Based on available information, it appears Leonardo DiCaprio is frequently cited as a celebrity with an extensive dating history.
While it's difficult to definitively quantify "the most," DiCaprio has been publicly linked to numerous models and actresses over the years, solidifying this perception. The provided reference suggests "more than 20 stunning models and talented actresses." Without precise figures for other celebrities' dating histories, a direct comparison is impossible. Public perception and media coverage largely contribute to this designation.
It's important to note that public perception of a celebrity's dating history is influenced by media attention and may not reflect the complete or accurate picture. Further, what constitutes "dating history" can be subjective.
