Jennings sits next to 3 phonetic neighbors — Jenkins, Bennett, and Hennings are the closest matches by sound. Most share Jennings's English-origin cluster, so the rhythm and vowel shape carry across the list.
You searched for names like
"son of Jen (John)"
"watchful"
"dark as a raven"
"flower (disputed folk etymology)"
"member of the Kru seafaring people (West Africa)"
"little hawk"
"counselor, advisor"
"rowan tree"
"lion strength"
"spear servant"
"uncertain, possibly warrior spirit"
"at another time"
"son of Bray (from Celtic bray: brave)"
"from Airelle (Norman village)"
"honor-friend"
"good race, fine stock"
"peace, gentle"
"castle, new home"
"a natural watercourse"
"companion, friend"
"son of Ellis"
Similar sound: These names share phonetic patterns with Jennings — similar vowel sounds, consonant clusters, or rhythm.
Shared roots: Several names on this list have English origins, giving them the same cultural heritage as Jennings.
Rhythm: Jennings is a 2-syllable name. Names with the same syllable count tend to feel interchangeable when you're narrowing your list.