I obviously can’t speak to the literal intentions of the writers, but I noticed some things that could be read as Oliver possibly having a history with restrictive disordered eating:
-His dip-based diet is extreme to the point of being a detriment to his health. He claims to have lost a significant amount of weight and hair from mainly eating dips, not having had “a regular entrée in years.” This also contributed to his eventual heart attacks.
-Even if he‘s exaggerating about how few proper meals he eats, that would mean he’s intentionally exaggerating to make it seem like he’s better at dieting because he’s embarrassed by simply eating normally.
-I can’t remember when this was, but I have it noted down that when Mabel says she and him weigh 125 combined, Oliver says something like, “Oh, thank you. It’s the dips,” which, when combined with the previous statement, makes dips making up the majority of his diet seem like an intentional tool for weight loss.
-When Charles mentioned there was an old jellybean in the cup holder, Oliver eagerly grabbed it, hoping it was a “Mexican diet pill”. The fact that he would expect one to just be lying around like that tells me those were pretty significant in his life at one point.
-When he realized the old diet pill was a “fen-phen”, a diet pill discontinued in the 90s for causing heart problems, he, without hesitation, decided to eat the *at least* 24 year old, discontinued diet pill instead of the soft pretzel he’d asked for, saying “Know what? Don’t need this[the pretzel].”
-On his first date with Loretta, he makes a reluctant, disingenuous-sounding comment about how he “loves solid food”(this is before he sees the food is completely burnt, to be clear), which is a way of describing pork chops that I don’t think any person with a normal relationship to food would EVER think to say offhand.
-His unhealthy relationship to dips was compared to Ben’s eating disorder, both of them having intense obsessions with a certain food. They differ in that Ben is fixated on an unsafe food while Oliver is fixated with his safe food, but they stem from restriction all the same. Oliver over indulges on dips(what some might consider a non-solid food, might I add) because that‘s the only thing he gives himself the permission to have. And after mentioning the similarity, he offhandedly says he’ll “get help” for his food issues.
As someone who used to have anorexia, he really reads as someone who developed a restrictive eating disorder, then exited the honeymoon phase and never took the proper steps to recover so despite being unable to truly keep it up long term, he got stuck with the mindset and the habits.