During a party where No Doubt performed in mid-1987, Stefani tried to kiss Kanal when the two went for a walk.
Kanal initially rejected her, later commenting, "It was pretty much an unspoken rule that nobody dates Gwen...almost like a bunch of brothers and our sister." He gave in, and the two began dating secretly. The band was suspicious of them, warning Kanal against dating her, but he continued the relationship.
Stefani stated that she was heavily invested in the relationship, commenting that "...all I ever did was look at Tony and pray that God would let me have a baby with him."
While the band was working on its third album Tragic Kingdom, Kanal broke up with Stefani.
Stefani later explained that he was feeling "claustrophobic" in the relationship since he did not have any previous experience being in a relationship.
She stated that the break-up "took ages" because the two were close friends and Kanal did not want to hurt her. After the break-up, he offered to leave the band, but Stefani replied that she wanted him to stay. Many of the songs on that album were written by Stefani about the breakup, most notably the hit "Don't Speak". Many years later, Stefani co-wrote her hit song "Cool" about their relationship as friends for her 2004 debut solo album Love. Angel. Music. Baby.