Adult Children Asking for Money? Use These 5 Questions

In this advice video, Evan Sanchez addresses a common dilemma faced by parents: adult children request financial help and then respond with contempt or disrespect. He illustrates the issue with a real case of a single mother who supports her daughter and son‑in‑law financially, only to be treated poorly. Sanchez explains that the underlying emotions driving the adult child’s behavior are a mix of dependence and shame, which often surface as anger toward the parent. To break this pattern, he proposes a set of five conversational questions grounded in tactical empathy. Each question is designed to label emotions, reveal impact, connect support with respect, co‑create problem‑solving solutions, and envision a healthier future relationship. He details why each question works, how it shifts the dynamic from adversarial to collaborative, and emphasizes that these tools are not a magic fix and are unsuitable for cases involving abuse, addiction, or serious mental health issues. The video concludes with a brief invitation to book a coaching call for further assistance.
Chapters
Has this ever happened to you? You're sitting there and your adult child calls you and they say, "Hey, Mom, Dad, you know what? I have this huge car expense. I can't pay it. Can you help me out?" Or maybe they're asking for a security deposit or some large amount of money. Or maybe a free place to stay. So you go ahead and you actually do it. You give them the help because of course you do. You're their parent. You love them. You want the best for them. But then a few days go by, maybe a week, and you have another conversation with them and they start treating you horribly. They start treating you with contempt and disrespect, and you're sitting there thinking, what the hell just happened? I just helped you and this is how you're treating me? This is why I'm bringing this up, because I actually get a call with this exact situation where the mom generously is letting her daughter and her boyfriend stay in her apartment in San Diego at a reduced rate. The mom is living in Florida, so she moved out of her place to have this happen. Not to mention, she paid all of her daughter's college, and she's a single mom and has zero spousal support. So an amazing act of generosity. And then she calls me and she says, "Hey, Evan, you know, when I have these conversations with my daughter, she just disrespects me. She treats me with contempt, and I don't understand what's going on." So this is why I'm making this video. I thought if there were some questions I could give to this mom that would help the conversation in a way that the mom can set a boundary, but also open up the relationship to be better and more productive? Wouldn't that be great? So here are the 5 questions that I came up with. And before I talk about them, I have to say these questions will not magically erase the disrespect. But what they will do is they will interrupt the pattern. They'll make the adult-child pause and reflect, and they will help set a tone for what is okay and what's not okay. But before we get into them, I want to explain why this dynamic is so common. The reason why this is so common is because from the young adult's perspective, the emotion underneath their behavior is usually a messy mix of dependence and shame. You see, they need your support, but they feel uncomfortable needing it, and that's where this comes from. And what happens is that inner tension that they're feeling often explodes outward as anger aimed at the person who feels the safest, and unfortunately, that's usually the parent. And it can feel personal. That makes sense. But most of the time, it is not actually about the parent at all. It's not about you. It's about what's happening inside them. Now, the Five Questions I'm going to give you are going to help break that emotional pattern and calm the situation down while also setting clear boundaries. Now, the reason why this works is because it's based on tactical empathy. What you're going to be doing in these 5 questions is you're going to be saying, "Listen, I hear how you feel." And the way that you're talking to me is not okay. Gee. So that's the strategy. Okay, let's get into it. Let's go with the first question. So the first question is what I call the labeling question. Now let's go back to our example. Okay. The daughter says she needs $1,000 for a car repair. The mom says, "No," and the daughter snaps back with stress and anger at the parent. And in most situations, the parents are going to defend themselves, or they're going to get angry too and escalate the conversation. So here's a better approach to how to handle this. When they're coming at you, you can say calmly, "It sounds like you're feeling overwhelmed and panicked right now. Is that right?" Now, here is why this works. First, what this does is the question bypasses the attack and goes straight to the emotion beneath it. When someone is emotionally flooded, the thinking part of the brain shuts down. Labeling the feeling literally forces the brain out of fight mode and into reflection. The second reason why this works is because it is really hard to keep yelling at someone who's trying to understand your emotional state. Anger does not really mix well with trying to be understood. And third, adding "Is that right?" at the end gives them a sense of control. People who lash out often feel powerless. So, by asking "Is that right?" that gives them back some agency and lowers their need to fight. So, what this question does is it really shifts you from being opponents to being on the same