More than the money, Preston had just revealed something crucial. He saw our family as beneath his. We were the charity case he was graciously allowing into his circle, as long as we paid the admission fee.
«I need some time to think about this,» I said.
«Of course,» Preston said quickly. «But like I mentioned, we really need an answer by Friday. The Chandler won’t hold the date much longer.»
Three days. He was giving me three days to come up with money he assumed I didn’t have.
After I left their apartment, I sat in my Honda for a long time, thinking. Anna was miserable, choosing between her family’s financial security and her future happiness, all because Preston was too proud to have a wedding that didn’t impress his country club friends. But here’s what Preston didn’t understand: I’d spent 25 years in banking.
I had learned to recognize certain patterns: entitlement, arrogance, and the assumption that money equals worth. I’d also learned that information is power. That night, I called my compliance department, which was not unusual for a bank president requesting account reviews.
By Thursday morning, I had a complete picture of the Whitfield family’s financial situation. It included Preston’s trust fund, his father’s business ventures, and most interestingly, the mortgage on their family estate. The beautiful eight-bedroom colonial in Newport—the one Preston had grown up in, the one his parents used for entertaining senators and mayors—was mortgaged through Romano Financial for $4.2 million. According to our compliance review, there were some very interesting character clauses in that mortgage agreement.
Friday afternoon came, and Preston called exactly at 5 o’clock. I was in my office at Romano Financial headquarters, having just finished reviewing the Whitfield mortgage file with my legal team.
«Mr. Romano, I hope you’ve had time to consider our conversation.»
«I have.»
«Great. So what’s the decision on the venue contribution?»
I leaned back in my chair—the chair in the office Preston thought belonged to someone else entirely. «Preston, I have a question for you first.»
«Of course.»
«You mentioned that this wedding represents both our families. I’m curious what you think my family brings to this… partnership.»
There was a pause. «Well, Anna, obviously. She’s wonderful. Smart. Beautiful.»
«Beyond Anna. What do you think the Romano family contributes?»
Another pause, longer this time. «I’m not sure I understand the question.»
«You’ve made it clear that your family has connections, social standing, and financial resources. What do you think we offer in return?»
I could practically hear him searching for a diplomatic answer. «Every family has their own unique strengths.»
«Unique strengths such as?»
«Mr. Romano, I’m not sure where this is going.»
«I’m trying to understand why you think $50,000 is a reasonable request from a family you clearly consider financially inferior.»
The silence stretched. When he spoke again, his voice had an edge. «I never said you were financially inferior.»
«You said I probably make $60,000 a year.»
«That was an estimate based on average bank employee salaries.»
«Which bank?»
«What?»
«Which bank did you research for those salary estimates?»
«I… it was a general…»
«You assumed, Preston. You saw my car, my clothes, my neighborhood, and you made assumptions about what kind of man your fiancée’s father is.»
His breathing changed; I could hear him getting defensive. «Mr. Romano, if you’re upset about the financial arrangement, we can discuss alternatives.»
«Such as?»
«Well, if $50,000 is too much, perhaps we could look at a smaller venue. Something more suited to everyone’s budget.»
More suited to everyone’s budget. The translation was clear: cheaper, more appropriate for people like us.
«Or,» I said, «we could look at this from a different angle.»
«What do you mean?»
«Tell me about your family’s finances, Preston.»
«Excuse me?»
«You’ve analyzed mine. Sixty thousand dollars a year, you said. Community bank employee. Limited resources. Turnabout seems fair.»
«That’s… that’s completely inappropriate.»
«Is it? You’re asking me to contribute $50,000 to an event that benefits your social standing. Shouldn’t I know whether your family can actually afford their portion?»
His voice rose. «My family has been in Newport for four generations.»
«That’s not what I asked.»
«We own property.»
«Mortgaged property?»
Dead silence. «Preston, how did you… What are you implying?»
I kept my voice level. «I’m not implying anything. I’m asking direct questions about financial capacity, the same way you’ve been assessing mine.»
«This is ridiculous. My family’s financial situation is none of your business.»
«But mine is yours?»
«That’s different. You’re being asked to contribute.»
«And your family isn’t contributing?»
«Of course we are.»
«But how much? Fifty thousand? A hundred? More?»
I could hear him breathing hard. «Mr. Romano, I don’t appreciate this line of questioning, and I don’t appreciate being treated like a charity case by someone who doesn’t know the first thing about my actual situation.»
«Your actual situation? You drive a 20-year-old Honda and live in Federal Hill.»
«And what does that tell you about my priorities?»
«It tells me you don’t have money to waste on expensive cars and fancy neighborhoods.»
«Or,» I said quietly, «it tells you that I don’t need expensive cars and fancy neighborhoods to feel good about myself.»
Another long silence.
«Look,» Preston said, his tone shifting to something meant to be conciliatory. «Maybe we got off on the wrong foot here. The truth is, Anna is marrying into a family with certain expectations, social obligations.» He continued, «If your family can’t meet those expectations financially, that’s understandable. But we need to be realistic about what that means for the wedding and, frankly, for Anna’s future social position.»
