7. VANESSA MINNILLO
When: May 2005
When TRL was still a thing, Bloom appeared on the music video countdown show while Minnillo was still a host. Shortly after his appearance, they were allegedly spotted kissing and dirty dancing in a New York club. They also suspiciously left alone within a few minutes of each other.
Smash Probability: Their super secretiveness suggests that they hooked up at least once.