Chris Jericho
Stephanie McMahon and Chris Jericho have definitely built one of the best alliances which also later turned into an entertaining feud. In the early 2000s, Jericho roasted Stephanie on-screen in a non-PG way while addressing her breast surgery on live TV. On the August 6, 2001, episode of Monday Night Raw, Y2J smashed a pie on her face. Later, Jericho competed against Rhyno on that night, won that match, and planted a big kiss on Stephanie’s lips, to leave him in anger.
Eric Bischoff
WWE often played random romantic angles or makeout sessions on TV without any proper reason. Eric Bischoff kissing Stephanie McMahon was one of those instances. At that point, the two were acting as General Managers of Raw and SmackDown, respectively. On the Halloween 2002 episode, Steph went to check on his dad’s office only to find out Eric was waiting for him. The former WCW owner grabbed her forcefully and enjoyed a quick smooching session by lying on the office desk. Interestingly, never again on WWE TV, this segment was ever mentioned.