I'm 44 and I just realized the reason I always buy the second-cheapest wine at restaurants isn't because I prefer it — it's because ordering the cheapest feels shameful and ordering anything above that feels like I'm pretending to be someone I'm not

Last week at a small Italian place in Silver Lake, I caught myself doing it again. The server handed me the wine list, and my eyes automatically skipped past the house red at $28, landed on the $35 Chianti, and stayed there. Not because I particularly wanted it. Not because I knew anything about that specific vineyard. But because it wasn't the cheapest option.

I've been doing this dance for over two decades, and only now am I starting to understand what's really happening.

It hit me like a revelation sitting there, waiting for my vegan arrabbiata. This wasn't about wine preferences or sophisticated taste. This was about the stories I've been telling myself about money, worth, and who I'm allowed to be in public spaces.

The psychology of the middle ground

Think about your own restaurant habits for a moment. Do you genuinely order what you want, or do you order what feels socially acceptable?

Behavioral economists have a name for this: the compromise effect. When given three options, we tend to avoid the extremes and pick the middle one. It feels safer, more reasonable. But here's what fascinated me when I dug deeper - this isn't just about rational decision-making. It's about social signaling and deeply embedded shame around money.

The second-cheapest option has become my armor. It protects me from two equally uncomfortable identities: the person who can't afford better, and the person who thinks they deserve luxury.

Growing up in suburban Sacramento, money was always this weird, unspoken thing. My grandmother raised four kids on a teacher's salary, and even now, in her eighties, she still volunteers at the food bank every Saturday. She taught me the value of a dollar, but somewhere along the way, I also learned that spending money on yourself was somehow selfish or showy.

When frugality becomes performance

Here's the thing nobody talks about: sometimes being frugal is just another kind of performance. We're not actually saving money for any particular goal. We're performing humility, performing relatability, performing "I'm not one of those people."

But who are "those people" exactly? And why am I so afraid of being mistaken for them?

I've mentioned this before, but our spending habits reveal more about our internal narratives than our actual financial situation. I can afford the $55 wine. Hell, I could probably afford the $75 one if I really wanted it. But there's this invisible barrier, this voice that says, "That's not for people like you."

The irony? I'll drop $200 on books without blinking. I'll invest in a new camera lens or sign up for another online course about behavioral psychology. But a nice bottle of wine at dinner? Suddenly I'm calculating the cost per sip and wondering what the server will think.

The stories we inherit about money

Where do these stories come from? For me, they're written in a thousand small moments from childhood. Watching my family clip coupons. Hearing "we have food at home" when passing McDonald's. Learning that wanting nice things was somehow morally inferior to making do with less.

These lessons served a purpose then. They were survival strategies, practical wisdom for stretching a paycheck. But at 44, still carrying them around like protective talismans, I have to wonder: what am I protecting myself from now?

There's this brilliant concept in psychology called "financial trauma," which isn't always about poverty or major loss. Sometimes it's about the subtle messages we absorb about our worthiness to have, to enjoy, to indulge.

The restaurant wine list becomes a test. Not of my wine knowledge or my bank balance, but of my internalized beliefs about what I deserve.

Breaking the pattern starts with awareness

So what changes when we recognize these patterns? Well, awareness is the first step, but it's not magic. I still feel that familiar discomfort when the wine list arrives. The difference is now I recognize it for what it is - old programming running in the background.

Last month, I experimented. At a restaurant I'd never return to, in a city I was just passing through, I ordered exactly what I wanted. Not the cheapest, not the second-cheapest, not the most expensive. I read the descriptions, asked the server for recommendations based on what I actually like, and made a choice based on preference rather than price positioning.

You know what happened? Absolutely nothing. The world didn't end. The server didn't judge me (or if they did, I'll never know). The wine was good. Maybe not transcendently better than my usual second-cheapest selection, but it was what I wanted, and that felt like a small revolution.

The permission we're really seeking

Here's what I'm learning: the permission we're seeking when we make these choices isn't really about money. It's about believing we're worthy of pleasure, of quality, of taking up space in the world without apology.

This extends far beyond restaurant wine. It's in the clothes we won't buy because they're "too nice for someone like me." It's in the opportunities we don't pursue because they feel above our station. It's in the compliments we deflect and the success we downplay.

The second-cheapest wine is safe because it requires no justification. It says, "I'm responsible but not cheap, discriminating but not pretentious." It's the choice that offends no one, including the harshest critic - ourselves.

But what if we stopped trying to thread this impossible needle? What if we acknowledged that sometimes we want the house wine because it's perfectly fine and we'd rather spend money elsewhere? And sometimes we want the nice bottle because we're celebrating, or it's Tuesday, or we just feel like it?

Wrapping up

I'm not advocating for reckless spending or lifestyle inflation. There's wisdom in living below your means and finding joy in simplicity. But there's a difference between conscious frugality and unconscious self-denial driven by shame.

The next time you're handed a wine list, or any menu of choices really, notice what happens in your body. Notice the calculations that aren't really about money. Notice the identity you're trying to project or protect.

Maybe you'll still order the second-cheapest wine. That's fine. But let it be a choice, not a compulsion. Let it be because you genuinely prefer it, not because you're performing a role you assigned yourself decades ago.

We get one life. The wine we drink, the experiences we choose, the space we take up - these aren't rehearsals for some future moment when we'll finally be worthy. We're worthy now, at 44, at whatever age you're reading this, worthy of choosing based on desire rather than shame.

Even if it takes us a few more restaurant visits to really believe it.