Is Lance Armstrong just a shiny red sports car (with bike rack, natch) away from a full-blown and slightly early midlife crisis? The seven-time Tour de France champ, 36, has apparently pedaled directly into the pouty lips of 21-year-old Ashley Olsen. (Go on, say it, we'll wait: Ew.) The squicky twosome -- the teensy, fashion-forward twin is closer in age to Armstrong's 8-year-old son than she is to him -- turned up Monday night at Manhattan hot spot Rose Bar, where a spy snitches to the New York Post, "They came together with a group of friends. Ashley drank red wine, sat on his lap and they were making out all night. They left together around 2 a.m." The New York Daily News also caught them "nuzzling up" that night, with an eyewitness recalling, "Ashley and Lance settled in and within minutes, he was whispering in her ear and she was giggling like a schoolgirl. They totally looked like they were on a date." Armstrong recently ended his romance with designer Tory Burch, while older guy-preferring Olsen has dated Tsubi jeans exec Greg Chait, club owner Scott Sartiano and Jared Leto.

Despite some recent paparazzi-documented smoochies, Pink and Carey Hart can't seem to escape tabloid talk that their 2-year-old marriage is teetering on the edge of collapse. The latest prediction of doom comes from Life & Style (via Perez Hilton), which says they've both been spied acting flirty in the last couple of weeks. The cheeky popster purportedly sidled up to a "gal pal" at a Los Angeles hotel (not so, says her rep), while the motocross champ was supposedly spotted dancing and "having a great time" with a brunette at a Miami club (nuh-uh, reiterates Pink's flack).

Reese Witherspoon and Jake Gyllenhaal attend the "Rendition" photo call during the Rome Film Festival on Oct. 21. (Omega/Capital Pictures/Retna Ltd.)

Reese Witherspoon and Jake Gyllenhaal have rapidly gone from wily to smiley. On the heels of their touchy-feely, piggy back-ride-capped tour of Rome, the once clandestine couple was caught on video a few days back yukking it up on a Los Angeles beach. Alas, Gyllenspoon's physical interactions mainly consisted of the Oscar-winning mother of two wiping schmutz off the actor's bristly, be-bearded face and gently rubbing his back. No word on whether she got him to burp.

Will Diddy soon find himself on the wrong end of Kid Rock's well-documented jealous streak? The New York Daily News says the ladies' man music mogul spent some time at the Angel Ball Monday night getting to know Danish looker May Andersen, the most recent squeeze of the stringy-haired, fisticuff-prone rocker. "He kept his arm around the model for most of the evening -- whispering into her ear," an eyewitness tattles to the paper. Diddy and May reportedly exited the fete together.

And finally, in a bit of vintage romance news, did Madonna once have a dalliance with Tupac Shakur? The New York Daily News reports a new book on the pop queen delves into her brief encounter with the rap star, which allegedly took place about a year before he was gunned down. "She was going out with him," a friend of the Big M recalls in the bio, "but homegirls were saying to him, 'I can't believe you're going out with a white girl.'" Madonna was apparently soon given the heave-ho.

Next: Womb Watch: Nicole's Nic Fit, Cavalli Outs J.Lo