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The word "tomboy" is used to express the idea of a girl who behaves in a boyish manner. It's not usually considered a negative term, or at least not very negative, and generally just means the girl enjoys more athletic activities and doesn't concern themselves with acting very 'feminine'.

On the other hand, the nearest term I can think of for the reverse idea, of a boy who takes pleasure in more feminine activities, and who doesn't concern themselves with manliness, is "dandy" (like a fine dandy boy), which carries some negative connotation that I wish to avoid.

Is there a better, less negative term that refers to a boy who acts in a feminine manner, or who enjoys activities that are more female-oriented?

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    Sensitive, empathic, careful, quiet, bookish, articulate, compassionate, particular, gentle, delightful, well-mannered, well-spoken, charming.
    – tchrist
    Commented Dec 8, 2013 at 16:06
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    On what basis do you say that dandy carries negative connotations? I ask because I am not aware of such, if there is, and indeed Wikipedia has a list of famous dandies, which does not seem pejorative at all. Commented Dec 8, 2013 at 16:08
  • @alkenrinnstet It's definitely a more modern negative connotation.
    – Zibbobz
    Commented Dec 8, 2013 at 16:28
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    @tchrist I don't really see why any of those words should not also imply masculinity. What was a gentleman meant to be if not a gentle man? On these gender issues there is a disconnect between America and the UK, largely, in my view, due to the fact that more changed, I suspect, in Britain in the post-Pankhurst era than was the case in America. Margaret Thatcher won power not on the back of modern feminism, but on the back of the early twentieth-century movement. Indeed someone observed that she did for women in politics what the Boston strangler did for door-to-door salesmen.
    – WS2
    Commented Dec 8, 2013 at 19:17
  • I would vote for "dandy" -- it probably carries fewer negative connotations (at least fewer homosexual connotations) than any alternative.
    – Hot Licks
    Commented Apr 4, 2015 at 22:18

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Language Locks

The key problem with finding such a word is that our entire culture and language is set up to view masculine traits positively and feminine traits negatively. It’s just as built-in as thinking of left being something sinister (like a left-handed compliment) and right as something that is good and proper (like righteousness and human rights).

Don’t believe me that it’s hardwired into our entire language? Countless examples exist. One cannot speak of being virtuous or having virtues, let alone of virility, without ultimately tracing back to vir, the Latin word for a man.

Another would be the way that the majority of English poetry employs something that has come to be called masculine rhyme, with a final strong syllable rhyming at the end — in opposition to feminine rhyme, where the final syllable or syllables are unstressed: weak.

So while it is seen as socially acceptable, indeed at time even even desirable, to ascribe to a woman various stereotypically masculine traits in a positive way that makes us view her positively, it is exceedingly difficult to ascribe to a man any stereotypically feminine trait in a way that does not seem to put him down.

It’s exceedingly difficult to break out of this lock on language, culture, and connotation. Even the original poster’s tomboy is a compound word formed of two words that both mean something male — a tom and a boy — yet we now use them together on a female without denigrating her. It doesn’t work the other way around. If the opposite of boy is girl and the opposite of Tom is — well, just pick any girl’s name you please, like perhaps Nell — you’ll find that calling a lad a nellygirl is certain to be taken as an insult.

The locks aren’t just on language, either. It’s on hair, too. Notice how a short-haired woman is considered butch, while a man with long locks is often considered if not exactly effeminate, at least part of the counterculture not the professional one.

Enter the metrosexual

Existing words like androgynous or epicene don’t really work, because they partake too much of an undecided, decadent, or even sybaritic nature, all of which are considered undesirable.

We do have one neologism of recent coinage, though, that takes a stab at doing just this very thing: that word is metrosexual.

It was invented mostly for marketing purposes, so I’m far from completely certain of the word’s real success in creating such a word with positive affect, nor of its ultimate fate as a word that endures outside the muddled mumblespeak of marketeers’ prattle. But it does now exist, at least for a while.

I do wish there were something better than this; see my initial comment to the OP’s question. Good luck on your quest.

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    I believe tomboy used to be quite derogatory, but that was at least a century ago. From Google books ca. 1887: "A tomboy, the neighbors said, as they uplifted hands and eyes in righteous horror at each new prank and fresh wild freak of this winsome little fairy. No, not a tomboy. Only a child, …" That quote makes me wonder whether there was any association of tomboy with lesbianism at the time. Commented Dec 8, 2013 at 17:50
  • I'm fully willing to accept Metrosexual as an answer. And your explanation is fantastic. Very, very well done.
    – Zibbobz
    Commented Dec 9, 2013 at 3:35
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    'Metrosexual' doesn't really imply the dancing-rather-than-treeclimbing, toy-prams-rather-than-battle-axes opposite of the archetypal teenage tomboy, though. Commented Jan 31 at 14:35
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    Metrosexual refers specifically to (heterosexual) men who take an interest in their appearance and use beauty products, hair products, fragrances, etc; the comparison is to homosexual men rather than women. It's also normally used of adult men rather than children. So not very like tomboy, as Edwin Ashworth has already said, although it's hard to get much closer. The alternative would be something horrible like "sissy" or (as in the Beano) "softie".
    – Stuart F
    Commented Feb 1 at 9:56
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The best word that I could image in the word "effeminate." Merriam-Webster defines it as "having feminine qualities untypical of a man" which seems to have exactly the connotation you are referring to. This term is rather derogatory, however, so it may not be perfectly comparable to the term "tomboy." The other definition for effeminate shows the gender bias, this time in the opposite direction, at work. Merriam-Webster also describes effeminate as "marked by an unbecoming delicacy or over-refinement."

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Varying in specifics and how "loaded" some are:

  • twink (an effeminate, gay teen, mostly neutral/positive)
  • girlyboy (effeminate young, between neutral and negative)
  • sissy, pansy (effeminate/weakling, definitely derogatory)
  • trap (androgynous to the point of likely confused with female, often crossdressing, usually gay, neutral/positive/humorous)
  • ladyboy (same as trap, but connotations may lean towards negative.)
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    I wouldn’t say twinks are necessarily effeminate, though they’re definitely not stereotypically macho, either. ‘Boyish’ is probably a more apt description. Commented Dec 8, 2013 at 19:14
  • @JanusBahsJacquet Wikipedia says “Twinks are often clean-shaven to emphasize a youthful, fresh-faced appearance.” The term may be used disparagingly by those of a more ursine or gerontophilic bents, but certainly is a positive when uttered from the mouths of ephebophiles. It’s a bit odd that there is even a name for this, given the ancient notion that the flower of youth occurs between the ages of 16–21 maybe ± a year or so, and this largely irrespective of gender or orientation.
    – tchrist
    Commented Dec 8, 2013 at 19:45
  • Twink is maybe positive in terms of looks, but typically (like bimbo) often implies pretty-but-stupid. And I certainly wouldn't use it as a compliment outside specific queer circles.
    – Stuart F
    Commented Feb 1 at 9:59
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I want to say Femboy, simply because that would make sense. I've been trying to push the idea that Femboy is not a sexuality but a style and personality. That one can even oppose modern day progressive movements and still be a Femboy.

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  • While I appreciate your feelings on the matter, like many other suggestions on this question you can't eliminate the unwanted connotation just by wishing for it to be so. Language is a shared form of communication built by agreed upon meanings - if no one else agrees with you on the meaning of a word, the only one speaking that language is yourself.
    – Zibbobz
    Commented Jan 31 at 19:53
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Girlyboy is not universally seen as a negative.

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    Sure it is, just like ladyboy is.
    – tchrist
    Commented Dec 8, 2013 at 16:46
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    @tchrist, while I cannot conceive of anyone using the term ‘girlyboy’ (or ‘girly boy’) without at least some measure of derogation, ‘ladyboy’ to me carries no such negative connotations. ‘Ladyboy’ is a specific thing, and it has nearly always been every bit as neutral as ‘mime’ or ‘Harlequin’ when I’ve heard it used. Commented Dec 8, 2013 at 19:12
  • Ladyboy refers to a trans woman and considered offensive by many trans people (it is different to a boy who has stereotypically feminine interests). Girlyboy is not a widely used term, but I can't imagine it being considered complimentary by most men.
    – Stuart F
    Commented Feb 1 at 10:01
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What about fairy?

I am kidding, of course. I don't think there is any neutral, non-sexual term to refer to boys that enjoy behaving in a more girl-like manner. The closest I can think of is nancy boy, but that's not exactly neutral.

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    In the 1960s, when men's long hair first became fashionable, some made a point of going to a ladies' hairdresser and merging their sexual identity, with men's bright and colourful clothes for the first time. This was the era of Carnaby street. The Beatles were in the vanguard of this idea. Cissiehood as a concept was in decline, but like a lot of things of the sixties, that unisex idea was lost in subsequent decades. This is only a personal recollection. It would be interesting to hear the views of a social historian on the matter. But critically I don't remember a word for it.
    – WS2
    Commented Dec 8, 2013 at 16:13
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    @WS2 You cannot say that long hair on men first became fashionable in the 1960s. That just isn’t true. Men with long hair has been fashionable in earlier historical periods than the 1960s, not to mention in the somewhat later glam-rock era of the 1970s, where such things were taken to an even greater extreme. Consider the Romantic poets of the 1800s, the cavaliers-vs-roundheads opposition during the English Civil War, and the popular depictions of Jesus with long hair as just a few such examples of the popularity of long hair on men, particularly on young men.
    – tchrist
    Commented Dec 8, 2013 at 16:51
  • I've read this thread a couple of times now to make sure the word androgyn has not been used. To my mind, it (and its more-famous adjectival cousin, androgynous) fit the bill here. With that off my shoulder, I did look up the word in the American OED on line, and it seems that the OED folks and I are not traveling in the same circles here in the US. They considered the word "dated" and offered up the synonym "hermaphrodite." Could I be wrong? Commented Dec 8, 2013 at 17:25
  • I'm not sure how well-known androgyne really is, compared to androgynous.
    – Ingmar
    Commented Dec 8, 2013 at 17:30
  • @tchrist It is indisputably correct that men in previous centuries had long hair. And dandyism was fashionable in the 18th. But the 1960s were the first decade of the 20th when men, in western society, wore long hair and brightly-coloured clothes. I have heard the 1960s' trend was predicted by a sociologist as early as the 1930s. He spotted a future demographic change. Numbers of young men would increase in relation to females of the same age. Males,in their teens and twenties, he predicted, would have to compete harder for mates. Hence a male fashion industry would emerge.
    – WS2
    Commented Dec 8, 2013 at 18:23

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