If the walls of the penthouse suite of Chicago's Peninsula Hotel could talk, what a story they'd tell. The Chicago Sun-Times reports Brad Pitt and Angelina Jolie are currently crashing in the $7,500-a-night, 3,000-square-foot ultra-deluxe pad, which just happens to be the exact same place where Jennifer Aniston stayed -- and was snapped in a balcony-set smooch session with Vince Vaughn -- while filming "The Break-Up" in 2005. As the paper ookily points out, Brangelina may even be laying their pretty, complementary-highlighted heads down on the very $20,000 Hastens bed where Vaughniston once slept. As for the tabloid-plagued amours, who are in the Windy City for a couple weeks while Jolie finishes shooting the thriller "Wanted," they are "totally low maintenance and keep completely to themselves," says a snitch. Perhaps it's because they have a serious support system in place for tots Maddox, 6, Pax, 3, Zahara, 2, and Shiloh, 14 months. The world's most famous blended brood reportedly arrived with an entourage a half-dozen strong, including bodyguards and various assistants.

Meanwhile, in other hotel news, did Reese Witherspoon recently mix business with pleasure? Us Weekly reports the Oscar-winning mother of two had a "secret hotel rendezvous" with rumored-to-be-rekindled honey Jake Gyllenhaal while stumping for her new Avon deal on Aug. 1 in Los Angeles. Reese supposedly "stashed" the dreamy-eyed actor in a "secret guest suite" set aside for her at the Regent Beverly Wilshire. In between talking up the wonders of Avon products to the press, the comely actress joined Jake for a cozy lunch, according to the mag, which says they later holed up for the evening at his Hollywood Hills digs. "Reese doesn't have Jake spend the night when the kids are around," explains an insider. The pretty pair's continued together-time will likely further quell rumblings that Witherspoon could be considering a reconciliation with almost-ex-husband Ryan Phillippe (they share custody of tykes Ava, 7, and Deacon, 3), a scenario her pals scoff at. "If any of her friends thought for a second that she was considering getting back together with that a**hole," one source rants to the mag, "they would all set up camp at her house to stop her!"

Does Bruce Willis prefer to woo women who have already received the Hugh Hefner seal of approval? Just two months after the smooth-pated star, 52, was linked to 23-year-old Playboy Playmate Tamara Witmer, he's apparently upgraded to a Playmate of the Year (circa 1998). TMZ.com reports Bruce has been snuggling up to pneumatic former centerfold Karen McDougal, 36, during a yachting sojourn in Sardinia, where the well-toned squeezes were snapped cavorting in the sea. But the actor's rep takes pains to point out that the pairing is nothing serious. "Karen is just someone he is going out with," the spokesman pooh-poohs to FOX News. "Bruce goes out with a lot of different girls." So, just what does McDougal look for in a man, besides the ability to check her reflection on his noodle? According to her Playboy profile, her turn-ons include blue eyes and bubble butts. Her turn-offs are negativity and "people who think they are 'players.'"

Speaking of turn-ons, Terrence Howard has some very specific ideas about his perfect partner. "I like women who look like me," he informs Elle. "Generally, you're attracted to women who look like you, because the most beautiful thing in nature is your own reflection." Oh-kaaaaay. The actor also declares his opposition to premarital nookie, although he fesses up a few women have "pushed for sex, and sometimes they won. Afterward, I would feel -- unclean, like I'd compromised my own values. So I would have to let them go because they didn't help me be a stronger person." Cleanliness is a running theme for Howard, who tells the mag that a sure sign of romantic incompatibility would be -- *warning* major TMI ahead -- if there were no baby wipes, only toilet paper, in a woman's bathroom. "If they're using dry paper, they aren't washing all of themselves. It's just unclean," he pronounces. "So if I go inside a woman's house and see the toilet paper there, I'll explain this." It would seem Terrence's ideal inamorata is one who brings her own bidet to the relationship.

It may be the dog days of summer, but the Hamptons are probably feeling awfully chilly right about now. The New York Daily News reports contentious exes Paul McCartney and Heather Mills are both spending time at the popular summer destination, supposedly to do a bit of surreptitious "family bonding" for the benefit of their 3-year-old daughter, Beatrice. The presence of the bitter former flames has created a logistical headache for local hot spots. "We were expecting Paul last weekend, although he didn't show," a promoter tells the paper. "But we were specifically keeping Heather off the guest list in case he came. There is no way those two can be in the same place in public."

Next: Kate on Monogamy, 'Primal' Men & Mammaries