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In the books, Treebeard laments about the loss of Entwives (female ents), hence why there will be no Entlings (ent children). This made me wonder actually how ents breed?

Ents are a mix of trees and humanoids. They have humanoid characteristics like four limbs and tree-ish characteristics such as a bark-like skin.

Trees and humanoids reproduce in entirely different ways. Since Ents are a mix of trees and humanoids - how do they actually reproduce?

Do they reproduce like trees, humanoids, a mixture, something else?

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    When a daddy ent and a mummy entwife love each other very much... – Doctor Two Sep 4 at 16:49
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This is, rather obviously, never clarified by Tolkien. Primarily because there was no need to, in the same way it isn't clarified for Dwarves (recall Tolkien's "joke" in Appendix A: "This has given rise to the foolish opinion among Men that there are no dwarf-women, and that the Dwarves ‘grow out of stone’") or Elves, only presumed.

Instead I will paint a picture of what the Ents were like and allow you to come to your own conclusion. Firstly, Ents were far more "humanoid" than is commonly thought. Treebeard likened the similarity between Ents and their trees to shepherds and their sheep:

Sheep get like shepherd, and shepherds like sheep, it is said; but slowly, and neither have long in the world. It is quicker and closer with trees and Ents, and they walk down the ages together...
The Two Towers, Book III, Chapter 4: “Treebeard”

Treebeard clarifies that these similarities might've grown more pronounced for the Ents and their trees as they have walked "ages together" unlike the shepherds of Men who lived no longer than a century. This would suggest that they were mostly humanoid although resembled trees. A bit like a dog owner and their dog.

Secondly, while Treebeard's skin is described as bark-like, it is explicitly described as being smooth, like human skin:

Whether it was clad in stuff like green and grey bark, or whether that was its hide, was difficult to say. At any rate the arms, at a short distance from the trunk, were not wrinkled, but covered with a brown smooth skin.
ibid.

Thirdly, Ents are described (repeatedly) to be rather troll-like, one example from earlier in the above quote:

They found they were looking at a most extraordinary face. It belonged to a large Man-like, almost Troll-like, figure, at least fourteen foot high, very sturdy, with a tall head, and hardly any neck.
ibid.

Finally, how Ents came to be, what they 'are', I have emphasised the parts that really need to be read, the rest is contextual:

All have their worth,' said Yavanna, '... But the kelvar can flee or defend themselves, whereas the olvar that grow cannot. And among these I hold trees dear. Long in the growing, swift shall they be in the felling, and unless they pay toll with fruit upon bough little mourned in their passing. ... Would that the trees might speak on behalf of all things that have roots, and punish those that wrong them!'

'This is a strange thought,' said Manwë.

[...]

And Manwë said: 'O Kementári, Eru hath spoken, saying: "... Behold! When the Children awake, then the thought of Yavanna will awake also, and it will summon spirits from afar, and they will go among the kelvar and the olvar, and some will dwell therein, and be held in reverence, and their just anger shall be feared. ..."
The Silmarillion, Chapter 2: “Of Aulë and Yavanna”

Ents therefore have fëar and as such are sentient beings. Whether this affects their reproduction is anyone's guess. But it is clear they have free will and as such most likely wouldn't reproduce through the rather passive means that are usually expected of a tree.

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    Wasn't there another reference that said Trolls were originally made in an attempt to create an "evil" (or controllable) race of Ents? – T.E.D. Aug 3 at 3:22
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    @T.E.D. See my other answer here – Edlothiad Aug 3 at 8:01
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    This is where the films' depiction of Ents, whilst great visually, create a misunderstanding of the books' version of Ents. As you say, in the books they're clearly humanoid and not the "tree-men" that Peter Jackson created. – Graham Aug 3 at 12:51
  • You say us to arrive on our own conclusions - now what's your conclusion eh ? – TheMadHatter Aug 3 at 16:09
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    @TheMadHatter I have outlined my opinions in the answer. My conclusion is that it doesn't matter. It has no bearing on the story, they universe, how it's presented or it's goals. – Edlothiad Aug 3 at 16:50
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Tolkien didn't say, but let's pursue this line of thought to see where it leads biologically.

Reproduction in an animal-like manner

At one time, male Ents had Entwives. One might presume that they reproduced in a similar manner to humans, with a lasting pair bond and small numbers of children (Entlings) receiving individual care. Nothing that Tolkien said about Ents would contradict this manner of reproduction. Also, Trolls are supposed to be imitations of Ents, and they are decidedly animals, not plants.

Reproduction in a plantlike manner

If Ents reproduced like trees by releasing and accepting pollen, blooming with many flowers, reproduction would be a group affair unless a couple was very careful to isolate themselves from others, and that isn't very plantlike. Considering that Treebeard treated the Hobbits as individuals rather than mere members of a horde, the young Entlings would be few, like coconuts, rather than many, like acorns, regardless of the number of flowers. Although one might suppose that husband-wife pairing might demand reproductive pairing as well, this doesn't necessarily follow: Coupling might be decoupled from reproduction. Stranger things happen in Tolkien's legendarium, but this is not the simplest explanation.

Occam's Razor suggests that Ents reproduced in an animal-like manner. But I can't forget the image of flowering Ents; it's too beautiful a concept to reject out of hand.

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