Dork-O and his Mutant Orange Date

Dear Sister,

I'm not sure what's going on here. Is Jessica Biel trying to match her skin to her dress? Has she done something to her face? Is Justin worried about wearing his contacts too late at night? And which one is the girl in the relationship again?

Oh Dear Sister, your question are painfully difficult to answer, but I'll try my best. In order of their being asked...

Yes.
Yes (see above).
No - clearly those are x-ray glasses a la Mission Impossible.
Wow - that's a tossup. Judging from her biceps and his overly moisturized skin, I'll have to go with...

Oooh! Shiiiineeeee...

My Little Pony

SJP is so cute when she tries hard. Hence, these shoes:

Dear Sister, to this trend I say both "nay" and "neigh."

Oh Dear Sister, I see your bad pun and raise you a haiku:

Sarah Jessica
Why the leather cloven hoof?
Quit horsing around

Tiny Tim...er Tom

Dear Sister: Whilst browsing People early this morning, I came across this picture, and my first thought was - has Tom shrunk? I mean based on this picture...

Yes, Dear Sister, he has apparently left the lifts at home this time. More pressing, though, is the constant matching of these two. To wit:

The "Boyfriend Jeans"

The "Awkward Hand-Holding Ill-Fitting Blazers"

and, the "I Can't Believe They're So Identical Looking Suits"

Call me crazy, but I can't help but think that this is the next logical step: