I'm absolutely reading too much into these comics, but I feel like there's something very profound here. Pintsize has built up this identity as a sexual pervert, his whole shtick is shock value. We aren't shown the actual asking process that lead to these events, but do you think Pintsize expected May to agree? Now that he gets what he asked for, he finds out it isn't what he wanted. His identity was built around something that he did not actually feel. You can even go back and look at #2332 and do a whole rereading of the QC archives where Pintsize curated this identity out of boredom or spite while he was Marten's only friend. His giving free money to Faye in #430 is motivated by an unconscious but enormous gratitude for someone else to talk to.
Just to restate - he is canonically Marten's only friend for TWO YEARS. That is 730 days! I like my friends and suitemates and etc, but I can't think of anyone I would want to hang out with daily for two whole years without anyone else ever being involved. Like, after a while you run out of House reruns to watch and you've told each other all the puns you know. And Marten sucks! First thing he does when he comes home is complain about his job, and he doesn't even know what HIS CLOSEST FRIEND does when he's not around. Pintsize has to put up with this lame asshole for 17,520 hours!
This idea also fits perfectly with the interpretation of the comic that says Marten's mom is a The Wall-esque overbearing and controlling figure that made him grow up into such a loser. Eventually all the pieces will come together and it will turn out that Jeph accidentally wrote a modern Shakespearean tragedy.