How to Date Without Going Broke

You think you’re just grabbing a couple of drinks. Next thing you know, you’ve spent half your rent on espresso martinis. Luke’s been there. His most expensive first date? $140 on drinks alone.

“We had like four espresso martinis each. I didn’t go to sleep five hours after.”

Dating is supposed to be fun, not financially terrifying. If you’re planning to go on dates regularly, especially in expensive cities, you need a strategy that protects your wallet and still feels effortless.

The Hidden Cost of Modern Dating

“Going on first dates like it’s really hard to budget. It’s so expensive.”

Luke’s right. Between dinners, drinks, and rides, dating can quietly burn through hundreds each month. And most of it isn’t about connection. It’s about pressure — the expectation to impress or compete.

But Luke figured out how to make dating sustainable without losing your social life or your savings.

“Find a spot with a deal cuz you will go broke.”

That’s Luke’s golden rule. He says, “I do a wine bar that I really like, it’s called BB Wine Bar 4th Street. They do $30 bottles from 5 to 8 p.m. every weekday. Absolutely fantastic if you’re somebody that’s gonna go on a lot of first dates like you want to just meet some people.”

That’s not cheap. That’s smart.

Here’s why it works:

• You know exactly what you’re spending

• It still feels like a real date

• The happy hour timing keeps things focused

• You can go again next week without stress

When you control the venue, you control the tone of the date.

Know Your Spot

Having one or two reliable go-to spots changes everything. You know the menu, the vibe, the staff. You’re comfortable, which makes the other person comfortable too.

It’s the same principle Josh talks about in The Confidence Routine That Rebuilds You — structure creates calm.

The Psychology of Smart Spending

When you’re not worried about the bill, you can be present. You’re not doing mental math halfway through the date. You’re actually listening.

That calm shows up in your confidence. It sets the right tone from the start. If someone needs a luxury dinner to have fun, that’s probably not your match.

For more on getting your money mindset right, read How to Build a Financial Life That Doesn’t Own You.

Luke’s Food Tour Hack

Luke says one of his favorite first dates cost almost nothing.

“We walked around the East Village. We got a 7th Street burger... We got one sandwich from each and then we went to Ray’s Candy Shop. Got some fried Oreos.”

It was low pressure, easy, and actually fun. That’s the point.

Walks, local food spots, or neighborhood hops work because they’re interactive. You’re building memories instead of just splitting the check.

Need inspiration? Check out The Best First Date Spots That Don’t Feel Like Interviews.

When Dates Get Expensive

Luke’s worst-case story still stings.

“The waiter came over and asked if we wanted another bottle of wine... I was going to respond no we’re okay thank you but they said yes we’ll take another bottle. And I’m paying. By the way, she knew that you were paying.”

It happens.

Here’s how to avoid it:

• Pick places with clear pricing

• Be upfront about the vibe before the date

• Suggest structured plans instead of open-ended nights

• If it goes sideways, pivot to a walk or coffee

Building a Sustainable Dating Budget

Dating should fit into your life, not wreck it. Two or three first dates a month can easily reach $200 or more. Over a year, that’s thousands.

Luke’s fix? Don’t stop dating. Just plan smarter.

Set a monthly dating budget. Find two or three go-to spots with solid deals. Keep track of what you actually spend. And stop equating cost with connection.

Need a starting point? Read The 20-Something’s Guide to Money That Actually Works.

The Bottom Line

Luke said it best. “

Find a spot with a deal cuz you will go broke.”

Dating doesn’t have to mean draining your account. The best experiences come from connection, not the price tag.

When you focus on what actually matters — conversation, comfort, and presence — you attract people who value substance over status.

The right person won’t care where you took them. They’ll care how you made them feel.

Want more real-world dating and money advice?
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