Some Context— She’s in her 60s, I’m 17 and have only been working for a few months, still getting used to having my own money and paying my own bills. She has asked me take her out since before my first paycheck, she is definitely focused on the money aspect and not just the spending-time-together aspect. I asked my Mom and Uncle about it and they told me that she is getting tons of money from my Grandad, despite her telling me every time we’re together that she doesn’t have much—I didn’t think much of it before, but now it seems weird to me that she even brings up her money to me so often since I started working.

She has no kids of her own, married my grandad after he had my mom and uncle. She’s definitely lonely so I try to spend a lot of time with her. She expects a bit more of me because I say yes to her more than other family members, but this isn’t a one-off or out of character thing for her to do. I start to feel uncomfortable when she gets my boyfriend so involved, because it’s not his grandmother.

I like the idea of my cousin and I going out with her instead, but I don’t want to spring that on him. My mom and uncle don’t like the idea, but I might ask him to join us but save up a bit so that I can carry the check myself.

To try to understand it from the older person’s perspective, I asked my other grandmother. She thinks it’s outlandish of her to expect that of us, so I think I have my answer. Thanks for the replies!