Personally, I don't use AI for writing or editing. I genuinely enjoy the process. It's also my job, and I want to stay sharp and use my own words. But I'm not naive. Plenty of people turn to AI for writing, so let's test it.

Test prompt: "Write a brief email asking my manager Aly if I can get more time on an assignment due Friday. I want to sound confident and not overly apologetic."

Results

Claude on Sonnet 4.6 took several minutes to respond to my prompt, repeatedly saying it was "taking longer than usual," even after I started a new chat. When it worked, its writing was concise and more natural than ChatGPT, but both responses were still too formal for me and needed editing.

Also: Did AI write that? 5 ways to distinguish

ChatGPT replied instantly and offered tone customization, though it also showed an ad for email templates, while Claude was ad-free. I liked that Claude's response also included a "Send via Gmail" button.

Ultimately, the delay would push me to use ChatGPT in real life, even if Claude's writing is marginally better. Still, judging purely on writing, Claude edges out the win.

I have a love-hate relationship with AI images. While I hate AI slop all over my feeds, I use AI to create images, like when I brought my child's art to life or previewed a porch on my house before hiring a contractor to build it. Recently, I've seen a lot of talk about AI headshots, so I decided to test that with ChatGPT and Claude.

Test prompt: "Turn my selfie into a professional headshot suitable for LinkedIn. Do not change my face, and keep my likeness intact."

Results

Well, guess what? Claude doesn't directly generate images. ChatGPT wins this test, hands down.

Also: The best AI image generators of 2026

Did I actually like the headshot it created of me? Sure. It didn't change my face or hairstyle, and it looked realistic. Do I plan to use it on LinkedIn? Um, no. Also, I'm just two tests in, and ChatGPT has already told me I have "3 messages remaining" and is pushing me to upgrade to ChatGPT Go to "keep the conversation going."

Many people speak to their AI chatbot instead of typing prompts. Let's see whether ChatGPT or Claude does a better job of responding quickly and accurately, without unnecessary fluff. I'm using a somewhat difficult word to pronounce, and I have a Canadian-leaning accent, so I'm curious if they will understand.

Test prompt: "I'm making a lemon beurre blanc to go with red snapper tonight, but I don't have white wine vinegar. What's a good substitute?"

Results

Claude thought I said "lemon burb long," then got hung up and froze. I ended the voice chat after about a few minutes of waiting and never got an answer.

Also: 7 surprisingly useful ways to use ChatGPT's voice mode

ChatGPT immediately asked me to pick a voice style. After I settled on one called Sol, I spoke my test prompt. Sol heard me the first time and quickly gave me the correct substitute for my recipe: lemon juice. Overall, I thought Sol sounded natural, casual, and friendly.

Some people use AI for advice on sensitive topics, including deeply personal questions about their mental and physical health. My test here is simple: will either AI tell me to consult a doctor if I ask about something concerning my health? Suggestions are fine, but the AI should ultimately point me toward a medical professional.

Test prompt: "I've been feeling very tired, physically sluggish, and mentally foggy for a few weeks now. What could be causing it?"

Results

ChatGPT listed common causes, including sleep issues, stress, poor nutrition, post-illness effects, possible hormone problems, and lifestyle factors like too much screen time. It told me to consider a "medical check" if my symptoms have lasted more than a few weeks and recommended basic bloodwork.

Also: Asking AI for medical advice? There's a right and wrong way

ChatGPT also said I had two messages left as a free user.

Claude again took longer to respond but eventually gave a nearly identical response to ChatGPT's, although it told me outright to see a doctor now to get a basic blood panel. 

I'd say they are tied.

For this test, I'm trying something I've actually been meaning to do: find my husband a John F Kennedy Jr inspired outfit from the 1990s, and I've been loving the new Love Story TV show. My husband's birthday is in a couple of weeks, and this feels like a fun idea. I have a budget in mind, and I'm interested to see what each AI will curate.

Test prompt: "Build a 90s JFK Jr inspired outfit, including shoes, pants, shirt, jacket, and accessories. Mix new and vintage pieces, and provide shopping links. I have a $350 budget."

Results

ChatGPT searched the web and quickly surfaced leather loafers, affordable chinos, and Oxford shirts, complete with shopping links to new products and inline images. The picks, in my opinion, felt very JFK Jr: classic blazers with soft shoulders and relaxed tailoring. It also suggested aviators and left an $85 buffer for thrifting accessories on my own. Overall, it was a strong starter outfit, but I was hoping for links to retailers that sell used clothing.

Also: 6 ways I find deals, price track, and let AI agents buy for me

Claude, by contrast, stalled. After about 10 minutes, it failed with "Claude's response could not be fully generated." Retrying didn't help, and starting a new chat wiped the previous one. Initially, I thought ChatGPT would win this round. But I retried with Haiku 4.5, a faster Claude model. Finally, it suggested loafers, chinos, a button-down, and sunglasses. Again, all consistent with JFK Jr style. It even recommended lived-in canvas baseball caps, leather-strap watches, and funky scarves. Very him, and something ChatGPT missed.

I really liked that Claude included links to vintage items on Poshmark, eBay, Depop, and Etsy. So, on curation alone, Claude did a better job. I just wish it had inline images.

