I can't believe I didn't make note of this, but Clyde II (or Clyde V) doesn't tell Caroline "they're not robots." He says "you're not robots." What the what? Has she always been an Active?
I wonder if Caroline was the second or third in a series of experiments? The repetition of how Whiskey was #1 seems to be a strategic reminder that Echo has in fact taken her place, as well as the whole Alpha debacle. Before Alpha's composite event, we hear his handler assert that Whiskey is a bad influence on his guy - and at this point, Dominic has noted that Alpha is aware and dangerous, meaning that before Echo, Whiskey was the one to have gone furthest on the path to selfhood. Back in Vows, I thought Whiskey was the character through which the show was going to revisit the ideas of free will and selfhood, as much as through Caroline/Echo/cast of dozens, which maybe was a little more true to the plot than I thought at the time. Moreover, it looks like the writers determined that Boyd would be the head of Rossum between the first and second season, meaning that the decision to make Boyd ask her out in such a toolish, patronizing fashion was made after they'd fitted him in his Business Suit of Capitalist Evil. It's not a Nice Guy's misguided attempt to help her/make her think she owes him sex, it's a play to be the only person a desperate, vulnerable, and seemingly unique Active trusts, which is pretty much exactly the relationship he has with Echo. Taken with the way we know from E1 that Whiskey will end up in a broken and miserable purgatory, and while at the time she was set up like a woman waiting for her lover, she looks in retrospect like the end result of a failed experiment. Her scars bring out her eyes, sure, but they're also reminiscent of Frankenstein's monster.
I say second or third because it seems reasonable to wonder if Alpha isn't the result of this as well. It kind of seemed to me, watching the scenes of Alpha in the Dollhouse during Omega, that Alpha was quite self-aware (really, the "watch your step" gag seemed more like someone playing at being a Doll like Our Heroes did back in Needs than genuine puzzled Active behavior), enough to reasonably figure that living in a spa and being sent out once in a while for sex was better than going back to prison or worse, and it wasn't until the composite event that he gained the skills to act on his possessive, violent nature without ending up in the Attic. Moreover, if Alpha is the result of Boyd's sociopathic experimentation, it does make sense that he hasn't been tracked down and killed - Rossum HQ could have said he was their problem now, and Adelle and Dom certainly wouldn't have begged to get that responsibility back - and we know why Boyd didn't shoot Alpha when he could have back in 2.8. The game wasn't over.
Boyd, what with his total facade identity and endless sexual exploitation, is kind of like Don Draper. OF THE FUTURE.