In it, Chris’ character Leo was kind of this happy go lucky maybe a bit sheltered or spoiled middle-class guy and Melissa did a guest spot as a waitress called Kelly. And Leo flirts with Kelly and they start dating and it’s kind of this controversial middle-class dates working-class story and the problems that arise from it, with him constantly wondering whether it wouldn’t just be easier to date somebody from “his class”, that she doesn’t fit in with his friends, that they don’t have the same interests or hobbies, etc. 

And on the other hand, Kelly is always sure that he’ll leave her behind eventually anyway, so there is no point in developing real feelings for him. And it was like this entire vehicle to un-obviously talk about class and gender expectations (like with this thread on whether modern middle-class men are soft and whether working-class women might be more used to “harder” men who treat them badly).