8 Things An Extravagant First Date Reveals And Why It’s A Huge Predictor Of A Relationship’s Failure

8 Things An Extravagant First Date Reveals And Why It’s A Huge Predictor Of A Relationship’s Failure

I went on a date once where the guy rented out an entire rooftop restaurant. Just for us. First date.

He ordered a bottle of wine that cost more than I am comfortable sharing and spent twenty minutes talking to the sommelier about the vintage. The food was incredible. The view was stunning. And I was miserable.

Because I didn’t know anything about him. I knew he had money. I knew he wanted me to be impressed. But I didn’t know what made him laugh, what he cared about, what he was actually like as a person.

The whole thing felt like a performance I was watching, not a conversation I was part of. And when he dropped me off, I felt emptier than if I’d just stayed home.

I dated him for two more months, and it was a disaster. The extravagance never stopped, and neither did the emotional distance. He could plan a perfect evening, but he couldn’t have a real conversation. He could spend money, but he couldn’t be vulnerable.

If you’ve been on an extravagant first date and something felt off, here’s what that over-the-top behavior actually reveals—and why it almost always predicts failure.

1. The Fancier The Date, The Less They Actually Say

A couple on an extravagant first date together.
Shutterstock

When someone leads with their wallet, it’s usually because they’re worried their actual self isn’t interesting enough. The fancy restaurant, the expensive wine, the elaborate plan—it’s all designed to keep you focused on the experience instead of the person providing it.

Research on dating behavior found something telling: people who prioritize expensive displays on first dates report lower comfort with emotional vulnerability and self-disclosure. Basically, the bigger the production, the smaller the person often feels inside.

And you can feel it. The conversation stays surface-level. They deflect personal questions. They talk about the menu, the wine, the view—anything except who they actually are. Because if the setting is impressive enough, they’re hoping you won’t notice there’s nothing substantial underneath.

2. Going Big On Date One Means They Skip The Important Steps

A first date should be low-stakes. Coffee. A walk. Something simple where you can just talk and see if you like each other.

But they skipped all that and went straight to the grand gesture.

And that reveals something important: they don’t understand how relationships work. They think you can buy connection. That if they spend enough money, skip enough steps, create enough wow factor, you’ll be hooked without them having to do the actual work of getting to know you.

But relationships aren’t built on that stuff. They’re built on small, repeated moments of actually showing up. And someone who doesn’t understand that is setting you both up for failure.

3. You’re Just A Part Of Their Image

Pay attention to where they take you. Is it a quiet place where you can actually talk? Or is it the hottest reservation in town, the place everyone wants to get into, the spot where they’ll definitely be seen?

Because sometimes the extravagant date isn’t about impressing you. It’s about impressing everyone else. You’re a prop in their performance of success. An accessory that completes the image they’re trying to project.

And you can tell. They spend more time looking around the room than at you. They name-drop. They make sure the right people see them. You’re not a person they’re interested in—you’re part of the aesthetic.

4. The Extravagant Start Is Designed To Hook You

Couple eating at a fancy restaurant on a first date.
Shutterstock

The intensity is the point. They’re overwhelming you with attention, affection, and expense so that you get swept up and ignore the fact that you barely know them.

It’s a strategy. Create such a high at the beginning that you’re hooked before you’ve had time to evaluate whether this person is actually good for you. And it works. You feel special. Chosen. Like you’ve found someone who really sees how valuable you are.

But love bombing always crashes. Because it’s not sustainable. And once they’ve secured your commitment, the extravagance drops off. Then, you’re left with a person who never actually built something real with you. Just an illusion that you’re now stuck trying to revive.

5. The Grand Gesture Is A Down Payment

When they treat you like royalty from the start, they’re banking on the fact that you’ll remember it later.

When they cancel plans. When they’re inconsiderate. When they show you who they really are and it’s not good.

You’ll think: but remember that amazing first date? They must really care. They’re just going through something. I should give them another chance.

And that’s exactly what they want.

The extravagance is an insurance policy.

A deposit of goodwill they can draw on when they inevitably mess up.

Because they know they’re going to. And they’re hoping the memory of the expensive dinner will keep you around long enough to forgive it.

6. They’ve Set A Bar They Can’t Actually Maintain

Couple having a date on a rooftop restaurant.
iStock

Here’s what happens after the rooftop restaurant and the expensive wine: real life. And real life is Tuesday nights on the couch. Splitting a pizza. Dealing with a bad day at work. Being tired and unsexy and completely ordinary.

But they’ve started at a 10. And now every date after has to compete with that first impression. Except it can’t. Because no one can sustain that level of extravagance indefinitely. So the second date is slightly less impressive. The third date is normal. And suddenly you’re wondering if they’re losing interest.

They’re not. They just can’t keep up the facade. But they’ve created this problem where anything less than extraordinary feels like a downgrade. And that’s exhausting for both of you.

Iwas confused when the rooftop-restaurant guy suggested we just order takeout and watch a movie for our fourth date. It was a completely normal suggestion, but after everything before it, it felt like rejection. Like I wasn’t worth the effort anymore. And that’s the trap. The extravagant start makes normal feel insufficient. And relationships are built on normal. On the boring, unglamorous, everyday moments of just being together. If normal feels like failure, the relationship is likely already doomed.

7. They Need You To Be Impressed More Than They Need To Know You

Pay attention to what they ask about.

Are they curious about your life? Your interests? What matters to you? Or are they more focused on whether you’re impressed by the wine, the view, the reservation they secured?

Because this whole thing isn’t about you. It’s about them. They need validation that they’re impressive. That they’re successful. That they can wow you. Your role is to be awed, not to be known.

I remember realizing halfway through that rooftop dinner that he hadn’t asked me a single real question. He’d talked about the restaurant, the wine, his job, his achievements. But he didn’t know anything about me. And he didn’t seem to care. He just needed me to be his audience.

8. They’re Trying To Hide Red Flags

They’re going big on the first date because they need you invested before you discover the problems.

Maybe they’re freshly separated and not actually divorced.

Maybe they have a temper they’re good at hiding for a few hours.

Maybe they’re emotionally unavailable, but great in the short-term.

Whatever it is, they know there’s something you won’t like once you get close enough to see it. So, they’re front-loading the wow factor. Creating such a spectacular first impression that by the time the red flags show up, you’ll be invested enough to overlook them.

And it works. Because when you finally see the problem—the anger, the avoidance, the ex who’s still very much in the picture—you’ll remember that incredible first date and think: but they’re capable of being amazing. I just need to get back to that version of them. Except that version was never real. It was just the bait.

Halle Kaye has been writing for Bolde since 2014. She writes primarily about dating, marriage, divorce, parenting, friendship and family dynamics.

As someone who is unapologetically hyper-independent, Halle writes extensively about people who are high-functioning, high-achieving and tend to rely exclusively on themselves. She writes about the origins of this psychological profile as well as the loneliness that often comes with it. She regularly shares her personal experiences navigating parenting, family and friendship with these tendencies and speaks candidly about those moments she wishes she had someone she could rely on.

Halle is also the author of the popular 2012 dating book Maybe He's Just an Ahole: Ditch Denial, Embrace Your Worth, and Find True Love! which was based on her dating experiences in college. Halle splits her time between Westport, CT and New York.