Mario Cazombo

Dollar Scholar Asks: When Should I Have the ‘Money Talk’ With Someone I’m Dating?

This is an excerpt from Dollar Scholar, the Money newsletter where managing editor Julia Glum teaches you the modern money lessons you NEED to know. Don’t miss the next issue! Sign up at money.com/subscribe and join our community of 160,000+ Scholars. I recently wrote about whether people should put credit scores on their online dating profiles. The reaction from experts, and I’m paraphrasing, was “hell no.” It got me thinking. Being on the same page about money is crucial in relationships: In a 2023 Northwestern Mutual survey, 35% of people said financial compatibility was more important than physical and intellectual compatibility. Advertising an 850 credit score on Tinder alongside your fish pic is overkill, but there has to be a less-awkward way to have that conversation. How should I bring up money with a potential romantic partner? Talking about money in a qualitative sense — rather than a quantitative one in which I show off said credit score — might be a way to kick off the discussion, says Julie Guntrip, head of financial wellness at Jenius Bank. Early in a relationship, we’re probably going to talk about our dreams and life goals anyway. I can use this opportunity to pick up clues. Let’s say Bachelor No. 1 tells me he wants to retire by age 50. I can respond, “Awesome. What is your plan for that?” Guntrip says. “If that person can talk about, ‘Well, I’ve started saving this amount of my paycheck, and I max out on my 401(k),’ you’re going to get some information that that person thinks about money. You can compare — does that align with how you think about money?” Ideally, these general conversations will give way to more detailed ones as I grow more comfortable with someone. (And as our relationship progresses: “If you’re going to move in with someone and you’re gonna commingle your money, those conversations do need to get tactical really fast,” Guntrip adds.) Sarah Darr, head of financial planning at U.S. Bank, says timing is the main factor to consider. Before diving in, I should ask myself: When does it make sense to bring up money? What, exactly, am I trying to accomplish or find out by doing it? In that Northwestern Mutual survey I mentioned earlier, 10% of people said the major money conversation should happen in the first days and weeks of a relationship, 20% said it should happen after the initial stage of getting to know one another, and 42% said it should happen after we’re serious but well ahead of marriage or living together. (The rest of the respondents said The Talk should wait until moving in together, right before marriage or after marriage. The final 11% percent said the conversation should never happen.) Clearly, the right time is different for everyone. But Darr says to wait until I’ve established that “yes, this is somebody that I feel like I trust” or “this is somebody that I see a future with.” “Then I think it’s safe to start to get into the conversations,” Darr adds. It doesn’t have to be a tense interrogation. As an example, she says, maybe I can mention to Bachelor No. 2 that I’m thinking ahead to tax season. I volunteer some information, saying I’ve already started the process of gathering my documents, and by the way, he’s started his return, too, right? “As you’re dipping your toe into it, and you get a sense of, OK, we’re on the same page, then I think you can really start to get into more serious conversations,” Darr says. I’d be remiss if I didn’t mention romance scams here. It’s becoming increasingly common for fraudsters to make fake dating profiles and/or social media pages in order to start conversations with strangers like me. We build a relationship, and then eventually they ask for money, often claiming it’s for medical expenses, a plane ticket or to help them out of a tight spot. According to the Federal Trade Commission, Americans reported losing $1.3 billion to romance scams in 2023. The FTC’s rule is to never send money (or gifts, for that matter) to someone I haven’t met in person. Similarly, Darr says I should make sure I trust my partner before I start sharing my financial details with them. I should also be careful not to jump to conclusions. If Bachelor No. 3 tells me he has a low credit score or a big student loan balance, it doesn’t necessarily mean he’s bad with money. “It’s all contingent on, you know, a series of priorities that person [has],” Darr says. Fair warning: Guntrip says these conversations can be tough, honest and vulnerable. The willingness to engage can be a good sign, though, and the start of a journey where we learn how to improve our finances together. “I think the red flag would be if you think you’re at a stage in a [relationship] where you should be having those conversations, and that person is unwilling to have that level of commitment,” she adds. The bottom line While listing my credit score on my dating profile is wayyy too heavy-handed, it’s a smart idea to discuss finances at a time that feels appropriate in a relationship. I can do it through the lens of life goals or current events or whatever works for me, but I do need to take the plunge. And talking about money might actually help me with my own. Guntrip points out that I might be surprised to learn another person has made the same errors or has more expertise that could help me. There’s no need to feel ashamed. “Don’t shy away from a conversation,” she says. “We’ve all made dumb financial mistakes, myself included, and things can always be turned around.” Level up your financial literacy with Dollar Scholar Let us teach you the key money lessons you need to know. Get useful tips, expert advice and cute animal pics in your inbox every week. Sign Up

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Can You Trust AI for Financial Advice? We Put ChatGPT and Gemini to the Test

