Throughout most of Adventure 02 Daisuke shows a comically exaggerated crush on Hikari. Because of her closeness to Takeru this often puts him at odds with the other boy who Daisuke sees as a rival for her affections. Daisuke knew her before the start of Adventure 02. Daisuke is very distressed when Hikari is trapped in Andromon's city in episode 7.
In episode 22 Daisuke gets V-mon to evolve into XV-mon in an attempt to impress Hikari. In episode 45 when Ken is trying to open the Dark Gate and Daisuke is telling him not to give up and that he is not the Digimon Kaiser anymore Hikari thinks "This warmth...is it from Daisuke's heart?".
In the Door to Summer drama CD Daisuke becomes depressed when Hikari turns down is invitation to the beach. In the Diablomon Strikes Back movie Daisuke hears that Hikari has gone onto the internet and almost abandons his task of collecting the Kuramon to help her until Ken reminds him of his task. Later on he decides to go into the internet again and begs a laptop off of a stranger, but the fight with Diablomon would end and the rest of the Kuramon would go to the real world before he got the chance.
Daikari is one of the most popular shippings, but nowhere near as much as it's rival Takari. Many fans found Daisuke humorous attempts at courting Hikari made them a good couple while others found it annoying. The relationship also appears to be entirely one-sided as there is not really any evidence from Hikari's side.