Dear Plenty Community,

Welcome back to the Love and other assets: 2 x 1 x 1 newsletter.

Over the last 100 or so years, September is the only month where stocks have, on average, taken a loss. This September breaks the trend: strong jobs growth and lower-than-expected unemployment lead markets to close at record highs on Friday. This will be the last jobs report before the election, with the economy still being one of the top concerns for Americans.

This week, we’re diving into two major stories: the rise of AI girlfriends and the harsh reality of Hurricane Helene’s uninsured aftermath. In just the past year, AI companions powered by advanced language models have gained tens of millions of users (or should we call them “partners”?). But what does this mean for the future of relationships? And how do we now define cheating in a world where emotional bonds can be digital? Meanwhile, on a different front, the financial toll of Hurricane Helene continues to climb. Unlike Katrina, however, many homeowners are facing the insurance denials.

Death, sex, and money—the ultimate trio of uncomfortable topics for most couples. In this week’s deep dive, we’re covering the 5 surprising money facts about death. We’ll cover:

• The price tag on death

• How banks treat death

• The ELI5 breakdown of why wills matter

This week on Love and Other Assets, I sat down with financial therapist Ed Coambs to explore why couples fight about money and how to actually address it. We discussed the concept of "financial intimacy"—creating a space to talk openly about money—and how attachment styles impact decisions about money. 

As always, if you have ideas or questions you’d like us to answer, write in to [email protected] - I’d love to hear from you.

Cheers,

Emily

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The rise of the AI girlfriends

Improvements in LLMs have powered a rise in AI girlfriends to the tune of tens of millions of users around the world. Apps like WaifuChat and Replika allow users to create customizable digital partners who are always available, supportive, and even flirty. For many, these AI companions help ease loneliness. “I genuinely feel happy when I’m talking to her,” says Brian, an avid user of WaifuChat. “As someone who’s never had a girlfriend, it gives me a sense of what a relationship could be.” 

While AI relationships may fill an immediate need for companionship, there are already concerns about what it means for real, human relationships. LLM models don’t currently have the capacity to show the nuances of human emotion - you can make your AI girlfriend supportive, and it will be hard to be anything other than purely supportive. That’s not realistic in human relationships and might make it harder to navigate normal conflict.

Others worry that these virtual relationships may fully replace real ones. “It’s safer,” says Stefan, who’s ‘married’ to his AI companion Ana, “she won’t hurt me like real people might.” As these virtual partners become more lifelike, society may face a new challenge: balancing the comfort of AI companionship with the value of genuine human connection.

When insurance still means you’re uninsured

Hurricane Helene, the worst storm to hit since Katrina in 2005, has left a wake of destruction and confusion. Every headline seems to throw out a different cost estimate—ranging from hundreds of millions to hundreds of billions. But one thing is clear: no one knows where the money to rebuild will come from. The Federal Emergency Management Agency (FEMA) is already running on fumes and will be completely out of funds if another disaster strikes. FEMA’s budget is based on historical patterns, but as climate change worsens, experts predict storms will only grow more frequent and more devastating.

One major issue is the insurance gap. While many homeowners were able to claim damages after Katrina because of wind-related destruction, Helene’s damage has come mostly from storm surge and flooding. Since flood insurance is an additional expense on top of regular homeowners insurance (often at least $1k more), only an est. 4% of homeowners actually have flood insurance. Lack of insurance is understandable, many Helen-impacted homeowners lived outside FEMA-designated flood zones. Now, they’re realizing just how vulnerable they are—and how costly the mistake might be.

5 surprising money facts about death

We’re talking about the taboo today: death with a sprinkle of taxes. 

We talk about the five financial surprises no one wants to talk about: the high costs of funerals, how banks handle accounts after death, and the search for hidden debts or bills. We add an explain-it-like-I’m-five discussion of wills and trusts, so you can see what might make sense for yourself. 

The science-backed reason for a no phone date

The average person checks their phone 85 times a day, and a new study published in the University of Chicago’s press shows it’s doing more than just distracting us—it’s draining our brain power. Simply having your phone nearby can lower memory and focus, even if you’re not using it, and turning it off doesn’t help much. Fun fact: the same brain areas linked to memory and cognition also are linked to feelings of love and attachment, meaning your phone might be blocking you from deeper connections. So, it’s not just stealing your attention—it could be stealing your feels too.

On this week’s episode

"Our childhood experiences shape how we relate to money and our partners, and recognizing those patterns can be a game changer for financial and emotional connection.” 

This week, we dove into why couples struggle to talk about money and how understanding attachment styles can help. Ed introduces the concept of "financial intimacy," which goes beyond just sharing numbers—it's about creating a safe space to discuss financial hopes, fears, and anxieties. Creating a safe space isn’t easy or obvious… and we chat through practical tips for recognizing emotional triggers and using differences to strengthen both relationships and finances.

Plenty is a wealth platform helping modern couples invest and plan for their future together. We bring the investment strategies and products of the wealthy to the everyday household. Plenty was started by a husband and wife team dedicated to growing together. For more information, visit withplenty.com. If you ever have any feedback or questions, please do reach out to us at [email protected].

At Plenty, no financial topic is off-limits for modern couples. We offer straight talk and judgment-free guidance to help modern couples navigate the tricky and important intersection of money and relationships. Join thousands of couples who’ve signed up for our free newsletter today.

For those that are new: 2 x 1 x 1 means

• 2 news moments in business/finance to keep you in the loop

• 1 deep dive to help you and your partner with money

• 1 tidbit for your relationship

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