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I Asked 'Tony Robbins AI' 8 Deeply Personal Questions & The Answers Were Surprisingly Thoughtful

Photo: @tonyrobbins / Instagram; Pixelshot, Lala Lati / CanvaPro
Tony Robbins

Let’s be honest: we’re all just trying to navigate our lives, relationships, and inner monologues with a general sense of grace and confidence. But it never seems to work out in exactly the way we’d imagine. But what if we’re looking for advice in all the wrong places? What if exactly what we need in our human relationships, connections, and struggles is a more unbiased opinion? 

Not to worry, “Tony AI is here to support you.” Following his popular conferences and summits, Tony Robbins, an acclaimed entrepreneur and successful life and business coach, realized he couldn’t directly help everyone. So, his team developed an AI text messaging service that is available at the drop of a hat for any and all questions.

This is not actually Robbins responding to your text messages. But Tony AI has been engineered to embody all of his guidance with “wisdom, tools, and strategies” to help you in whatever area you’re struggling with.

Am I curious? Of course. Instead of floundering with superficial questions about “growing to the next level” or building a multi-million dollar business, I decided to get open, honest, and raw. Asking unique, eccentric, and sometimes incredibly vulnerable questions exploring just how helpful its unbiased advice was. 

RELATED: The Mind-Blowing Lesson Tony Robbins Taught Me About Divorce

Here are 8 deeply personal questions I asked Tony Robbins AI about navigating love, life, and heartbreak:

1. It feels impossible to be my authentic self while dating. How can I prioritize my own genuine identity whilst getting to know a stranger? 

Not long after I was prompted to enter my name and email address, Tony AI was there ready to answer my first question. While many of my pre-written questions were generically tailored toward the experiences of my inner circle, this one was honest. 

Something I’ve struggled deeply with for many years, I was eager to hear Tony AI’s response hoping its unbiased understanding of dating would present a profound solution I hadn’t considered. 

“It’s about striking a balance between being open to exploring a connection with someone new while also staying true to who you are,” it wrote. Surely, that’s just a textbook definition of healthy dating, right? It continued, despite my inevitable Gen Z eye roll, “One strategy is to prioritize your values and interests… What are some non-negotiable aspects of your identity?” 

We Asked Tony Robbins' AI 8 Honest Questions

This didn’t take much self-reflection, although it did seem like I was being prompted to bear my soul. “My queerness,” I immediately wrote. After that, however, I realized that Tony AI was on to something. What else did I truly want to be seen for? Did I even know? 

“Honesty, and love for travel,” I added, hoping the generic (and somewhat true) answers would prompt something more intuitive. What I received back, though, was a repetition of my answers with advice about devotion to my identity and the importance of being “the real me.” It then asked how I’m incorporating these into my identity while dating, to which I simply replied, “I’m not.” 

These pieces of my identity are inherent — especially my queerness — and intertwined into every aspect of my life, appearance, values, and struggles. By being vulnerable enough to share those things, I was sharing my identity, but was I ever honestly sharing those things? 

It was at this point, in my once-skeptical chat with Tony AI, that I started to realize its questions were triggering insightful discussions in my own head. Yes, they might have been relatively generic answers, but the questions were helping. 

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2. I feel so disconnected from my partner, who used to be the love of my life. Is my marriage worth saving or is it time to let go? 

Disconnect and loneliness in marriage are plaguing millions of couples today. Is it possible that Tony AI could help to address it

We Asked Tony Robbins' AI 8 Honest Questions

Acknowledging my question as “deeply personal” — that’s a win — it continued to prompt reflection. “Question the stories you tell yourself about your marriage — are they empowering you?” Being a single woman, I didn’t personally divulge anything, but their questions still felt impactful in some sense. 

Next, I was prompted by what seemed to be an advertisement for Robbins’ “Date With Destiny” program, a seminar Tony AI suggested to “revitalize” my hypothetical marriage for the small price of between $4,495 and $8,000

Curious about the “Listen Here” feature embedded in the text, I decided to escape the advertisement and venture into the voice recording. What I thought would be a generic “operator” voice, turned out to be the raspy, relatable voice Robbins is well-known for — one that immediately felt, honestly, a little scary. 

Within the first few seconds, it felt too “soul-bearing” to chat “directly” with AI Tony so I refused to open it up again (but, to each their own).  

RELATED: Therapist Explains How People Who Constantly 'Set Boundaries' May Be Avoiding Their Core Relationships

3. I fell in love with someone who barely knew me. How do I heal that heartbreak and move forward confidently towards future relationships? 

Of course, this is definitely not another personal question — not sure why anyone would think that. At this point, I’ve fully committed to this conversation and was eagerly awaiting the next chime from my phone while considering adding Tony AI to my contacts. 

