He gave his blessing to Triple H
The careers of Triple H and the Undertaker are intertwined, with the two scheduled to face off at WWE Super Show-Down, over 20 years after their first match.
During the late 90s/early 00s, Triple H began a relationship with Stephanie McMahon. The decision to date the boss' daughter made the Game an easily hated person, both to fans and backstage.
Seeing the Deadman as a locker room leader, Triple H reportedly asked him what he should do. According to the WWE's 2015 Attitude Era book, the Undertaker asked the future COO whether he was willing to risk everything he'd done for her. When Triple H said yes, the Undertaker said the relationship was fine and was it was Triple H and Stephanie's business, and no one else's.