Giles' Request
To start "The Blind Date," open the in-game map. Select Brightwood to go there instantly. If you want to walk to Brightwood, set "The Blind Date" as your active quest. A golden trail on the ground leads you to Brightwood. When you arrive, go to the west side of the village. You reach a farm. Enter the farmhouse and talk to the old man, Giles. He worries that his son, Rupert, is not yet married. He begs you to find a mate for Rupert.
Rupert's True Feelings
After you receive Giles' request, head to the field outside the farmhouse. Talk to Rupert, and he reveals the reason why he has not yet married. Rupert is not interested in women, but he is afraid to tell his father this. Rupert thinks that you can help him find a man to date. When you do, he promises to reveal his true feelings to his father. Rupert gives you a picture and asks you to show it to any potential suitors.
Finding Love for Rupert
Head to the Bowerstone Market to search for a mate for Rupert. You can fulfill Rupert's request and search for a man, or look for a woman to fulfill his father's request. If you do as his father, Giles, asks, you earn evil karma points. You get good karma points if you find a man for Rupert. If you want to find a woman, any single woman will do. If you prefer to find a man, look at the man's status to see his sexual orientation. Only gay men show interest in Rupert. When you find an ideal partner, select Rupert's picture in your inventory to show it to the person. The person tells you that they want to meet Rupert.
Ending the Quest
Go back to Brightwood and talk to Rupert to tell him about the mate you chose for him. If you found a woman for Rupert, he expresses disappointment, and his father tells you how happy he is. If you found a man, Rupert says he can't wait to meet him. He tells his father how he really feels, and his father accepts his choice. Regardless of the choice you made, Rupert and his father decide to sell the farm. Buy the farm, if desired, for about 75,000 gold coins.