In August, I quit my steady job as a New York City public high school teacher to start a full-time graduate program in Manhattan. I worried about the choice not only because I loved my work with the kids, but also because I had traded a consistent paycheck and affordable health insurance for tens of thousands of dollars in tuition.
When I was teaching, I prepared for the cost by scrimping to save every cent I could. But my account balance still wouldn’t fully cover two years of school and living expenses.
Throughout my savings journey, I learned a lot of lessons, especially from my older friends.
I jumped into major money-saving mode
As a result, I redoubled my frugal efforts. I made a rule that I wouldn’t eat out or order takeout unless it was someone’s birthday. I asked to meet people in parks rather than restaurants and suggested $5 happy-hour spots from a meticulously crafted list on my phone.
On rare occasions when I dined out, I looked at the prices before deciding what to order and pored over the bill with a calculator.
It worked. While it was still difficult to watch my savings dwindle — buoyed occasionally by small deposits from part-time jobs — I kept my costs (relatively) low for a 20-something in the city. Most friends understood my restrictions or were in similar situations.
I worried when my older friends routinely paid for me
But this approach didn’t work as well with my five older friends from my intergenerational writer’s group. We’d been meeting weekly on Zoom for several years when we started visiting each other in our home states across the country. As women in their 40s and 60s in dual-income households with established careers, they understandably gravitated toward nicer places where the cheapest cocktail cost $20. My dive bars with weirdly stained walls weren’t going to cut it.
When I visited two of these friends in Chicago, I anticipated that we’d go to swanky spots and saved up for weeks, cutting out anything nonessential from my grocery list — chocolate-covered pretzels, bananas, frozen fried rice.
But when I offered to chip in for our multi-course dinners or luxury spa day, they brushed me off.
I was grateful for their generosity, yet overcome with guilt. They had contributed so much to our time together. I didn’t want to be a freeloader, the friend who couldn’t hold up her end of the deal. How could I pay them back and show my appreciation?
At the end of the trip, my friend Andrea, 46, and I ate lunch in a diner in the Gold Coast. I made one last offer to Zelle her. In response, she said something that stuck with me.
“When I was in my 20s, people helped me,” she told me with an easy smile. “When you’re 40, just pay it forward by buying a younger woman dinner.”
Her wisdom helped me slowly release my anxiety
I mulled over her words on the plane home. I was surprised that her view of the situation differed so much from mine, and relieved she didn’t see me as taking advantage of her. Yet it was still hard to fully let go of the weight in my chest — the feeling of being indebted to someone’s kindness, of accepting a gift while knowing you can’t reciprocate.
Months later, my 64-year-old friend from my writer’s group visited from Florida. We went out for coffee, and I thought to myself, Okay, now this I can afford. But when I offered to cover or at least split it, she waved me off, saying, “My treat.”
I thought of Andrea’s words and told myself, She’s being nice. Don’t worry about it.
“Thank you,” I said, and meant it.
A while later, when another friend visited from Washington, she paid most of our checks at the bars and restaurants we visited. Though I felt a twinge of the usual panic at first, by our second day together, I was able to let it go. As we wandered through the Upper West Side, the tightness in my chest lifted, leaving only gratitude that she was here.
I do plan on paying it forward
Andrea was right, I realized. Helping each other was what friends did, and they clearly weren’t bothered by it. Sure, I wasn’t paying for lavish things or hosting people, but I shouldn’t let my own hangups affect our time together, which always produces some of my favorite memories.
Eventually, I’ll be able to do what they’ve done for me for another woman, who can then help someone else.
Instead of worrying, now I let my friends’ kindness bring us together and smile, knowing that every time I pay for a 20-something woman in the future, I’ll think of them.
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