As for Upton, she needs someone who is comfortable with men ogling over her entire existence.
You know, someone who has been through that before.
It's been more than a decade since Diddy last dated a high profile model — a brief dalliance with Naomi Campbell back in 2002.
Following the club date, Upton and Diddy met at Gemma in the Bowery Hotel in New York on Thursday, March 28. Upton dated Detroit Tigers pitcher, Verlander, but the couple ended their relationship before Valentine's Day.
As for Diddy, he was previously linked to singer Cassie.
Diddy, who has been linked to Cameron Diaz and most recently singer Cassie, was spotted with the latter house-hunting in Beverly Hills in January.
The relationship has appeared to have since cooled off.