- „About 20 feet from where we're sitting right now, right. The grunion were running, it's a full moon. And that night I was lucky enough to have Kelly Taylor in my arms”
- —Steve reminiscing with Kelly at the Beach Club[src]
Steve relays to Brandon that he and Kelly dated and that he broke up with her, while Kelly tells Brenda that Steve is her ex and that he 'doesn't get the message that it's o-v-e-r'. Both are quite agitated with one another; Kelly because Steve spread rumours them, Steve because he's upset that the relationship ended.
Throughout the first season both act somewhat antagonistic, yet fiery toward one another, at times putting their friends Brenda and Brandon in awkward positions. However, over the course of their sophmore and junior year they make peace with each other and become close friends. Although Kelly is shown to care deeply about Steve, she never chooses to start up a relationship with him again, while Steve is seen multiple times wanting to be with Kelly.
It's never specified, but indicated that Steve and Kelly met when they started West Beverly in 1989. They dated their freshman year, during which Kelly's best friend at the time, Tiffany, made a pass at Steve, after which Kelly ended their friendship. After sleeping together, Steve talks about it and Kelly breaks up with him.
After breaking up, Steve spends a lot of time agonising over the break-up in private, while badmouthing Kelly in public. This is somewhat curbed by Brandon's presence in Steve's life, while Kelly is often seen annoyed with Steve, treating him as though he is beneath her, likely because of how hurt she was that he shared intimate details about their romance. In spite of this conflict, the two actually continuously flirt throughout their sophomore year, and even spend another night together. Their respective friendships with Brenda and Brandon cause them to spend a lot of time together, mostly at the Walsh house, and this has a mediating effect on their conflict.
Steve is interested in getting back together with Kelly, but mostly just teases her and she at times flirts back. When Kelly, Steve and Donna agree to stay at David Silver's grandparents home in Palm Springs, Steve decides it's time to make a direct move. He has a conversation with Kelly, where he professes his feelings for her, but she turns him down, saying she thinks they're better as friends. Despite this, Steve still carries a torch for Kelly and the two continue to spar and banter flirtatiously. Although Kelly continually hits on Brandon, Steve doesn't seem much bothered and even makes out with Andrea, which Kelly and Brandon suspect, though never confirm.
Steve does become jealous of Brandon when the Spring Dance rolls around and he asks Kelly, shocked to find that she's asked Brandon who's agreed. Brandon tries to curb the situation, but Steve gets drunk at the dance and reveals why he's angry with Kelly. He found out from his mother a year prior (on his birthday) that he was adopted and only shared the information with Kelly and he's hurt she hasn't paid any mind all night to his birthday or been a friend. Kelly and Steve talk about it and have a fight where Steve lashes out, but they both later apologise and make amends.
- Kelly – You're gonna be there, right?
- Steve – Wouldn't miss it for the world
- ―Kelly's 18th[src]
- One of the original writers and producers on the series, Charles Rosin, thinks Kelly & Steve belong together.