Business
The people turning to AI for dating and relationship advice
Suzanne BearneTechnology Reporter
Getty ImagesEarlier this year, Rachel wanted to clear the air with a man she had been dating before seeing him again in a wider friendship group setting.
“I’d used ChatGPT for job searching but had heard someone else use it [for dating advice],” says Rachel, who does not want her real name used, and lives in Sheffield.
“I was feeling quite distressed and wanted guidance, and didn’t want friends involved.”
Before the phone call, she turned to ChatGPT for help. “I asked, how do I deal with this conversation but not be on the defensive.”
Its response?
“ChatGPT does this all the time but it was something like ‘wow, that’s such a self-aware question, you must be emotionally mature going through this. Here are some tips’. It was like a cheerleader on my side, like I was right and he was wrong.”
Overall, she says it was “useful” but described the language as “very much like therapy speak, using words like ‘boundaries'”.
“All I took from it was it reminded me to be OK to do it on my terms, but I didn’t take it too literally.”
Rachel is not alone in turning to AI for advice in dealing with relationships.
According to research by the online dating firm Match, almost half of Generation Z Americans (those born between 1997 and 2012) said they have used LLMs like ChatGPT for dating advice, that’s more than any other generation.
People are turning to AI to help craft breakup messages, to dissect conversations they’re having with people they’re dating, and to resolve problems in relationships.
Anastasia JobsonDr Lalitaa Suglani, psychologist and relationship expert, says AI can be a useful tool, especially for people who feel overwhelmed or unsure when it comes to communication in relationships.
It may help them to craft a text, process a confusing message or source a second opinion, which can offer a moment of pause instead of being reactive, she says.
“In many ways it can function like a journalling prompt or reflective space, which can be supportive when used as a tool and not a replacement for connection,” says Dr Suglani.
However, she flags several concerns.
“LLMs are trained to be helpful and agreeable and repeat back what you are sharing, so they may subtly validate dysfunctional patterns or echo back assumptions, especially if the prompt is biased and the problem with this it can reinforce distorted narratives or avoidance tendencies.”
For example, she says, using AI to write a breakup text might be a way to avoid the discomfort of the situation. That might contribute to avoidant behaviours, as the individual is not sitting with how they actually feel.
Using AI might also inhibit their own development.
“If someone turns to an LLM every time they’re unsure how to respond or feel emotionally exposed, they might start outsourcing their intuition, emotional language, and sense of relational self,” says Dr Suglani.
She also notes that AI messages can be emotionally sterile and make communication feel scripted, which can be unnerving to receive.
Es LeeDespite the challenges, services are springing up to serve the market for relationship advice.
Mei is a free AI generated service. Trained using Open AI, the service responds to relationship dilemmas with conversational-like responses.
“The idea is to allow people to instantly seek help to navigate relationships because not everyone can talk to friends or family for fear of judgment,” says New York-based founder Es Lee.
He says more than half of the issues brought up on the AI tool concern sex, a subject that many may not wish to discuss with friends or a therapist, Mr Lee says.
“People are only using AI as existing services are lacking,” he says.
Another common use is how to reword a message or how to fix an issue in a relationship. “It’s like people need AI to validate it [the problem].”
When giving relationship advice, issues of safety could come up. A human counsellor would know when to intervene and protect a client from a potentially harmful situation.
Would a relationship app provide the same guardrails?
Mr Lee recognises the concern over safety. “I think the stakes are higher with AI because it can connect with us on a personal level the way no other technology has.”
But he says Mei has “guardrails” built into the AI.
“We welcome professionals and organisations to partner with us and take an active role in molding our AI products,” he says.
OpenAI the creator of ChatGPT says that its latest model has shown improvements in areas like avoiding unhealthy levels of emotional reliance and sycophancy.
In a statement the company said:
“People sometimes turn to ChatGPT in sensitive moments, so we want to make sure it responds appropriately, guided by experts. This includes directing people to professional help when appropriate, strengthening our safeguards in how our models respond to sensitive requests and nudging for breaks during long sessions.”
Another area of concern is privacy. Such apps could potentially collect very sensitive data, which could be devastating if exposed by hackers.
Mr Lee says “at every fork in the road on how we handle user privacy, we choose the one that preserves privacy and collects only what we need to provide the best service.”
As part of that policy, he says that Mei does not ask for information that would identify an individual, other than an email address.
Mr Lee also says conversations are saved temporarily for quality assurance but discarded after 30 days. “They are not currently saved permanently to any database.”
Some people are using AI in combination with a human therapist.
When Corinne (not her real name) was looking to end a relationship late last year, she started to turn to ChatGPT for advice on how to deal with it.
London-based Corinne says she was inspired to turn to AI after hearing her housemate talk positively about using it for dating advice, including how to break up with someone.
