I think Bilbo's bachelerhood could use a bit more analysis. He was a initially a Hobbit of the genteel end of society. By having his adventure, he tarnished his good reputation. Furthermore, after his adventure JRRT tells us in FOTR that he often had queer visitors in the form of passing by Elves and Dwarves. Thus, despite his unquestionable wealth his reputation remained tarnished due to his guest's as much as his adventuring. I don't imagine this behavior is anything a self respecting female Hobbit would have put up with.
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