The Real Cost of Dating: How to Date Without Going Broke

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

Luke learned this lesson the hard way during his early dating days in NYC. His cautionary tale? Spending $140 on espresso martinis on a single first date. "We had like four espresso martinis each. I didn't go to sleep five hours after."

If you're planning to date regularly - especially in expensive cities - you need a financial strategy that doesn't compromise your ability to make genuine connections.

The Hidden Cost of Modern Dating

The Expensive Reality

Luke's experience illustrates how quickly dating costs can spiral:

• $140 for one date on espresso martinis alone

• Multiple dates per week when you're actively meeting people

• Dinner, drinks, activities adding up to hundreds monthly

• Transportation costs (Ubers, parking, etc.)

When someone in the last Guyset episode asked about budgeting, Luke's response was telling: "Going on first dates like it's really hard to budget. It's so expensive."

The Pressure to Spend

There's an unspoken expectation that good dates require expensive venues. This creates pressure to:

• Choose upscale restaurants to make good impressions

• Order multiple rounds of drinks to extend conversations

• Suggest activities that cost significant money

• Compete with other potential dates who might spend more

But Luke's approach proves you can create memorable experiences without breaking the bank.

Luke's Smart Dating Strategy

Find Your Go-To Spot with Deals

"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."

This strategy works because:

• Predictable costs - you know exactly what you'll spend

• Quality experience - still feels like a proper date

• Timing incentive - the happy hour timing keeps dates shorter and more focused

• Repeatable - you can use the same spot multiple times without feeling cheap

Know Your Venue

Having a regular spot provides several advantages:

• Familiarity with the menu and pricing

• Comfortable atmosphere where you can focus on conversation

• Staff recognition which can enhance the experience

• Backup plan that doesn't require research for each date

The Psychology of Budget-Friendly Dating

Removing Financial Stress

When you're not worried about the bill, you can:

• Focus entirely on getting to know the other person

• Stay present in conversations instead of calculating costs

• Make decisions based on genuine interest rather than financial commitment

• Avoid the awkwardness of unexpectedly expensive situations

Setting Appropriate Expectations

Luke's $30 bottle approach sets a reasonable spending precedent that:

• Shows you're willing to invest in a nice experience

• Doesn't create pressure for elaborate future dates

• Filters for people who appreciate thoughtful choices over expensive gestures

• Demonstrates financial awareness rather than reckless spending

Alternative Budget-Friendly Date Ideas

Luke's Food Tour Success

His most memorable first date wasn't expensive drinks - it was a curated food tour: "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."

This approach cost significantly less than a fancy dinner while creating a more memorable and interactive experience.

The Activity-Based Strategy

Instead of expensive sit-down dates:

• Walking tours of neighborhoods you know well

• Food sampling at different affordable spots

• Free outdoor activities with optional food/drink stops

• Happy hour specials at quality establishments

When Dates Get Expensive (And How to Handle It)

The Wine Ordering Incident

Luke shared a horror story about a date who ordered additional expensive items without consulting him: "The waiter came over and asked if we wanted another [bottle of wine] to which I was going to respond no we're okay thank you but like... they decided to say yes we'll take another bottle... And I'm paying. By the way, she knew that you were paying."

How to prevent this:

• Set expectations early about the type of venue and spending level

• Be clear about budget constraints without being awkward about it

• Suggest specific activities rather than open-ended "let's see what happens"

• Have polite exit strategies for dates that are spiraling financially

The Expensive Mistake Recovery

When Luke found himself in an unexpectedly expensive situation, his strategy was: "At this point I'm like just slamming cups of wine trying to like finish this bottle very quickly."

Better approaches:

• Politely suggest splitting if costs are getting out of hand

• Transition to a different venue ("Should we get some air and walk around?")

• Be honest about budget ("I'm trying to be mindful of spending this month")

• Learn from the experience to avoid similar situations

Building a Sustainable Dating Budget

The Monthly Reality Check

If you're going on 2-3 first dates per month plus follow-up dates with people you like, costs can easily reach:

• $50-100 per first date (conservative estimate)

• $150-300 monthly just for first dates

• Additional costs for second dates, third dates, etc.

• $2000-4000 annually on dating expenses

Smart Budgeting Strategies

Set Monthly Limits:

• Decide how much you can realistically spend on dating

• Track expenses to understand your actual spending patterns

• Include dating costs in your overall entertainment budget

Find Your Regular Spots:

• Identify 2-3 venues with good deals for different types of dates

• Build relationships with staff for better service

• Know the menus and pricing to avoid surprises

Plan Ahead:

• Research affordable options in advance

• Have backup plans for different budgets

• Consider timing (happy hours, lunch dates, etc.)

The Long-Term Perspective

Quality Over Quantity

Luke's approach recognizes that meaningful connections don't require expensive venues. The food tour date he raved about cost significantly less than fancy restaurant meals but created a more memorable experience.

Sustainable Dating Habits

When you develop sustainable spending habits for dating:

• You can date more consistently without financial stress

• You attract people who appreciate thoughtfulness over extravagance

• You build skills in planning creative, engaging experiences

• You avoid the boom-bust cycle of expensive dates followed by dating breaks

Red Flags About Money and Dating

Warning Signs to Watch For

Based on Luke's experiences, be cautious of:

• People who order expensive items without discussing it

• Expectations of elaborate first dates before you've even met

• Lack of consideration for who's paying

• Pressure to spend more than you're comfortable with

Green Flags

Look for people who:

• Appreciate creative, budget-friendly suggestions

• Offer to split or contribute to date costs

• Focus on conversation and connection over venue prestige

• Suggest alternative activities when costs are a concern

Your Dating Budget Action Plan

This Month:

1. Calculate your actual dating expenses from the past few months

2. Set a realistic monthly dating budget you can sustain long-term

3. Research 2-3 regular spots with good deals in your area

4. Plan some creative, low-cost date ideas you're excited about

Ongoing Strategy:

1. Track spending to stay within your budget

2. Build relationships with staff at your regular spots

3. Develop confidence in suggesting budget-friendly alternatives

4. Focus on experiences that showcase your personality rather than your wallet

The Bottom Line

Luke's dating budget wisdom comes from real experience: "Find a spot with a deal cuz you will go broke."

Dating doesn't have to be expensive to be meaningful. In fact, some of the best connections happen when you're focused on getting to know each other rather than impressing with expensive venues.

The goal is to create sustainable habits that let you date consistently without financial stress. When you remove money anxiety from dating, you can focus on what actually matters: building genuine connections with people who appreciate you for who you are, not how much you spend.

Remember, the right person will be impressed by your thoughtfulness and creativity, not your credit card limit. And if someone judges you for suggesting a wine bar with $30 bottles instead of $200 dinners, they're probably not the right person for you anyway.

Want more practical advice for dating on a budget and managing your finances in your twenties? Subscribe to Guyset for weekly insights on dating, money, and building a sustainable adult life.