She said she would ask it to respond to her questions in the same style as popular relationship expert Jillian Turecki or holistic psychologist Dr Nicole LePera, both very popular on social media.
When she started dating again at the start of the year she turned to it again, again asking for advice in the style of her favourite relationship experts.
“Around January I had been on a date with a guy and I didn’t find him physically attractive but we get on really well so I asked it if it was worth going on another date. I knew they would say yes as I read their books but it was nice to have the advice tailored to my scenario.”
Corinne, who has a therapist, says the discussions with her therapist delve more into childhood than the questions she raises with ChatGPT over dating or relationship queries.
She says that she treats AI advice with “a bit of distance”.
“I can imagine people ending relationships and perhaps having conversations they shouldn’t be having yet [with their partner] as ChatGPT just repeats back what it thinks you want to hear.
“It’s good in life’s stressful moments. And when a friend isn’t around. It calms me down.”
Business
Lawsuit over $21 million donor-advised fund highlights risks of DAF giving
Ridvan_celik | Istock | Getty Images
A version of this article first appeared in CNBC’s Inside Wealth newsletter with Robert Frank, a weekly guide to the high-net-worth investor and consumer. Sign up to receive future editions, straight to your inbox.
With donor-advised funds gaining popularity as a vehicle for the wealthy to give back, risks and potential conflicts of interests are emerging — and being put on display in a lawsuit over a family’s $21 million charitable fund.
Philip Peterson, a 63-year-old Kansas resident, filed suit in January alleging that the nonprofit that administers his family’s donor-advised fund has refused to communicate with him and has failed to make charitable grants that he has recommended since early 2024. The suit, filed in Colorado federal court, alleges the Christian nonprofit, called WaterStone, cut off his access to information about the account and that he doesn’t know how the fund has fared since the end of 2023, when it had $21 million in assets.
Counsel for WaterStone, founded as the Christian Community Foundation, said in a statement that the Colorado Springs nonprofit has respected the wishes of Peterson’s late father, who originally created the fund in 2005 and died in 2019.
The case sheds light on the growing uptake, and dangers, of donor-advised funds, or DAFs, which have quickly become one of the most dominant forces in philanthropy. Americans donated nearly $90 billion to DAFs in 2024, per the most recent annual report from the DAF Research Collaborative. According to the most recent data available, DAFs held $326 billion combined in assets in 2024.
For Americans looking to give back and save on taxes, DAFs are marketed as a flexible and simple way to do so, often described as charitable saving accounts or credit cards. Instead of writing a check to a nonprofit, donors contribute cash and other assets to a DAF. While the tax deduction is immediate, the funds can be allocated to charities later.
DAFs, unlike private foundations, are not required to distribute assets within a given timeframe, a common criticism among opponents who say DAFs are wealth hoarding vehicles.
The Peterson case offers a cautionary tale on the tradeoffs – especially when it comes to control. While donors are able to recommend how the funds are distributed to charity, the assets are legally controlled by the organizations that administer the DAF on their behalf. Though these organizations, also known as sponsors, typically respect their donors’ wishes, donors have little recourse if they do not.
“It’s sold to the public as, ‘This is your account, and you can decide where it goes, and you can move it, and you maintain full control.’ But if you don’t give up dominion and control, you don’t get the tax benefits,” said Ray Madoff, tax scholar and professor at Boston College Law School. “There’s a disconnect between the legal rules that govern it and the understanding of the parties. And this case is a perfect example of it.”
How much to give
Peterson told Inside Wealth that the rift with WaterStone started with a disagreement over how much to distribute.
In early 2024, Peterson alleges, WaterStone CEO Ken Harrison told him that the organization was going to keep the fund’s principal in perpetuity and only make grants from investment income. Peterson said he did not agree to the proposal as this would not allow the fund to make its customary annual grants of between $2.3 million and $2.5 million.
He further alleges that in March 2024, after he told Harrison over Zoom that he wanted to move the DAF to another sponsor, Harrison told him never to contact WaterStone again and abruptly ended the call.
Now Peterson is suing to assert his advisory privileges and regain access to the DAF, which was started by his late father, Gordon Peterson, a real estate investor and devout Christian, to support evangelical Christian causes. Peterson ultimately seeks the court to compel WaterStone to transfer the DAF to another organization so he can bring the fund’s giving back up to speed.
He said he requested WaterStone make a $1 million grant in 2024 but does not know if that grant – or if any grants – were issued that year. In 2025, WaterStone notified Peterson it would permit a $400,000 distribution from the fund, he said.
“I made a promise to my father. I promised him that if I was the remaining person on the account that I would direct the funds as I knew that he would 100% approve,” he said. “I want to be a man of my word.”
Philip Peterson, left, pictured with his father Gordon in 2015. Gordon Peterson passed away in 2019.
