People like Bob live by that one quote in "A Million Ways To Die In The West":
"If two people hate the same thing, it creates a bond. Hate can move mountains."
Normal people will connect over things they like. People like bob see people who hate some of the same things as he does and assume this makes them kindred spirits.
The problem is, especially where Bob's Breadtube senpais are concerned, they do NOT hate *exactly* all the same things. While they might concur with Bob in hating the bad, bad Orange Man, this in itself is insufficient. Bob hates the White Working Class, which Breadtube does not hate, as the White Working Class is an integral part of the underlying philosophy of Workers Of The World Unite. Hell, Bob seems completely ignorant of the fact that there's an entire concept of trying to unite the white working class with all the other colors of working class because the Elites back in the day used race to keep the Whites from helping the Blacks (over slavery, Jim Crow stuff, etc) and everybody else (Chinese, Native American, whatever else), and they're trying their damnest to undo all that damage and Kino Roberto doesn't comprehend its importance and is actively working against it/to sabotage it.
But yeah, this is probably why he hasn't much luck with women (aside the alleged one night stands most likely with a woman with severe beer goggles and the Lesbun "beard" thing) - he's trying too hard to find a woman that hates the Mayonnaise Ghouls with the same fury of a thousand suns that he does. Nothing else/no-one else will do. Most women who aren't complete sociopaths would take one listen of Bobbenfuehrer's Final Solution for the Wasteland Children of the Mayonnaise Corn and go "That's a big yikes from me, dawg" and nope the fuck out.