Random Couples You Forgot Were Engaged (20 items)

(#13) Emilio Estevez and Demi Moore

Emilio Estevez and Demi Moore broke off their engagement in 1987. Shorty after, Moore began to date her future-husband Bruce Willis.
(#3) Jennifer Lopez and Ben Affleck

In 2002, Ben Affleck proposed to Jennifer Lopez. They remained engaged for about a year before calling it quits.
(#11) Courteney Cox and Michael Keaton

Courteney Cox and Michael Keaton dated for six years from 1989 - 1995. They were even engaged for a period of time.
(#1) Winona Ryder and Johnny Depp

Winona Ryder and Johnny Depp were engaged from 1990 - 1993.
(#14) Sienna Miller and Jude Law

Sienna Miller and Jude Law were engaged in the mid-2000s, but they called things off after he was caught having an affair with his childrens' nanny. They continued to have an on-again-off-again relationship for several years.
(#10) Katie Holmes and Chris Klein

Katie Holmes and Chris Klein were engaged to each other back in 2005.