I have a really hard time understanding the connotation of the
term「まじめじゃない」or「まじめな人」, I know the denotation is "a serious person".

Phrases like「まじめに仕事する人 (A person who works hard/takes their job seriously)」are
easy to understand, but when it comes to the other 2 phrases they seem
subjective, where the connotative meaning is in the eye of the beholder.

Like, most girls in Japan say「まじめな人がいい」but ask them what their definition of
a「まじめな人」is and you'll probably get varying answers.

Just going by the denotation I "think" I would qualify as a「まじめな人」and
sometimes I'm told「まじめだね」, but mentioning this to my girl and I get a reply
of「お前まじめじゃねぇ」, and I want to yell "WHAT IS A「まじめな人」THEN?" lol

It seems everyone has a different notion of what they perceive to be
a「まじめな人」or「まじめじゃない人」。
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meaning connotation
Are「まじめじゃない」、「まじめな人」subjective terms
I think the definition of 「まじめな人」is a person whose way of life is faithful in
the light of your sense of values. Because the sense of values of life varies
in each person, the definition of 「まじめな人」will be so.

* * *

What is your connotation of a 美人｛びじん｝`beauty`? It may be in the eye of the
beholder, as is said 「蓼食｛たでく｝う虫｛むし｝も好｛す｝き好｛ず｝き」, and so is the word 「まじめな人」.

* * *

  * There is no accounting for taste.

  * Not two people have the same likes and dislikes, or do things in the same way, so it is a waste of time to argue about it. 

  * Beauty is in the eyes of the beholder.（美｛び｝は見｛み｝つめる人｛ひと｝の目｛め｝の中｛なか｝にある。）

  * Every man to his taste.（全｛すべ｝ての人｛ひと｝にそれぞれの好｛この｝みがある。）

  * One's man's meat is another man's poison.（ある人｛ひと｝の肉｛にく｝は別｛べつ｝の人｛ひと｝の毒｛どく｝。）

  * There is no disputing about tastes. (人｛ひと｝の好｛この｝みは論議｛ぎろん｝できない。)

  * So many men, so many opinions.（たくさんの人がいれば意見｛いけん｝も様々｛さまざま｝だ。）
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I would say that まじめ includes the ideas of being responsible, doing your best,
being serious-minded, well-intentioned, well-meaning, etc, often with the
implication of being more serious-minded, responsible, etc, than the situation
demands and that you may be acting against your own interests. Consider the
expression バカまじめ、 "well-meaning to an unreasonable degree". The Japanese Post
Office ran (is still running?) a series of ads for the ゆうパック delivery service
which shows staff members doing things like running a considerable distance
through city streets and up a huge flight of steps to ensure that a package is
delivered to someone who has just moved from the place to which it was
addressed. The slogan was 「バカまじめ」 . In the 1960s there was a TV series called
まじめ人間 (starring the great actor Nakado Hiroyuki 長門裕之), which was about the ups
and downs in the life of a lower-middle-class salaryman doing his best in the
face of the difficulties that faced him. The jaunty theme-song included the
line 「まじめ人間、バカ人間」.
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