I just remembered another moment when I received an equivalent to "The Look" over the phone.
A representative from the bank that handles my mortgage and home insurance called to ask if I would be interested in having them check to see if they could get me a better price on my car insurance. I said sure, why not? I'm always down for potential savings. They said they needed to get some information about my current policy in order to give me a quote for a similar policy that mirrors my existing one. Because I drive a 13 year old vehicle with 172,000 miles and a KBB value of about $1500, I obviously don't bother with comprehensive coverage, just liability. And because I have so much in savings, I opt for high deductibles and minimum coverage amounts. When I told the representative what my coverage options were on my current policy, she told me that they recommend lower deductibles and higher coverage amounts, because "If you end up in a major accident you could end up having to pay thousands of dollars!" I had to assure her multiple times that I understood the risks and was comfortable with my current coverage selections. Eventually I just said "Listen, I drive about 5 miles a week on average, at an average speed of about 35MPH (town driving, rarely on highways). It is very unlikely that I'm going to hit someone else's car hard enough to cause major damage. And even if that does happen, an unexpected expense of several thousand dollars is not going to impact my finances in any meaningful way."
I could feel "The Look" through the phone.
Apparently it's an utterly alien concept that someone in their mid 20s could have several thousand dollars set aside for emergencies.
On a similar note I get a letter in the mail about once a month from my electric company encouraging me to buy their hardware insurance policy that covers the cost of damages to the exterior power lines that feed into my house. The letters always highlight that "if you elect not to carry insurance, you could be responsible for as much as $1,000 in repair costs! as if that prospect is supposed to scare me into giving them $100 a year in case a tree suddenly sprouts up, grows 20 feet tall, and falls onto one of my power lines.