a bit more considerate when it comes to the people and property damage.