Someone Else's Obsession
Elaine and Guybrush never did get their first date due to LeChuck kidnapping her. LeChuck had been obsessed with Elaine since she was a child, wanting her hand in marriage when she was only seven years old. An obsession that had never faded, it cost her parents their lives, her grandfather his memories, all that to protect her from LeChuck.
Elaine almost lost Guybrush on several occasions because of LeChuck's schemes. Guybrush, despite knowing he was in constant danger from LeChuck because of his relationship with her had stood by her and protected her, even when they didn't know each other well.