In Tolkien's Middle-earth, Men and Hobbits lived together amicably at Bree, but I recollect no suggestion in The Lord of the Rings that the Big and Little People ever intermarried despite sharing a common culture. Elves and Men, who Tolkien considered to be more different from each other than Hobbits and Men, did intermarry on very rare occasions, and could have children. Presumably a Man and Hobbit could have children together. In any of his extensive writings, did Tolkien ever mention a marriage between a Man (male or female) and a Hobbit?
No, but Tolkien has discussed Hobbits intermarrying with other races
Dating back to one of the original surviving drafts of the opening to The Hobbit, we have a concept that there was at least one Took-Hobbit who married an elf.
It had always been said that long ago some or other of the Tooks had married into a fairy family (goblin family said severer critics); certainly there was something not entirely hobbitlike about them, and once in a while members of the Took hobbits would go and have adventures.
This passage was retained with some minor changes into the original published book:
It had always been said that long ago one or other of the Tooks had married into a fairy family (the less friendly said a goblin family); certainly there was still something not entirely hobbitlike about them, and once in a while members of the Took-clan would go and have adventures.
Though after some later revisions, the current third edition text now plays this down a bit specifying that is "absurd".
It was often said (in other families) that long ago one of the Took ancestors must have taken a fairy wife. That was, of course, absurd, but certainly there was still something not entirely hobbitlike about them, and once in a while members of the Took-clan would go and have adventures.
The abandoned "1960 Hobbit", would have also kept it, just with the language changed to be a bit more in the line with The Lord of the Rings.
It was often said (in other families) that the Tooks must have some elvish blood in them: which was of course absurd, but there was undoubtedly some thing queer about them, something not quite hobbitlike, according to the manners of the Shire: an outlandish strain maybe from long ago.