The 10 hottest women Rob Kardashian has slept with (With Pictures)

9. Angela Simmons

Angela and her sister Vanessa were hot commodities a few years ago when they unleashed their designer shoe brand called Pastry. Though now we barely hear anything about them in the news. But in March 2010, Angela Simmons had an alleged hook up with Rob Kardashian (…Woo?). This rumor has been floating around for years now, and most people have pretty much assumed that Angela and Rob had a one-night fling. Rob must miss 2010, back when he was single and definitely ready to mingle! Angela announced that she was pregnant with her first child in late spring 2016.