Leonardo DiCaprio has had a string of high-profile relationships with stunning models under the age of 25, but has he finally found the one? He is currently dating Italian model Vittoria Ceretti, and there have been rumors of an engagement after she was spotted with a heart-shaped diamond ring on her wedding finger. However, recent reports suggest that Leo spent an evening with singer Teyana Taylor, causing some controversy. Despite this, Leo and Vittoria have put on a united front and were seen together at a Halloween party. This article takes a look at all the loves throughout Leo's life as he celebrates his 50th birthday.