side. So question number 2, this is what I call the impact question. And this question is good because once the tension lowers, now you can set a gentle boundary. If the daughter says, "You never help me the way you say you will," the parent can simply respond, say, "When you said I never help you, I feel taken aback. I'm curious, how do you think that comment would land with me?" Whoa, this is a great question because the reason why this works is because you're naming the impact without accusing them. You're not saying, "You're rude. You're being a jerk right now. How dare you?" What you're saying to them is, "This is how I felt." And the beauty of that is that this keeps them from going into shame or defensiveness. And the phrase, "How do you think that would land with me?" forces reflection. Most adult children who lash out are not imagining the effect of their words. This moment brings them back to awareness. Now, if they respond with, "I don't know, I wasn't thinking," that is a real breakthrough right there. You've just taught them emotional accountability. Okay, now we're up to question 3. This is a support and respect question. Now, this one is powerful, especially around money. So, the first two questions open the door, and now the parent can say, "How am I supposed to feel good about helping you financially when I feel disrespected in our conversations?" Here's why this question works so well. What you're doing by asking this question is you're making a connection they will never make on their own. You see, they separate the support they want from the behavior they are giving. This question brings those together clearly, and it is not a threat. You're not saying, If you talk to me like this again, I will stop helping. That's not going to help. Instead, what you're saying is, help me understand how this relationship is supposed to work. It's the Jerry Maguire tactic of help me help you. And what this does is it gives them responsibility without putting them in a corner. Quick pause here. If these questions resonate with you, but you feel nervous about using them with your adult child, I would invite you to book a call with me. This is not a coaching session. It's just a time to talk through your situation together and see if coaching is a fit. No pressure at all. The link is below. All right. Let's keep going. Okay, question number 4. This is what I call the problem-solving question. So now that the emotional fire is out and the boundary is clear, now we can move into collaboration. The parent can now say this: This way of communicating is not working for either of us. What do you think is a fair and respectful way forward, and what would that look like? I love this. Here's why this works. This question is working because now you're shifting the dynamic from parent and child into two adults solving a problem together. You are acknowledging this is not working for either of us. Which puts you on the same team. And asking them what fair and respectful looks like gives them ownership. When they help create the boundaries, they are more likely to honor them. And this is where a healthy adult relationship begins. Okay, we made it. We're on the last question, Question 5. This is the vision question. So, as this conversation is winding down, the parent can now ask this question: Putting this aside for a moment, what would a great relationship look like for us a year from now? Now, this question is powerful for a lot of reasons. First of all, it's zooming out and away from the conflict. You're looking at it from a 30,000-foot view. And it also shifts the conversation to the future. It tells them, listen, I still care about you. You're my child. I love you so much. And I still see a future with you. It also taps into their deeper values. Even struggling children want connection, and this question helps them express it. And once they can describe what this future looks like, now you have a shared vision you can both move forward with. So, we made it to the end. We got through all 5 questions, and I hope these are helpful. I hope you can use them. But I want to remind you that these are tools. They're not a magic wand. They take practice, and you may have to do them more than once and at different stages. But what they are designed for is for disrespect that comes from stress, immaturity, and old family patterns. Now, to be clear, these are not for situations involving abuse, addiction, or serious mental health challenges. Those require stronger boundaries and professional help. But for a lot of you parents out there who keep on giving and get this contempt in return, these questions can change everything. They calm the attack, they create structure, and they open space for a healthier relationship. Because as a parent, you have done so much for your child, and now they're a young adult trying to figure out their way, and you still want to be there for them. You still love them and care about them deeply. And this is a way to support your child and still insist on being treated with kindness. So start with one question, and you might be surprised at what shifts. And of course, if you want help preparing for these questions, book a call with me. Link is down below. Thanks for watching, and I'll see you in the next video.
More from Evan

How To Enforce Household Rules With Your Adult Children #parenting #family #chores

Why Gen Z Isn't Broken: What Parents of Stuck Grads Are Missing (with Ryan Vet)

When Helping Your Adult Child Becomes Enabling #parenting #family #relationships

Don't fight over their gaming habits—try this instead #parentingadvice #boundaries






