Charlie Sheen goes on a "private adult vacation" with a porn star, a stoner sex kitten, and his ex. Lindsay Lohan considers a plea deal requiring six months of jail time. Hugh Hefner sets a date for his wedding to a 24-year-old. Thursday gossip harshes the mellow.

Charlie Sheen's mysterious new girlfriend—the one he sucked face with for an audience of thrilled paparazzi—has been identified! Meet Natalie Kenly, "Natty Baby," marijuana bikini model. (Until now, I was not aware that genre of bikini models existed, but it makes sense. High Times is page after page of high-def bud porn, anyway.) Claim to fame: Posing in a Girl Scout vest, panties, and a strategically placed bong for Cali Chronic X magazine. My gut reaction is that this choice in woman is good: If she's a stoner, she's probably not a crackhead, right? Charlie, Natty Baby, porn star Bree Olson, and battered ex-wife Brooke Mueller are all on a "private adult vacation" in the Bahamas. Together. Big Love meets Eyes Wide Shut meets Harold & Kumar Go to a Sex Colony in the Bahamas? [TMZ, TMZ, images via Cali Chronic X's Photobucket and Getty]

  • After Lindsay Lohan's judge said he'd only consider a plea bargain that included jail time, the D.A. offered LiLo a deal that would include six months in jail. Even if she miraculously pulls off a deal with minimal jail time (TMZ thinks she'll plead "no contest" and hope the judge gives her a softer sentence) she'll probably have to serve time for violating her probation, anyway. [TMZ]
  • Meanwhile, LiLo is "telling friends" she totally didn't mean to look slutty at court, again, it's just that her boobs keep jumping out of her outfits. She could be wearing a burqa, and there would be cleavage. [TMZ]
  • Last LiLo item: Apparently the contents of the fabled surveillance tape shows Lindsay trying on the necklace while a male acquaintances "distracts" store clerk, then LiLo walks out with the necklace on. [Radar]
  • Lady Gaga met Liza Minnelli backstage at Madison Square Garden, prompting a thousand theatrical gay minds to explode all at once, raining glitter and stardust all across the land, like that one scene in Glitter where Mariah Carey turns out to be a pipe bomb packed with glitter. (Yes, I know I made a Glitter reference last week, too. I really like that movie, OK?) [BroadwayWorld]
  • 84-year-old Hugh Hefner and 24-year-old child-bride-to-be Crystal Harris set their wedding date: June 18, in the Playboy Mansion, with the lead pipe and Professor Plum. [Us]
  • Amber Portwood, the Teen Mom facing domestic violence charges who has a picture of her daughter tattooed on her belly, is having a naked picture scandal. Everything about that sentence is terribly, horribly disturbing, but the good news is she's not a teenager anymore, so you won't go to jail if you click the link. You might, however, go to hell. [Egotastic]
  • Jason 'Gummi Bear' Davis—smack addict oil heir, Celebrity Rehab fameball, and Paris Hilton bosom buddy—has been charged with felony heroin possession in Orange County. He faces up to three years in prison if convicted. [TMZ]
  • Upon cutting Jennifer Aniston's hair into a bob, celebrity hairstylist Chris McMillan announced that big hair is over: "There are so many long, layered hairstyles, and—don't get me wrong, I love that—but The Real Housewives of Beverly Hills all have that." Camille Grammer, consider your appointment at McMillan's salon canceled. [Allure]
  • Psycho figure skater you totally forgot even existed until now Tonya Harding had her baby. Boy. [Oregonian]
  • Dear god this is embarrassing: Two New York state senators are dating, and we're supposed to refer to them as "Albany's Brangelina." That is the complimentary metaphor ever made about a random pair of state politicians. Good job, "Klavino," blended moniker for Jeffrey Klein and Diane Savino. [P6]