Courtesy of Philip Peterson
WaterStone declined to comment on specifics of Peterson’s allegations. The deadline for WaterStone to answer the complaint in court or move to dismiss it is mid-March.
“WaterStone has consistently carried out the articulated wishes of the donor since the donor advised fund in question was established,” WaterStone’s legal counsel said in a written statement, referring to Peterson’s father. “The plaintiff in this case is not the donor.”
Andrew Nussbaum, Peterson’s lawyer, said that WaterStone helped Gordon Peterson appoint his wife, Ruth, and son Philip as co-advisors to the DAF before he died. Ruth Peterson died in 2021, leaving Philip Peterson as the sole successor-advisor. Prior to 2024, WaterStone granted Philip Peterson’s grant requests, Nussbaum said.
Nussbaum said the lawsuit could set a chilling precedent if the court upholds WaterStone’s argument that designated successors do not have advisory privileges.
“If WaterStone is right, you’re talking about billions of dollars being beyond any kind of legal reach of the original donor-advisors or their successors to have any oversight related to the funds,” Nussbaum said.
Moreover, Peterson said he believes WaterStone has not honored his father’s wishes. He alleges that WaterStone has delayed or denied his grant recommendations even though they met the mission statement written by his father, which included a list of approved charities.
“I can tell you this: My dad would never have created a donor-advised fund if he knew that this was going to be the outcome. He felt very passionately about this,” he said.
DAF trade-offs
Law professor and DAF critic Roger Colinvaux said in his view, donors who want control of DAF assets are trying to have their cake and eat it too.
“Whether you like DAFs or not, the DAF sponsor is an independent charity. It’s an independent entity, and its duties are not to the donor,” said Colinvaux, professor at the Columbus School of Law at the Catholic University of America. “If the plaintiff wanted the sort of control that the plaintiff seems to want, as evidenced in the complaint, there’s a structure for that, and that’s a private foundation.”
Dana Brakman Reiser, professor at Brooklyn Law School, cautioned that Peterson’s story is a rare scenario. She said the biggest DAF sponsors like Fidelity Charitable and Schwab Charitable (now DAFgiving360) are affiliated with financial institutions and generally inclined to keep donors happy.
“It’s in their interest as long as honoring the donor’s request is not going to get the sponsor in trouble,” she said. Brakman Reiser added that the IRS prohibits using DAF assets to buy gala tickets or pay college tuition.
Still, the interests of sponsors and donor-advisors are rarely perfectly aligned.
Sponsors typically collect fees for managing DAF assets, creating an inherent financial incentive to disburse fewer assets, according to Chuck Collins, the director of the Program on Inequality and the Common Good at the Institute for Policy Studies, a progressive think tank. While community foundations pioneered the DAF model, they are now competing with larger commercially-affiliated sponsors for donors’ dollars, he added.
“More and more, they are having to compete with the commercial DAFs like Fidelity that have very low overhead and don’t take much in the way of fees. And so what’s the business model for a community foundation where, you know, 80% of the donations coming in are from people wanting to create DAFs?” he said. “In reality, their business model now depends on people parking their assets for longer periods of time.”
While Peterson’s case is unusual, it’s not the first legal challenge surrounding DAFs.
In 2018, a hedge fund couple sued Fidelity Charitable, contending the sponsor broke an agreement to liquidate their donated shares gradually and instead sold off 1.93 million shares, a position originally worth $100 million, in a matter of hours. Fidelity Charitable argued that it had followed the law and the case was ruled in their favor.
In another noteworthy debacle, in 2009, a Virginia-based charity called the National Heritage Foundation wiped out 9,000 DAFs worth $25 million combined to pay out creditors after it filed for bankruptcy.
Giving directly to charity doesn’t necessarily guarantee the assets will be used to the donor’s intent. But adding an intermediary into the equation adds another layer of complexity.
The handful of lawsuits filed by donor-advisors over how DAF assets are spent or invested have thus far been largely unsuccessful in court.
In short, according to Colinvaux, courts have upheld that donors have ceded any control in order to qualify for the tax break. If donors had the right to control assets — as opposed to the privilege to advise — they would not be able to claim a deduction, he said.
Nussbaum said Peterson’s case is different as it focuses on his rights to advise grants rather than control over how the assets are investments.
Peterson said he tried to resolve the dispute with Waterstone for about two years before going to court. While he knows his suit faces considerable odds, he said he felt he had no choice.
“People put an enormous amount of trust in these companies, and we’re hopefully going to find out what these companies can and can’t do,” he said. “It may have a big effect on the industry, and I don’t want to be that guy. All I want to do is to be able to continue my father’s legacy.”
Correction: This story has been updated to correct the IRS limitations on use of DAF assets.
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