Yes, Your Grace

Stefan should up for me for the first time Week 7. He asks for 1G for boots. You don't have to give him gold here to earn the achievement. He then comes back later during Week 15 for me. This time he has some drunken dialogue and I believe he asks you for a fishing rod. You will be given three options:

Give 1G
Give 7G for food and new clothes
Get Lost

Choose Give 7G and the achievement is yours. If you don't feel comfortable giving that kind of resource, just reload after the achievement pops. Additionally he will come back again with a new look and new perspective on life and give you back 4Gs. Also, if you help him you can call on him for 6 armies later in the game.

In week 7 a drunken guy will ask for your help. Give him one gold. He will return in week 15. This time give him gold again . He will return for the 3rd time this time he is sober and he will thank you and the achievement will pop

A visual representation with commentary of the achievement in the video.