There it was, the real message. Anna was marrying up, and our family needed to pay admission to the upper class or accept a lower status permanently.
«So if I can’t pay the $50,000, then we’ll have to make adjustments? Find something more appropriate for the ‘combined financial reality’?»
«Anna will adjust. She’s smart enough to understand that marriage involves compromise.»
Anna will adjust. As if she should be grateful for whatever scraps of dignity Preston was willing to throw her way.
«I see,» I said. «Preston, let me ask you one more question.»
«What?»
«Do you love my daughter?»
«Of course I do.»
«Enough to marry her if her family had no money at all?»
The pause that followed told me everything I needed to know.
«Mr. Romano, that’s a hypothetical.»
«No, Preston. It’s the only question that matters.»
I hung up and looked at the Whitfield mortgage file on my desk. Four-point-two million dollars. Character clauses clearly defined. Legal grounds well established. It was time for Preston to learn what financial reality actually looked like.
That weekend, Anna invited me to lunch at a small cafe near Harvard Square. She looked exhausted, with dark circles under her eyes that reminded me of her mother during her hardest days at law school.
«Dad, about the wedding thing with Preston…»
«Anna, you don’t need to explain anything.»
«But I do.» She stirred her coffee without drinking it. «He’s not usually like this. The pressure from his family is intense. They have these expectations about status and appearances that I’m still learning to navigate.»
Learning to navigate. Like she was the one who needed to change.
«What kind of expectations?»
«Well, for example, his mother asked me last week what my father does for work. When I said banking, she asked which firm. When I said community banking, she got this look.» Anna trailed off.
«What kind of look?»
«Like she was disappointed but trying not to show it. And Preston’s father keeps making these comments about self-made people and how much he respects families who’ve worked their way up. But the way he says it, it sounds like… like he’s patting us on the head for trying so hard.»
«How does that make you feel?»
«Honestly? Sometimes I wonder if I belong in that world at all. Last month, Preston took me to a dinner party at his parents’ house. Everyone was talking about their vacation homes, their children’s private schools, and their charity galas.»
«When someone asked what I did,» she continued, «I said I was finishing my MBA at Stanford. This woman, I think she was a judge’s wife, said, ‘How wonderful that you’re getting an education. That must be such a priority for families like yours.'»
Families like yours. The condescension was unmistakable.
«What did you say?»
«Nothing. I just smiled and changed the subject. But later, Preston said I’d handled it well, like I’d passed some kind of test.»
My phone buzzed. It was a text from Maria, my sister and Romano Financial’s VP of Operations. «Compliance completed the Whitfield review. Character violations documented. Emergency board meeting scheduled for Monday. You want me to prepare the foreclosure paperwork?»
I typed back, «Yes. And prepare the trust fund freeze documentation as well.»
Anna noticed me checking my phone. «Sorry, Dad. Work emergency?»
«Something like that.» I put the phone away. «Anna, can I ask you something?»
«Of course.»
«Are you happy?»
She was quiet for a long moment. «I love Preston, I do. But sometimes I feel like I’m auditioning for a role in his life instead of just living my life.»
«What would happen if you stopped auditioning?»
«What do you mean?»
«What if you just showed up as yourself? As Anna Romano from Federal Hill, whose father works at a bank and drives an old Honda? What if you stopped trying to translate yourself into something they’d find acceptable?»
She looked down at her hands. «I don’t know if Preston would still want to marry me.»
The honesty in that statement broke my heart and solidified my resolve. My phone rang. The caller ID showed Romano Financial’s legal department.
«I should take this,» I said to Anna. «Give me one second.» I answered, «This is Tony.»
«Mr. Romano, this is David from legal. We’ve completed the documentation you requested. The Whitfield mortgage contains clear character violation clauses. We have grounds for immediate acceleration. Do you want us to proceed?»
«Schedule it for first thing Monday morning, full legal review.»
«Should we notify the account holders?»
I looked at Anna, still staring at her coffee, still wondering if she was good enough for people who should be grateful she even looked in their direction. «Not yet. I’ll handle notifications personally.»
I hung up and turned back to Anna. «Sorry about that.»
«No problem. Banking emergencies, right?»
If only she knew what kind of banking emergency this was going to be.
«Anna,» I said, «I want you to remember something. You never have to apologize for who you are or where you come from. Anyone who can’t see your worth doesn’t deserve you.»
She smiled sadly. «Thanks, Dad. I just wish it was that simple.»
It was about to be.
The Yacht Club invitation arrived on elegant cream cardstock: The Whitfield family cordially invites you to celebrate the engagement of Preston Whitfield IV and Anna Romano. Cocktails and dinner at the Newport Country Club, Saturday, April 20th, 7:30 in the evening. Jacket required.
Anna called me that Tuesday, excited and nervous. «Dad, Preston’s parents want to meet you properly. His mother said it’s important for the families to get acquainted before we start serious wedding planning.»
Before we start serious wedding planning. Translation: before they decide whether we’re acceptable.
«I’ll be there,» I said.
«Great. And Dad, maybe wear your navy suit? The one from my graduation?» Even she was worried about appearances.
