Anah is called "daughter of Zibeon" at Genesis 36:2 and 14, but multiple masculine forms are used to describe this person in 36:24; and in the next verse, Aholibamah is listed among "the children of Anah." Was this a man or woman? To make matters worse, both Zibeon and an Anah are listed among "sons of Seir" (36:20), while an Anah is said to be a child of Zibeon at 36:24. What are we to make of this?
Was Anah—the parent of Aholibamah, wife of Esau—a man or woman (Gen 36:20)? And, if a man, was he Seir’s son or grandson?
Let us take up the last question first. There is an Anah is among “the sons of Seir” at Gen 36:20, yet Zibeon is in that same list of sons, and Zibeon is said to be the father of an Anah, though perhaps a different one.
Indeed, I believe that there were two Anahs, one being Seir’s son, and the other being that Anah’s nephew (and Seir’s grandson). This is not necessarily the case, because there is no special word for “grandson” in Hebrew, and it is possible that Anah the grandson of Seir was included among his sons because of his importance as father of Aholibamah. But I am inclined to believe there were two Anahs, because at 36:24 the son of Zibeon is described in a way that suggests there was another: “this was that Anah that found the mules [probably should be "hot springs" or "giants"] in the wilderness”, i.e., this wording seems to suggest that it was not his uncle Anah.
Now, as to whether this was a man or woman, Anah is called “daughter of Zibeon” not just at 36:2 but also at 36:14. The trouble here is that Anah the child of Zibeon is certainly identified as male at 36:24, which uses masculine pronouns/endings. Notice also that in the next verse, “Aholibamah the daughter of Anah” is put among “the children of Anah” (36:24). Thus, according to 36:20-25, Seir fathered Zibeon, who fathered Anah, who fathered Aholibamah. And thus the Anah mentioned at 36:24, described with “he” and “his,” is definitely the same Anah that is mentioned in 36:2 and 36:14 as “daughter of Zibeon.”
I am inclined to conclude that “daughter” (בַּת or bat) in the latter is a scribal error, which is quite possible, especially since its orthography could be confused with that of the word for "son" (בֵּן or ben), in rapid copying of a relatively "boring" passage of scripture.