A short background of my friend. He isn’t a quiet or shy guy per-say. For example, he was the president of his college Fraternity. However, he tends to avoid awkward situations at all costs. He’s the type of guy to pretend like he doesn’t see the person he talked to in high school standing right in front of him. He would rather pretend like they don’t exist than make pleasantries. If other person approaches him though he won’t be weird about it.
Ok, so on to the problem at work he’s having. He recently began working at a real estate firm. There is this sort of secretary/assistant/clerk that’s been there for years. My bad I don’t know her exact title, but we’ll just call her Amy. Amy is a nice gal and has been helping my friend out with setting up meetings for house showings etc. My friend being the nice guy that he is wanted to give a show of appreciation for the work she’s done for him the first month. So, he offers to buy her lunch one day. She took up the offer and all was well. She was satisfied with her sub, and he felt good for doing a nice thing.
However, little did my friend know he just opened up pandoras box. Since that day she has been asking my friend for lunch every other day. This has been going on for a month now. Some days my friend wouldn’t even be eating out, but he would be going to a house showing, and she would ask him to pick up food for her on the way back. For the record, she never offers payment for the food.
We’ll call my friend Mike. Every time she wants to request food from him she says, “Hey Mike wanna do Amy a favor?” For example, Today, he was going to pick up some paper work downtown. Turns out Amy managed to get that paperwork delivered to the office, saving him a trip. So, what does she do? “Hey Mike since I saved you a trip, do you want to do Amy a favor?” And he actually went and got her lunch. It’s absurd.
He doesn’t know what to do in this situation. I told him to just tell her you cannot afford it, but he cannot bare being put in an awkward situation. Confronting her straight up about it seems out of the question for him. What do you guys think he can do?
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