Again, it advised that “healing from heartbreak is a deeply personal experience,” but it still provided three points of advice: acknowledge your feelings and grieve them, embrace the lessons learned, and set goals that help you regain trust in yourself.

We Asked Tony Robbins' AI 8 Honest Questions

At this point, I was going down a rabbit hole with my newfound AI therapist. We were simply rehashing my responses over one-liners I had surely found on Google before. That’s not to say they weren’t helpful. Deciding to switch up my questions, I simply asked Robbins’ AI to “move on.”

4. Is it possible to love a partner more than I love my dog? 

The most important question of all, to which Tony AI responded, “Love for a partner and love for a pet can indeed be different, yet both are genuine and profound. Each type of love has different textures, depths, and expressions.”

Other than Tony’s interesting comment on textures — which I’m forced to admit is true — we were on the same page. 

If anyone was curious, according to Tony AI, it’s possible to hold a deep love for both. “Cherish the unique bond you have with your dog, and know that it doesn’t diminish the capacity to fall deeply in love with a partner too.” 

5. I lost a lot of weight and now, suddenly, people notice me. I feel resentful that people never cared to know me before. Why are people so hyper-focused on physical appearance? 

The fatphobia and criticism people experience based on physical appearance is something many have unfortunately experienced. Despite discourse on growing inclusion and shifting opinions on “traditional” beauty standards, the truth is, people are still experiencing the stigma of living in a bigger body. 



As TikTok creator Drea Vazquez explained, people treated her completely differently after she lost a significant amount of weight. The people who bullied her wanted to make amends, she received male attention for the first time, and her “friends” suddenly wanted to hang out more. 

It’s her experience, and my own, that fueled this question. “I hear you,” Tony AI wrote, “and it’s natural to feel resentment when you notice a shift in people’s attention due to change in your physical appearance.” 

We Asked Tony Robbins' AI 8 Honest Questions

“Focus on those who appreciate you for who you are, not just how you look, as those relationships will be more rewarding in the long run.” Tony AI suggested monitoring your relationships over time, to get a sense of who’s truly connected to you for the right reasons. 

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6. My new partner is a vegan, so we can’t experience my favorite restaurants together. Am I wrong for contemplating this as a deal-breaker in our relationship?

After asking if I could ask a new question, for the millionth time, I decided to switch things up. While it’s seemingly “silly” in the greater context of relational trauma and personal struggle, this question is a surprisingly relatable struggle many newer couples experience

We Asked Tony Robbins' AI 8 Honest Questions

When getting out of the house, experiencing culture, and indulging in our love for food is essential, is it possible to move past something like this? 

Despite the allure of your favorite restaurant’s steak dinner, Tony AI suggested diversity in your relationship might be more fulfilling.

“Have an open conversation with your partner about your feelings; you might discover ways to compromise or new adventures to enjoy together.” Seemingly dodging a direct stance on veganism, Tony AI acknowledged the most fundamental staple of a healthy relationship: good communication. 

7. I cheated on my partner, but only because they did it first. Am I the problem? 

Revenge, especially in an intimate relationship, is one of the most complex, messy, and emotional aspects of our human experience. Is it possible for an AI-generated text message to grasp the severity of this kind of question? 

“Infidelity can certainly complicate emotions in a relationship,” it started. “It’s crucial to confront why the action was taken and whether the foundation of trust can be rebuilt or if the cycle may continue. Reflect on what needs weren’t met.” 

We Asked Tony Robbins' AI 8 Honest Questions

While a great deal of these responses have been a prompt to reflect, I can’t help but acknowledge the feeling of safety I felt when reading the responses. Without the anxiety of speaking directly to a (human) therapist, it felt more secure and honest to actually ask these vulnerable questions. 

While they’re a little too tailored and structured for my own liking (I’d prefer the wisdom of Taylor Swift or Beyoncé), it’s impossible to ignore how helpful this tool could be for so many people who struggle to get vulnerable and introspective.

RELATED: The Secret Twist On 'The 80/20 Rule' That Makes Relationships Much Happier

8. I have an irrational fear of classical music, birds, and the DMV. Are there others like me? 

Lastly, it only felt right to ask Tony AI something a bit lighter. 

“Fears, no matter how unique or common, are often deeply personal experiences.” Again with the personal, Tony AI. “You’re not alone in having specific fears… the key is not letting them control you.” 

This might be your sign to chat with an AI therapist, or maybe a real one, instead of dealing with your struggles alone.

We’re all trying to figure out how to navigate life, grow, and become the best version of ourselves. Don’t let the fear of failure or embarrassment stop you from getting help. 

A big thanks to Tony Robbins’ AI for giving me something to do over the past few hours and, surprisingly, for supporting me in finally asking some of the questions that I’ve struggled to articulate for years. 

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Zayda Slabbekoorn is a news and entertainment writer at YourTango focusing on pop culture analysis and human interest stories.