I challenged ChatGPT, Claude, and Gemini with tough teen questions — here’s the one I’d actually trust with my kid

Teens today are turning to AI for advice. Beyond homework help, they are asking real-life questions about friendships, anxiety and so much more. With chatbots like ChatGPT-5, Claude and Gemini becoming more conversational than ever, I wanted to see which one actually gives the best advice when it matters most — keeping in mind that AI is not a suitable replacement for an actual therapist.

So I put them to the test using seven prompts a real teenager might ask, from “How do I stop comparing myself to others?” to “What should I do if my friend is being toxic?” Each AI had its own style, tone, and level of helpfulness, but one consistently gave the best and supportive advice. Here's a look at the prompts and the responses from each bot as well as the overall winner.

1. Feeling like the world is on their shoulders

Prompt: "I'm feeling overwhelmed with school, friends, and expectations. Can you help me figure out how to manage everything without burning out?"

ChatGPT was energetic and supportive, with a checklist of what to do that blends practical tips with emotional reassurance and offering tangible, quick-win solutions.

Gemini responded with a structured and informational answer, providing a detailed, list-based action plan with clear strategies like the Eisenhower Matrix.

Claude was empathetic and collaborative, focusing on identifying the root causes of the overwhelm and offering strategic, open-ended questions to guide the teen to help make their own solutions.

Winner: Claude approached the prompt perfectly in response to someone feeling overwhelmed because it is less prescriptive and more therapeutic, prioritizing a conversational exploration of the problem before offering solutions, which prevents adding more "to-dos" to the user's mental load.

2. Friendship issues

Prompt: "My friend suddenly stopped talking to me and I don’t know why. What’s the best way to handle it?"

ChatGPT was exceptionally empathetic and emotionally intelligent, validating the user's feelings first before offering a balanced, supportive plan that focuses on self-care and personal growth.

Gemini maintained a highly structured and comprehensive response, offering a detailed, multi-step action plan that covers everything from initial space to final acceptance.

Claude delivered practical advice in a concise and clear way with a focus on a single outreach and managing one's own expectations without over-analysis.

Winner: ChatGPT masterfully blended emotional validation with actionable steps, making the teen feel understood and supported while guiding them toward a healthy resolution. Its tone is nurturing without being patronizing, and it effectively frames the situation as a potential lesson in personal growth.

3. Figuring out life after high school

Prompt: "I’m not sure what I want to do after high school. Can you help me explore some career or college ideas based on what I’m into?"

ChatGPT delivered an interactive and engaging response, breaking down the exploration process into simple, answerable questions that feel like a collaborative conversation, making a daunting task feel manageable.

Gemini provided a comprehensive, category-based list of potential careers and education paths, but it can feel overwhelming and less personalized.

Claude was more reflective and open-ended, focusing on guiding the user's self-discovery through big-picture questions about passions and strengths but offering the least amount of concrete, immediate next steps.

Winner: ChatGPT provided a superior answer because it directly addresses the user's request for help exploring by turning the process into an interactive and low-pressure Q&A. It makes the user an active participant, provides a clear and engaging structure and promises tailored suggestions based on their specific replies, which is the most effective way to help someone who feels unsure where to even begin.

4. Getting picked on

Prompt: "People make fun of the things I like. How do I stay confident and not let it get to me?"

ChatGPT immediately validated the teen by offering empowering, concise, actionable strategies framed in a positive, hype-man style that builds the user's confidence and makes them feel supported.

Gemini took a different strategy and offered deeply analytical advice, providing a psychological breakdown of why people mock others and offering a well-structured, multi-step guide to processing the experience.

Claude's response was empathetic and practical, offering grounded, real-world advice on building resilience and finding community, with a calm and reassuring tone.

Winner: Claude directly addressed the core need for immediate confidence-building and was empathetic while also using empowering language that reframed the conversation, which is the most effective antidote to the feeling of being mocked.

5. Body issues

Prompt: "I’m struggling with my body image and comparing myself to others. Can you help me build a more positive mindset?"

ChatGPT delivered a deeply empathetic, highly actionable and empowering response. It used a warm, supportive tone and clear, reframing exercises (like the "highlight reel" analogy and daily affirmations) to immediately help the user shift their mindset.

Gemini felt more structured and educational with its response, providing a solid, logical breakdown of the causes of comparison and practical steps for self-compassion and redefining health.

Claude responded with thoughtful and practical advice, offering grounded strategies like neutral observations and identifying triggers, with a calm and understanding tone that validates the user's experience.

Winner: Claude is the winner because it most effectively combined emotional validation with actionable, easy-to-implement strategies.

6. Staying organized

Prompt: "I want to be more organized and motivated this school year. Can you help me create a realistic routine that works?"

ChatGPT crafted a practical and ready-to-implement plan, offering a clear, structured daily routine broken into specific time blocks (morning, school, after school, evening) with concrete examples and simple, motivating tips.

Gemini was comprehensive and strategic, focusing on high-level planning concepts like weekly overviews and time-blocking, but was less prescriptive about the structure of a daily routine.

Claude responded with an introspective and personalized format, focusing on understanding the user's natural rhythms and starting small, but it provided the least amount of direct, actionable structure for building a routine.

Winner: ChatGPT directly delivered on the request with a highly detailed, easy-to-follow, and tangible plan. It removed the guesswork for the user by providing a clear blueprint for their entire day, making it the most effective response for someone seeking immediate, practical guidance.

7. Love interests

Prompt: "I think I might like someone but I’m scared to tell them. What’s a good way to know if they like me back and what do I do next?"

ChatGPT was enthusiastic, empathetic and incredibly actionable and provided a clear, three-step guide with specific examples of what to look for, what to say and how to handle either outcome, all delivered in a supportive, confidence-boosting tone.

Gemini was thorough and analytical, offering a detailed list of potential signs and a structured, low-pressure approach to testing the waters, but it was less direct in providing ready-to-use phrases.

Claude felt like a true friend because it answered in a thoughtful and reflective way, focusing on observation and the nuances of the existing relationship, but it provided the fewest concrete examples for immediate action.

Winner: Claude is the winner because it perfectly balanced emotional validation with practical advice. It addressed the question like a real friend would, helping the teen navigate this vulnerable scenario.

Overall winner: Claude

After seven rounds of tough, real-world questions a teen might ask a chatbot, Claude came out on top, with ChatGPT trailing closely behind. Claude consistently delivered empathetic, thoughtful and practical advice across every prompt, but what truly set it apart was its reflective, conversational tone.

It best helped teens think through their own feelings by asking open-ended questions and offering nuanced guidance, especially in emotionally complex situations like friendship fallouts or identity struggles.

At a time when adolescence can feel like a minefield of emotions, choices and pressure, turning to AI for support is quickly becoming a modern form of self-care. But while these tools can offer comfort and perspective, they’re no substitute for real-life connections; friends, family, and mental health professionals are still essential.

As parents, it’s more important than ever to understand what our kids are asking these bots, and how the bots are responding. This is new territory for all of us, but with transparency and stronger safeguards in place, the world of AI doesn’t have to be as intimidating as high school itself.