Second Time's the Harm?

Sarah Silverman, Jimmy Kimmel Michael Owen Bake/ZumaPress

Their friends are cautious. Their reps are mum. Maybe that's because all folks involved know that what Sarah Silverman and Jimmy Kimmel are attempting is unlikely to work out? "They're being very careful," says a mutual bud to both comics, who have made no secret of sniffing around each other in recent days, in hopes of giving it another love try.

And isn't it interesting that the busted-up couple S.S. just likened herself to on The View, Bruce and Demi, are a just-friends twosome, with no nooky whatsoever involved, not exactly the scenario we hear Sarah 'n' Jimmy are currently entertaining. We'd be circumspect too, babes, with breakup/hookup/breakup-damaged duos such as the following littering H'wood's Cupid catastrophes:

Liz and Dick—sex was great, fights and booze and drugs were even greater.

Shanna Moakler and Travis Barker—might be back on now, thanks to an incredibly dire circumstance.

Sienna Miller and Jude Law—completely off, despite numerous attempts at reconciliation.

Pam Anderson and Tommy Lee—will be back on one day, yet again (and again, until something wicked befalls one or either party, to be sure).

Lance Armstrong and Sheryl Crowshe better not take him back, 'cause Southern heavens knows he'll be asking. Again. Prolly right around the time he decides to run for office.

Dubya and Laura Bush—even though the first lady moved back into the presidential digs after a trial time apart, the real test will be post-White House. Stay tuned, babes, ain't gonna be pretty.

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Truth, Lies & Ted

  • Truth, Lies & Ted, Nov. 26

    Ted gives thanks for Mariah and Nick's matrimony, Madonna's marriage meltdown, Obama's victory and more!

  • Truth, Lies & Ted, Nov. 20

    Is Nicole and Keith's romance really a fairytale? Does Katie Holmes keep in touch with her ex? Get the gossipy scoop.

  • Truth, Lies & Ted, Nov. 13

    What's "Twilight" hottie Rob Pattinson's audition tradition? Is Hef charging his "Girls" rent? Get Ted's hot scoop!

  • Truth, Lies & Ted, Nov. 6

    Who's talking trash about Jake Gyllenhaal? Is Joaquin Phoenix pulling a publicity stunt? Plus, Groban gets desperate, more.