The drastic personality changes Dora in Questionable Content underwent during her relationship with Marten used to aggravate me, seeing as she went from being sassy and confident to insecure, clingy and almost manipulative at times. Then I realized that she had always shown hints of insecurity and indecisiveness in her personality, but it only started to show when she got to know Marten better, and trusted him enough to let her imperfections and faults become apparent.
Was this comic a subtle nod to Faye later hooking up with Sven?
Dora: Wait, you can't handle a relationship with a guy you know really well, but you'd bang a dude who has probably slept with the entire female population of Manhattan?
Jimbo the trucker writing well-selling romance novels for females? Seems unbelievable at the first glimpse. However, if you happen to be familiar with this topic, you'll know that many of these novels are essentially "emotion porn" and tend to have many scenes about women being overwhelmed by aggressive hypermasculine men. Not surprising that a redneck trucker will know better about this than a hipster Nice Guy.
In #1011, when Hannelore's dad sends her a humanoid robot to act as a practice boyfriend, Faye mentions that "you don't see fully humanoid robots running around everywhere". But in #1996, Marigold is buying such a chassis for Momo from a storefront in the local mall. But the thing is, (a) you don't — Momo is the only one we've seen on the street so far in the comic; and (b) given that in #1311 it was winter, it's probably been at least four months ... presumably long enough for a mature prototype to enter production. Not to mention they hit The Singularity in the meantime.
All the way back in #1720 Dora says that it's a coffee shop, and as long as they don't show up to work drunk or high they'll be fine. A thousand strips later, in 2879, Faye gets fired for just that.
This is more depressing than horrifying, but in this strip, when Marten and Dora break up, Marten appears to be repeating word-for-word his question from this strip - in which Dora's answer was exactly what Marten had been unable to do. It really drives home Jeph's comment that this was "a long time coming."
It indeed seemed to be a long time coming, if you analysis the contributors to the break up. One will realize that they stem from certain personality traits and personal issues (some pretty deep seated) that belong to Marten and Dora. These traits were already revealed from past humorous situations and many events which were played for laughs at the time hinted at the deep seated issues (which can now be realized in hindsight). When these traits manifested during their time together, it started to seriously damage the relationship.
At one point, Marigold does some repairs on Pintsize, after having done it before, and asks to talk to him alone to make sure that the cast isn't abusing him. The horror: These AIs only exist to ensure friendship and trust, yet they are apparently abused to the point that standard commonly-known procedures exist for it. Combine that with the fact that all the AIs want is equal rights, and it becomes a horrifying portrayal of humanity.