The $100,000 Question

As a father watching my daughter prepare for an engagement to a young man I admire deeply, I find myself wrestling with a dilemma I never anticipated: Should a young couple spend $100,000 on a dream wedding or use it as a down payment on their first home? 

For my daughter, the vision of her wedding day is something she’s cherished for as long as I can remember. She’s often talked about the flowers, the gown, and the perfect setting. Her Pinterest vision boards are full of it. She’s seen friends planning their weddings and the joy of making that dream a reality. To her, the wedding isn’t just a celebration; it’s the culmination of years of imagining a day that’s all about love, family, and starting this new chapter in the most magical way possible.

At the same time, the realities of finances and the soaring cost of homeownership in San Diego have entered the conversation. The question of where to prioritize resources has become a poignant and very personal discussion. It’s a beautiful aspiration, but one colliding with the harsh realities of finances and priorities—especially in coastal San Diego, where housing costs are staggering and wedding budgets often balloon beyond reason. 

As a very proud father, I welcome you to dive into the heart of this dilemma with me by exploring the emotions, aspirations, and practical realities shaping their decision.

The Wedding: A Day to Remember 

My daughter recently shared her excitement about planning her wedding someday. One of her best friends is currently engaged and navigating the whirlwind of venues, vendors, and budgets, so she has a front-row seat to the joy—and stress—of wedding planning. For her, a wedding is a moment to shine, surrounded by love, family, and friends.

The Emotional Argument 

- A Lifelong Dream Realized: Like many young women, my daughter has spent years imagining her wedding day. The idea of walking down the aisle, surrounded by loved ones, feels like the perfect start to her marriage.

- A Shared Celebration: Weddings aren’t just about the couple; they’re about family and community. It’s a chance to gather loved ones and celebrate a bond that feels rare and precious. 

- A Lifelong Dream: Like many young women, she’s imagined this day since she was a child. It’s her chance to turn those Pinterest vision boards into reality. 

The Financial Reality 

I used $100,000 as an example, but I know weddings can be done for less. Still, even the most frugal couples often find costs swelling—guest lists grow, dream venues charge a premium, and “just this once” splurges add up quickly. 

But no matter how unforgettable the day may be, a wedding is an expense, not an investment. Once the last song plays and the lights dim, what’s left is only memories—and, potentially, a hefty financial hangover. 

The First Home: A Stepping Stone to the Future

When my daughter and her boyfriend shared that they ran the numbers on buying a home, I could tell they were a bit discouraged. They’d taken my suggestion to heart and used rent vs. buy calculators to compare the cost of owning a modest condo versus continuing to rent. Their conclusion was that buying wasn’t going to get them the home they really wanted—not yet.

I get it. I’ve been there. When I bought my first home, it wasn’t a dream property. It was a small condo in a not-so-glamorous neighborhood. But it was ours. It represented a step forward. And that’s what I tried to share with my daughter: Your first home doesn’t have to be your forever home. It’s a stepping stone—a way to start building equity and moving closer to that dream.

University City: A Realistic First Step

In University City, a two-bedroom, one-bath condo is currently listed for $620,000. It’s nothing flashy, but it’s a solid entry point into San Diego’s real estate market. Considering today’s rates and putting 10% down, they’d be looking at a mortgage of approximately $4,600/mo. Now, compare that to renting a similar unit, which costs around $3,400 per month. The calculators tell us that if you stay in the condo for longer than 5 years and 6 months, buying becomes cheaper than renting. That doesn’t sound awesome!

But here’s the thing: Those calculators only scratch the surface.

For my daughter and her boyfriend, a place like that University City condo could serve as their first step. No, it’s not the big family home they dream of, but it’s a foot in the door of San Diego’s competitive real estate market. It’s a way to start building equity and working toward something bigger.

The Bigger Picture

When you buy, you’re not just solving for today’s living expenses—you’re setting yourself up for tomorrow. Every mortgage payment chips away at your loan balance, building equity. As your property appreciates—and in San Diego, homes typically gain 8–12% in value annually—you’re creating wealth.

Renting, on the other hand, is like running on a treadmill. It may feel comfortable, but you’re not really going anywhere. Sure, it might seem easier to save while renting, but with San Diego’s rising home prices, saving alone likely won’t keep pace with the market.

As a comparison, assuming an 8% appreciation year-over-year on our $620,000 new condo, in order to save on par with appreciation, they will need to squirrel away $50,000 a year to maintain pace with appreciation. This doesn’t take into account the amount they will pay down their mortgage in one year, nor the tax benefits of owning their home come tax time.

The Cost of Waiting

When they told me they’d decided to keep renting for now, I challenged them. “How are you going to save your way to financial freedom?” I asked. The truth is, most people can’t—not when rent consumes such a significant portion of their income. Meanwhile, as they wait, property values continue to climb, making it even harder to catch up.

I told them, “Your first home doesn’t have to be perfect. It just has to be yours.”

Owning a home changes your trajectory. Once you’re on the property ladder, you’re in the game. You’re building something that grows with you instead of paying into someone else’s investment.

Final Thoughts

The calculators say buying takes 5.5 years to beat renting financially. That’s helpful information, but it misses the bigger point: Owning a home is a long-term investment. It’s not about where you start; it’s about where you’re going.

For my daughter and her boyfriend, this decision isn’t easy. It wasn’t easy for me, either, when I was starting out. But I know from experience that those early sacrifices—choosing something modest, sticking with it—pay off in ways they can’t yet imagine.

If they decide to take that step, I’ll be there to help paint the walls, hang the shelves, and remind them that this is just the beginning of their story.

Balancing Aspirations: The $100,000 Question 

It’s clear this isn’t just about money—it’s about values, priorities, and dreams. Here’s where I think compromise can come into play: 

- A Modest Wedding: Scaling back the wedding doesn’t mean sacrificing its magic. Intimate weddings with personal touches can be just as memorable. 

- A Practical Home: Starting small doesn’t mean starting wrong. A condo or townhouse in a good location can be a strategic first step. 

- Blended Support: As parents, we can offer guidance and financial support that helps them achieve both goals. Perhaps splitting the funds—half for the wedding, half for the down payment—is a way to honor both dreams. 

A Personal Reflection 

I think back to the first home my wife and I bought. It wasn’t glamorous, but it was ours. We painted the walls together, argued over furniture placement, and laughed about the clunky dishwasher that rattled like a freight train. Those memories weren’t tied to perfection—they were tied to progress, to building something together. 

For my daughter, I hope for the same: a place where love, laughter, and imperfections create something far more valuable than granite countertops or vaulted ceilings. 

I also understand her desire for a wedding that symbolizes love, unity, and joy. As her dad, I want her to have it all—but I also want her to understand the bigger picture. A wedding is a beautiful start, but a home is a lasting foundation. 

A Father’s Challenge 

As we continue these conversations, I’ve challenged her and her boyfriend to reconsider their assumptions. Renting may feel like the easier choice, but I know that saving their way to financial freedom will be an uphill battle in San Diego’s market. Homeownership might feel out of reach now, but with thoughtful planning—and perhaps a touch of parental support—they can set themselves on a path toward stability and growth. 

To my daughter, I say this: Love is the thread that ties it all together. Whether you prioritize the wedding, the home, or both, remember that the decisions you make now will shape the life you build together. And as your dad, I’ll be there every step of the way, cheering you on, offering advice, and maybe sneaking in a few subtle nudges toward the practical side. 

Love, Dad