Talk to farmer Giles at his now flourishing farm in Brightwood (it’s come a long way in a few years!). He will tell you that he wants to retire and give it all to his son. He will give you a photograph, after you have it, head into the south field to talk with his son. After a brief conversation, it’s time to set off to Bowerstone to find a worthy marriage candidate.
Walk around town and show the photograph to any villager you wish to go on a date with him. A villager will not go out with him until they trust you, so once you have picked a suitable target, do a bit of dancing and throw out some other expressions until they like you.
Once they trust you, give them Rupert’s photo. They will say agree and give you their details, take the details back to Farmer Giles and Rupert who have now moved from the field into the main farmhouse to complete the quest.