
I don't really really get into games with that kind of relationship/dating mechanic. I'm horrible enough at that as it is in real life But your story reminds me of some of the things I experienced in the Harvest Moon/Story of Seasons/Rune Factory games.
In one of the Rune Factory games, Farmer Man Cary tried to woo a female knight because she was strong and tough and we could fight monsters together.
In one of the DS/3DS (can't remember) Harvest Moon/Story of Seasons games, Farmer Man Cay took a liking to the female blacksmith. She was a little asian lady though and didn't seem to fill the blacksmith type, but Farmer Man Cary didn't care. I THINK her name was Iroha in the game.
My favorite was from another Harvest Moon/Story of Seasons game on the DS/3DS. She was a pretty and flirty writer named Iris, and Farmer Man Cary was smitten!
And those are all the ones I remember.