Another Crazy Day in AI: A New Way to Plan Your Next Getaway
- Wowza Team
- Mar 21
- 4 min read

Hello, AI Enthusiasts.
AI doesn’t do Friday nights, but we do. Before you unplug—
Booking.com is reinventing trip planning. Partnering with OpenAI, it’s making travel discovery seamless—helping you find the perfect getaway without the usual search fatigue.
Yahoo is making an AI-powered comeback, but can it reclaim relevance, or is it just another relic trying to reboot?
MIT and OpenAI researchers are looking into AI friendships. Some users treat chatbots like search engines, others like therapists. (Spoiler: some are surprisingly personal).
That’s a wrap for the week! Rest up—AI will still be making moves while we recharge.
Here's another crazy day in AI:
How Booking.com is reinventing trip planning
Yahoo’s AI bet—can it reclaim internet relevance?
MIT and OpenAI examine ChatGPT’s role in emotional well being
Some AI tools to try out
TODAY'S FEATURED ITEM: A Smarter Way to Book Travel

Image Credit: Wowza (created with Ideogram)
Ever wanted a travel buddy that gets your vibe—like a “cheesy romantic getaway” or hidden gems beyond the usual tourist spots?
Booking.com is transforming the way travelers explore destinations and book accommodations by integrating OpenAI’s language models into its platform. In an article, OpenAI details how Booking.com is enhancing travel discovery, making searches more intuitive, and personalizing the booking experience like never before.
How AI is making trip planning easier:
More flexible searches – Instead of clicking through filters, travelers can ask open-ended questions like “Where’s a peaceful beach town to visit in September?” and get tailored recommendations.
AI-powered trip planner – Built in just ten weeks, the AI Trip Planner helps users explore destinations, create itineraries, and check availability—all through a simple chat interface.
Smarter travel matches – AI sorts through reviews, photos, and listings to suggest stays that align with specific preferences, whether it’s “a hotel with a great reading nook” or “a cabin with mountain views.”
Quick answers on demand – Need details on check-in times, parking, or pet policies? AI can provide instant responses, reducing the need to contact customer service.
Concise review summaries – Instead of scrolling through hundreds of reviews, travelers can see key themes like cleanliness, location, and amenities in a quick snapshot.
More efficient host responses – AI-generated message templates help property owners reply faster, making communication between guests and hosts smoother.
Instead of spending hours adjusting filters or scrolling through endless reviews, travelers can just say what they’re looking for and get suggestions that actually make sense. Booking.com has noticed that people are searching in a more natural way, asking open-ended questions and considering a wider range of options before deciding.
AI is helping travelers find what fits without all the extra steps. Rather than clicking through categories, they can describe what they want in their own words and get results that feel relevant. It makes the process feel less like filling out a search form and more like getting recommendations from someone who understands what they need.
In the future, AI could do even more—helping travelers adjust plans on the go, discover unexpected spots, or even rebook flights when things change. Travel comes with surprises, but AI is starting to take some of the stress out of planning, so people can focus on the trip itself.
Read the full article here.
OTHER INTERESTING AI HIGHLIGHTS:
Yahoo’s AI Bet—Can It Reclaim Internet Relevance?
/Steven Levy on WIRED
Once dismissed as a relic of the early internet, Yahoo is making an AI-powered comeback under CEO Jim Lanzone. By shedding money-losing units and strategically acquiring AI-driven tools like Artifact, Yahoo is reinventing its core services, including news, sports, and finance. While it won’t be building its own AI models, Yahoo is integrating AI into its products to boost personalization and user engagement. As the company moves toward an IPO or acquisition, its success will depend on whether AI can help Yahoo reclaim relevance in an industry it once dominated.
Read more here.
MIT and OpenAI Examine ChatGPT’s Role in Emotional Well Being
/Mengying (Cathy) Fang, MIT Media Lab & OpenAI
As AI chatbots become more embedded in daily life, researchers from MIT Media Lab and OpenAI are studying their impact on emotional well-being. Their findings reveal that most users don’t engage with AI in deeply emotional ways, but a small subset of heavy users forms stronger attachments to chatbots like ChatGPT. While AI conversations can provide temporary emotional support, prolonged daily use may have mixed effects on mental health. This study marks an important step in understanding how AI influences human emotions, guiding future AI design for safer, more responsible interactions.
Read more here.
Read OpenAI report here.
Read MIT Media Lab and OpenAI RCT here.
SOME AI TOOLS TO TRY OUT:
That’s a wrap on today’s Almost Daily craziness.
Catch us almost every day—almost! 😉
EXCITING NEWS:
The Another Crazy Day in AI newsletter is on LinkedIn!!!

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