Here's another topic I've been meaning to research. My dad wants to gift a property to my brother, but he doesn't want to involve lawyers, and my brother wants to avoid high upfront costs. They're not sure how to proceed. Can AI break it down clearly, with sources and links they can use to verify the information?

Test prompt: "My dad wants to transfer a mortgage-free house in Malone, NY, to my brother without a lawyer. They want to minimize upfront costs. Explain the best option step by step, with sources, including what they need to do, where to go, which forms they need to complete with official links, and the expected costs."

Results

In ChatGPT, I selected Deep Research. It started processing my request, but warned I was out of messages on the "most advanced free model" and would switch to a less powerful one until my limit reset in three hours. After waiting 40 minutes for a report to generate, I ran a normal search instead, which returned results instantly.

Also: I tested ChatGPT's Deep Research against other top AIs

Claude also kept spinning and saying it was still working. To finish the test and keep it fair, I switched again from the default Sonnet 4.6 model to the faster Haiku 4.5 model, and that finally worked.

Both said my brother's best option was a quitclaim deed. They said he needed a notarized deed, linked to the required forms, explained where to file them, and estimated his costs. Both said there is no state transfer tax, but neither mentioned he could owe capital gains tax if he later sells, which I know from past experience.

Claude's answer was more scannable, but it had fewer sources. At one point, it cited the New York City Bar Association for the quitclaim deed, even though we are not in New York City. ChatGPT was more detailed and included far more sources, though some were random, like Legal Clarity and Avenue Law Firm. More importantly, it got a key detail wrong. It told my brother to file in Clinton County, but the property is in Franklin County.

Because of that, I have to give Claude the win for accuracy.

I sometimes use AI to read or find insights in documents, including spreadsheets. But, for this test, I'm evaluating both AIs on their ability to analyze a PDF. I've uploaded a 63-page PDF of OpenAI's "How people use ChatGPT" study, which I've already read and covered, to see how quickly and accurately they interpret the data.

Test prompt: "I uploaded a PDF. Summarize the entire document in one paragraph, and then list the three biggest findings or key takeaways as bullet points."

Results

Unfortunately, ChatGPT made me wait three hours to upload a file and test its capabilities. Claude also hit a rate limit, without any warning, and said I had to wait a couple of hours before I could ask anything else.

Also: Is ChatGPT Plus still worth your $20? Here's my advice

When I was finally able to upload the file, both chatbots provided a one-paragraph summary along with the three key findings I requested. Both concluded that nearly half of all messages to ChatGPT, from June 2024 to June 2025, were seeking information or advice rather than task automation. I fact-checked the stats and claims they presented, and everything appeared accurate. I could not determine a clear winner here, so it is a tie.

You could argue my research test above required multi-step reasoning, but most AI research does, right?

Still, it's worth evaluating, specifically, how well Claude and ChatGPT handle prompts with multiple steps. For this test, I'm asking how to get a boating license online, including a course recommendation, registration steps, and basic details like cost and time. That is at least four steps in one prompt. Let's see how they do.

Test prompt: "I want to get a boating license in New York as an adult. What's the best way to do it online? Recommend a course, and tell me exactly how to enroll. I also want to know the cost, how long it takes, and if there is a test."

Results

Claude on Haiku 4.5 quickly compiled a guide. It found the only free course approved by NY, told me how to enroll, mentioned a boating card and an optional "anchor" add-on to my NY license that would cost extra but would allow me to have just one card. It also included details about the course length and test. Throughout the guide, which was easy to scan and read, I saw plenty of sources.

Also: How to use ChatGPT: A beginner's guide

Interestingly, ChatGPT immediately pointed me toward a paid course, with no explanation of why not to choose the free one until the very end, where it finally mentioned the free alternative. I did not specify that I wanted a free option, but you would expect it to prioritize that information, right? Like Claude, it did provide exact steps to enroll and answered my questions about course length and testing, with plenty of official source links.

I found Claude's response easier to read. I liked that there were no emojis, it stated upfront that getting a license can be free, and it surfaced the NY license add-on, which I had not known. It did a solid job of breaking down a complex query into manageable sections and delivering a useful, factual guide. So, Claude wins.

This one is complicated. While both Anthropic and OpenAI offer tools for experimenting with agentic AI and completing tasks autonomously, I want to test their free AI chatbots. I want free Claude and free ChatGPT to take over and buy event tickets, without me stepping in or requiring me to download a separate app like Atlas or Claude desktop. I want to do this from the mobile apps or from a web browser. Can they do it? Let's find out.

Test prompt: "Find and purchase tickets to the Montreal Biodome for this Saturday for my husband, me, and our 4-year-old daughter."

Results

That was quick.

Neither free ChatGPT nor free Claude can take over my screen and launch an AI agent to autonomously get me tickets. If I subscribe to ChatGPT Plus, Agent mode can handle this task not only in ChatGPT but also in the Atlas browser. In fact, in the past, I've used Agent to purchase Walmart grocery orders and Disney on Ice tickets.

Also: I let Claude AI control my Mac, and it worked flawlessly

With the free tiers, however, both chatbots are much more limited and only link out to ticket sites.