I already did, and the answer was "Yes, I'd be okay" (although the likelihood of that happening is extremely rare).
> Ever googled something embarrassing?
Use incognito mode.
> Perhaps a medical condition or symptom?
I have only one medical condition, which I'm not embarassed to talk about publicly (I already do it).
> Sent a very personal email?
I rarely send "very personal"/ intimate information over email in lieu of just talking over phone.
> Visited a less than savory location,
Never in my life.
> or lied to an employer about your whereabouts?
I never had to do it (why would I?).
> I’d be willing to bet most people have some data that could be weaponized for blackmail.
If--note "if"--I were to engage in an activity that could potentially be used to blackmail or harm me in any way, I would of course be doing it in as private manner as possible. However it would be silly to spend the rest of my normal life cowering and being phobic to technological advances.
> Surely many people (especially the ignorant) will find Google’s products and services “worth using” but privacy concerns are anything but overblown.
You confuse being naive (in its original sense of the word) with being ignorant. But I guess that's what fear does to one.