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Jocelyn started with an all girl group in high school named the Pinay Divas, a reference to all girl group En Vogue who were known as the Funky Divas. Her debut album, Lovely was released in 1994 on Classified Records. The album featured two moderate chart hits with, her debut single, "I've Been Thinking About You" and "Make It Last Forever." In 1996, she moved to Tommy Boy Records, where she released her her first major hit single, "Do You Miss Me?" in late 1996 and her second album, Jocelyn in early 1997. Jocelyn peaked at #182 on the Billboard 200 albums chart and at #11 on the Billboard Top Heatseekers chart.

"Do You Miss Me?" became a Top 40 hit at dance and pop radio (#17 and #38 peaks, respectively), and peaked at #49 on the Hot 100. The single was also successful outside of the U.S. where it reached #7 in Singapore and was a Top 20 Pop hit in Canada. Its follow up, "A Little Bit Of Ecstasy" was not quite as big a radio hit, failing to cross over to the pop stations and peaking at #25 at dance radio. However, it had stronger sales than "Do You Miss Me?" (peaking at #1 on the Hot Dance Music/Maxi-Singles Sales chart, as opposed to #8), which enabled it to reach #55 on the Billboard Hot 100. "A Little Bit Of Ecstasy" is remembered to this day, due to its recent inclusion on the DDRMAX2 PlayStation 2 game. Pop punk band Lucky Boys Confusion later covered "Do You Miss Me" on their 2001 album [Throwing the Game].