Drew’s Age: 16
Dude: Leland Hayward, Hollywood royalty
Relationship Level: Engaged. Should anyone be engaged at age 16? Answer: no. But let’s just all forget about Drew’s stupidity at the age of 16. This doesn’t really count.
In 1991, at the age of 16, Barrymore became engaged to Leland Hayward, grandson of Hollywood producer Leland Hayward. After a few months, this engagement was called off.