Most people struggle with speaking up or even saying “no.” You've never had that problem. You've always been confident and assertive, but the same can't be said for a loved one. This is something that will become abundantly clear on June 3rd when Mercury squares Neptune. The problem isn't hurt feelings; it's that you're not understanding how this person wants to do right by you but also feels like you're being too demanding. Your response may be for them to say so, but not everyone can. This is complicated territory so you'll need to slow down and be more sensitive as you negotiate it.