Yes, the "details" of such situations are difficult, if not impossible to know.
As I'm thinking about it, I can recall at least two such situations that I was aware of in the vicinity of my NYC congregation.
The first was the daughter of a new elder. This was during the post-1968 years. I knew the girl and her family. It seemed out of nowhere that she and a *much* older brother were "keeping company." Probably her father felt that it was silly for her to get involved with a guy near her age when this old guy could offer her security. She developed cancer and died tragically young. Too bad there'll be no resurrection for her.
The second was an odd situation. A guy who went to Bethel for a couple of years to avoid the US military draft started making the circuit of NYC congregations, obviously looking for a connection. This guy was at least a little bit of a narcissist, he didn't meet his "goals" in hours, etc, and seemed to have no interest in "reaching out" or building a career. He found a girl who was a few notches over what he was worth, but she was in a vulnerable situation. She went our with him because he was different from the other Bethelite Wolf-Men and he was interesting in some ways. Then her elders started talking some sense to her about why was she with this loser? She started having doubts and tried to end their engagement, and Brother "I'm a Bethelite!" BLACKMAILED her into going through with it, saying he would drag her to a judicial committee and get her disfellowshipped for "leading him on" and "toying with his affections!" So the got married. Brother Loser was unable to support his family and his wife in desperation to get out of the abusive marriage, had an affair.
She got disfellowshipped but ended up happy and he lives in a van down by the river, spiritually speaking.
There was another "elder's daughter" story similar to the first, but without the tragic ending. Young, attractive daughter, horny older "theocratic man," Dad shakes his hand and says "take her."
Daughters are the property of their fathers under Mosaic Law, right? ...and JWs are still under the Law, even though they might claim otherwise.