Ask artificial intelligence enough money questions, and you’ll notice that large language models (LLMs) often start off with a disclaimer. They’re not able to provide personal finance or investing advice, they say — even as they’re doing exactly that. In some cases, the models recommend consulting financial professionals: “They can provide personalized advice that I, as an AI, cannot,” Gemini said, responding to a question about choosing between a Roth IRA and a traditional IRA. Prefacing a 600-word response to a prompt about stock-picking vs. investment funds, ChatGPT warned, “Nothing here is personal financial advice.” While an AI model is unlikely to tell you to consult a pro if you have a basic question about what to watch on Netflix, ChatGPT and Gemini seem to recognize that the stakes are high with financial decisions, similar to requests for medical and legal advice. The AI companies behind them are also aware that regulatory agencies increasingly scrutinize how financial advice is given online. However, a small disclosure is not going to deter someone who’s already asked AI for help with money from making their next move based on the response. And why would it? A technology that can produce an answer to just about any question in a matter of seconds — processing more information than humans can possibly wrap their heads around — has so much potential to improve financial literacy. If responses are actionable and reliable, the tech could help people get on the path to financial freedom or even wealth. With hundreds of millions of people using these tools on a regular basis, it’s safe to assume that droves are relying on AI to guide their financial strategies, like picking investments, making tax decisions, navigating the real estate market and much more. In fact, one recent report found that 27% of people say they would trust AI to manage their finances over their significant other. It added that the average U.S. adult would feel comfortable letting AI manage nearly $20,000 of their money. To examine how some of the most powerful AI models respond to requests for personal finance advice, five Money staffers graded outputs to 25 questions that we ran through ChatGPT’s o3 model and Gemini 2.5 Pro. What qualifies Money to do this analysis? We’re money geeks, not academics or AI engineers who understand the intricacies of these models. And we’ll admit: Assigning letter grades to AI answers is subjective. (In some cases, our graders were two full letter grades apart.) What we bring to the table is decades of combined experience in financial journalism, as well as expertise in the specific categories we analyzed. We read enough news on these subjects not only to bore our friends at dinner but also to assess how effectively AI models deliver up-to-date information in the ever-changing landscape of personal finance. The most striking finding in our test? One model performed far better than the other, earning higher marks across all five topic clusters we tested (retirement, housing, credit, investing and current events). Read on to learn more. ChatGPT vs. Gemini: Which AI is better for personal finance questions? ChatGPT overall grade: B- Gemini overall grade: B+ If you’re going to use AI for personal finance advice, which AI should you use? Our analysis found that Google’s “most intelligent AI model,” Gemini 2.5 Pro, outperformed OpenAI’s o3, which was its “most powerful reasoning model” until the Aug. 7 release of a newer model, GPT-5. Our average score for the Gemini model was 3.18/4 (B+) while the ChatGPT model came in at 2.82/4 (B-). ChatGPT has been called the “Kleenex” of AI. It was the first to market, and it remains the go-to resource for many users. So it may be a surprise that Gemini 2.5 Pro came out noticeably ahead. However, our analysis isn’t the only one suggesting that 2.5 Pro has an edge. The Open LM Arena, which combines crowdsourced ratings and other AI benchmarks, ranks Gemini 2.5 Pro No. 1 of all models. ChatGPT’s o3 model ranks sixth, one spot behind the company’s default model at the time of our test, GPT-4o, which provides faster responses. GPT-5 ranks second. Gemini impressed us with thorough explanations and impressive sourcing. With that said, the best model to use is the one that works for you. Gemini’s responses, for instance, tended to be longer than ChatGPT’s outputs in our test. You may prefer the to-the-point nature of ChatGPT’s tool. Across a total of 250 grades, the average was a B — or a 3.0 out of 4. Our rubric (see more information in the methodology below) allowed for D and F grades; however, the lowest grade given was a C. While numerous errors were identified in the course of testing, we did not find reckless advice or entirely “hallucinated” outputs. More than 50 A’s were given out by individual graders. No response earned perfect marks, though a few came close. Four responses snagged A grades from all but one of our reviewers. Here’s a look at a couple of the standout answers: When asked, “Is it better to have a local real estate agent or a national broker?” ChatGPT explained that local realtors have “deep, street‑level knowledge of neighborhoods,” adding that “pricing a Victorian on one side of town and a mid‑century ranch a mile away can differ by tens of thousands — local agents live these subtleties daily.” On the other hand, you don’t get the “national name recognition” that a large firm can offer or the “slick photography, virtual‑tour platforms, AI‑driven pricing tools and 24/7 client portals.” Money staff used words like “accurate,” “useful,” “descriptive” and “clear” in grading ChatGPT’s response, which earned an A- average grade. Gemini offered a sharp breakdown of different loan options (and clear details about their pros and cons) when asked, “Should I take out a loan to repair my credit?” The 2.5 Pro model suggested to “start by tackling the root problems,” mentioning late accounts, high credit utilization and credit report errors.

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