The host began with his usual joking schtick, and grilled Lohan on her thieving past, violent tendencies, and upcoming rehab stay. Lohan, dressed in a white floral ensemble sans bra (of course), became increasingly uncomfortable, and started vetting Letterman’s list of jokes — which didn’t really matter because Letterman was on a roll.
Lohan called rehab ”a blessing and not a curse”, and claimed that she’s always been “a target”. After a few more uncomfortable punchlines, Letterman displayed genuine concern for the troubled star, which caused Lohan to get emotional and tear up. It was a rare sight to see Lohan being so touched, but just so, so awkward. It also begs the question: if going to rehab was so trying, why not just stop the partying, the drinking, and everything else? Seems like that would solve a few things.
Watch it go down in the video below, and shop Lindsay’s most recent court outfit: