Back to Blog

How to Take Her on an Epic First Date Under Twenty Dollars Total

· 3 min read

Do you ever stress about what to do on a first date?

You do not want to be boring. You do not want to just go to a coffee shop and ask her a thousand questions like you are running an interview.

Learn this one first date sequence and never worry about a first date again.

  • The prop swap
  • The photo quest
  • The real conversation

One date. Three parts. Under twenty dollars total.

Have this go to in your pocket so anytime you need it, you do not have to think. You do not have to pre plan it. You know it is going to land. You know it is going to crush.

Will I seem cheap?

Unless she is a gold digger, there is no chance she walks away thinking you are cheap. She will respect you for giving her a unique first date she will actually remember.

If you execute this and it does not crush, forget about that girl. She is not cool. Move on.

Part 1: The prop swap

Couple wearing fake mustaches and silly hats on a first date

Each of you gets ten dollars. Hit a vintage or thrift store. You buy a prop for her. She buys a prop for you. No veto. Whatever they pick, you wear or carry for the rest of the date.

Great contenders: fake mustaches, fake hair pieces, superhero costumes, silly hats. Anything ridiculous works.

Alternatively, bring your own props if you already have some. Bring several, split them into two groups, and tell her she has to pick what you wear but she has to wear the rest of it.

Part 2: The photo quest

Before the date, pick two landmarks around your town. A mural, a statue, a weird sign, whatever is nearby and free.

At each stop, take a silly photo. Props stay on in every shot. Get strangers to take at least two of the pictures. Walk between stops and make it feel like a scavenger hunt.

Get creative. Here are some silly photo ideas for inspiration:

Silly couple photo idea Silly couple photo idea Silly couple photo idea Silly couple photo idea Silly couple photo idea Silly couple photo idea Silly couple photo idea Silly couple photo idea Silly couple photo idea

Part 3: Real conversation

End somewhere calm. A park bench, the waterfront, a quiet café window. Take turns asking real questions.

Write these down on your phone and bring them to the date:

  1. What are you most trying to change about your life?
  2. What title would you give this chapter in your life?
  3. If you could get to know someone in your life on a deeper level, who would it be and why?
  4. What is the most unexplainable thing that happened to you?

Games like We're Not Really Strangers have plenty more if you want them.

Fun, silliness, and real conversation. Everything you need for both of you to figure out if you want to keep spending time together.

Find someone worth taking on this date

Pretty Good Dating is about finding real connections. We help you match with people who want the same thing, have fun getting to know each other, get along, and pair off with someone who could be your person.

Join the waitlist when you are ready.

Ready to find your person?

Join the waitlist for Montreal's newest dating site. No swiping, no algorithms.

Join the Waitlist