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

2. Rita Ora

Singer Rita Ora is one cheeky lady. The 25-year-old dated Rob Kardashian for a bit, but it turns out that Rita is quite the serial dater. She also had tough breakups with Calvin Harris and Richard Hilfiger. After the tumultuous breakup with Rob, he ended up gaining about 40 pounds (and the gossip magazines and paparazzi went wild). Rob worked really hard to get himself healthy again, even though his main source of inspiration was getting with beautiful women again (not necessarily Rita). For her part, Rita is now bopping around with Justin Bieber, which just seems plain weird.