Heather McDonald Talks 'Blue Ball,' Jennifer Aniston's Breasts

12/15/2011 05:28 pm ET

Before hitting it big on Chelsea Handler's "Chelsea Lately," Heather McDonald was selling real estate to pay her bills. But my, how the times have changed. Now she's feeling Jennifer Aniston's breasts, hanging with her boss' ex-boyfriend 50 Cent and going to Kim Kardashian's wedding.

"50 Cent was a nice guy. Yes, it was real. He was like a mellow guy," McDonald says of Handler's romantic fling with the rapper. However, her favorite celebrity is Handler's unlikely friend Jennifer Aniston: "Chelsea did not date Jennifer Aniston but they are very similar. They are really friends and she is awesome -- I hugged her. Oh my gosh, it was everything you could imagine. She never wears a padded bra, so you always feel the hard nipple. All those years of Pilates all worked out."

Promoting her book, You'll Never Blue Ball In This Town Again, which recalls all of the nights when she didn't hook up with the guy that bought her dinner, McDonald also tells me about her experience at Kim Kardashian's wedding.

"It was fabulous, I had a wonderful time!" she told me. "I wouldn't have bet that it was going to last 30 years and they would have grandchildren. But I thought it would last a few years or something. But you know what, I didn't even get them a gift. I gave her a shower gift. I went to the shower. I got them this Mexican margarita Williams-Sonoma thing. So they liked that -- got a thank you note. Was planning on getting them a gift, but it just didn't work out."

To catch my entire interview with Heather, tune into my talk show "Naughty But Nice with Rob" Thursdays at 8:00 p.m. on HDNet.