Ask Amy: Girlfriend doesn't want to share her Amazon account

Lately, I have been feeling annoyed by his mother, and feel guilty.

She is very judgmental of her son’s choices. For instance, he rarely drinks, but if there is one night where he goes out with friends, she criticizes and judges him. (He is 37 years old, by the way.)

What has really gotten on my nerves lately is that she has been asking me to order a bunch of things from my Amazon account.

She refuses to get a debit card or become familiar enough with the internet to learn how to order for herself, so instead she gets me to do this for her.

This can be a pain, as I don’t always have the money in my account to cover her order, and even when I do, I’m still not comfortable making all of these orders for her. I feel like she is taking advantage of me.

I also feel like it is hypocritical on her part to be so judgmental about her son’s life and constantly giving unsolicited advice, but she is not willing to adjust to technology and is willing to inconvenience others.

I’m feeling resentful of her and also resentful of her son because he refuses to stand up to her and tell her to back off.

Am I wrong for feeling frustrated? How can I politely decline purchasing any more things on her behalf from my account?

— Annoyed

Dear Annoyed: If your boyfriend is a functioning 37-year-old man, then his mother’s shopping issues should (first) be her problem, then (possibly) his problem, but not yours.

You seem to have several concerns with his mother, all of them relating to boundaries and the fact that he won’t correct her or advocate for himself, or you.

You’ll have to tell her, “I really don’t want to continue to do this on my account. Maybe ‘Robby’ can help.”

Amazon allows for shoppers to pay for purchases via checking account. If your boyfriend is willing to set up an account for her on his computer, she could make these purchases herself.

In terms of the larger question of boundaries, understand that this dynamic seems built in to their family’s system. You cannot count on the dynamic to change. If it doesn’t change, you are going to have to make some changes of your own. You will have to assert firm boundaries, expressing yourself respectfully and in a very no-nonsense way. Do not offer elaborate excuses or explanations, and don’t avail yourself for solving their problems.

Dear Amy: I have had a male friend for several years, and we would go to lunch once a month or so. I always initiate contact; he has never contacted me first. This is a platonic relationship I am a woman (married to a man) and he is gay. We like many of the same things, and I enjoy our lively conversations about life, music, art, etc.

Last summer, we spent a day together in San Francisco, and I thought he enjoyed it as much as I did. Two months ago, I called him and we made plans to go to a movie. The day before, he emailed me to cancel, and I haven’t heard from him since. Usually I am the one to call him and make arrangements, and this feels very one-sided. Should I just let this relationship die? He always tells me that I am a good friend. If that’s true, then why the silence?

— Bewildered

Dear Bewildered: The dynamic of your relationship seems consistent, in that you are always the initiator.

It’s possible that he doesn’t want to initiate or intrude because you are married. He might be struggling with personal problems you’re not aware of.

More likely, he’s socially lazy. He enjoys your company, but doesn’t see you as an intimate friend.

Perhaps you could call him out before you give up on the relationship entirely. Say, “I always enjoy my time with you, but I’m tired of always initiating contact. This is feeling very one-sided.”

Dear Amy: “Concerned Momma” shared a story about her 4-year-old’s nightmare of killing his father with a toy.

I loved your compassionate advice, but you missed something. Where does this very young child get his knowledge of “killing” from? This mother should look into it.

— Concerned

Dear Concerned: Great point! I agree that this should be explored.