During a November 2002 interview with Diane Sawyer, Jennifer announced her engagement to Ben and showed off her new 6-carat pink diamond ring. When asked about the proposal, J Lo told Diane it was "traditional, but also in a very spectacular way, as of course Ben would do it . . . It was very, very beautiful." She also gushed to Diane about her and Ben's similar upbringings and revealed how Ben won over her mother.
Right around the same time, the music video for "Jenny from the Block" made its debut on TRL. The video prominently featured Ben in several raunchy scenes, and though it delighted fans, Ben later admitted he regretted the move. "If I have a regret, it was doing the ['Jenny from the Block'] music video," he told Daily Record in 2008. "But that happened years ago. I've moved on."