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AI Gift Shopping: Helpful Tools or Overhyped Hassles? Why Generative AI Still Can’t Handle the Personal Touch 

 December 27, 2024

By  Joe Habscheid

Summary: The rise of generative AI has raised expectations about its ability to handle tasks autonomously, but how well does it actually perform when given real-world responsibilities? Lauren Goode’s experiment—using various AI assistants for her holiday gift shopping—highlights both the strengths and limitations of these tools. While AI can assist with recommendations and information gathering, the nuances of human preferences and the emotional weight of gift-giving remain outside its grasp. Her experience underscores that AI may be helpful but not independent as a solution for such personal tasks.


The Appeal of Delegating Shopping to AI

Shopping, especially during the holidays, often becomes a source of stress for many. The sheer effort of finding thoughtful, unique gifts for everyone on the list can be overwhelming. This is precisely why Lauren Goode decided to explore whether AI chatbots and assistants could take the workload off her shoulders. By using platforms like Perplexity AI, ChatGPT, Google's Gemini, Anthropic's Claude, and Amazon's Rufus, she aimed to streamline her gift-giving process.

What she found was a mix of promise and pitfalls. While these platforms demonstrated notable progress in parsing product descriptions and generating suggestions, they fell short of being truly autonomous shoppers. Goode's adventure reveals valuable insights into the current state of AI technology when applied to something as complex and nuanced as holiday shopping.

AI Recommendations: Impressive but Imperfect

Gift-giving is, at its core, a deeply personal experience that requires understanding the recipient’s personality and preferences. This is where the limitations of AI become most evident. Goode tested how well these systems performed by shopping for five individuals, including someone with a passion for baking. While ChatGPT impressed her with thoughtful and inventive ideas, others, such as Perplexity’s “Buy with Pro” feature, came across as little more than glorified search engines, offering utilitarian results rather than meaningful suggestions.

The issue wasn’t just the quality of recommendations but also the effort required to get there. Lauren had to write and rewrite her prompts, often guiding the AI with extensive instructions and clarifications. Even with its vast pool of data, AI struggled to account for the emotional weight and subtlety involved in choosing a truly meaningful gift.

Where AI Falls Short: Nuance and Execution

Despite its capabilities, AI failed to bridge the emotional gap. Selecting gifts goes beyond finding “something nice.” It involves connecting on a personal level, making choices that resonate with shared memories, values, or interests. This is not only something AI platforms can’t yet do; it’s something they may never fully replicate.

Another challenge Lauren encountered was the actual purchasing process. None of these tools could fully automate the buying step. She had to leave the AI’s interface, manually navigate retailer websites, and ensure the orders were completed. This added layer of effort underscored the fact that these systems are assistants, not agents capable of taking complete control of the process.

Even worse, some of the gifts arrived late, and certain suggestions missed the mark entirely. For instance, she ended up giving cash to her niece after failing to find a suitable present with AI assistance, showing how technology often falls back on default or uninspired solutions when it struggles.

The Role of AI in Gift-Giving: A Work in Progress

Lauren’s experiment serves as a reminder of the potential and the limitations of generative AI. For businesses, it opens a conversation about where automation can be useful and where human understanding remains irreplaceable. AI excels at tasks requiring data analysis, quick comparisons, or broad-strokes recommendations. But it stumbles when it hits the intangible aspects of decision-making—like gauging the emotional significance of a gift or tailoring a product to an individual’s unspoken preferences.

The experience also highlights the gaps in execution. For true autonomy, AI tools need to handle the entire workflow, from selection to purchase to delivery. Until then, they remain partial solutions requiring substantial human input to produce worthwhile results.

Takeaways for AI Development and Users

The key takeaway is balance. Users shouldn’t view AI as a one-size-fits-all solution. Instead, it’s a collaborative tool that can enhance efficiency while still relying heavily on human guidance. Developers, in turn, need to focus on creating systems that better understand context and emotional nuance and integrate seamless execution capabilities.

The future looks promising. As these systems evolve, they may eventually be able to process deeper levels of user data to refine their recommendations and even automate more logistical aspects of shopping. Until then, however, they serve best as supplementary tools—not substitutes for personal touch and effort.


Lauren Goode’s experiment is revealing, not because it proves AI’s infallibility, but because it reminds us of its limitations. Generative AI holds enormous potential, but it can’t yet completely take over tasks involving human relationships. And perhaps, for something as meaningful as holiday gift-giving, that’s a good thing.

#AIShopping #GiftGiving #GenerativeAI #HolidayShopping #TechWithLimits

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Featured Image courtesy of Unsplash and Jess Bailey (f94JPVrDbnY)

Joe Habscheid


Joe Habscheid is the founder of midmichiganai.com. A trilingual speaker fluent in Luxemburgese, German, and English, he grew up in Germany near Luxembourg. After obtaining a Master's in Physics in Germany, he moved to the U.S. and built a successful electronics manufacturing office. With an MBA and over 20 years of expertise transforming several small businesses into multi-seven-figure successes, Joe believes in using time wisely. His approach to consulting helps clients increase revenue and execute growth strategies. Joe's writings offer valuable insights into AI, marketing, politics, and general interests.

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