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Coffee, Lotto, a Walk & a Convo


This is a great date to learn about the person you like—and a good way for them to learn about you!

This premise of this date gets you talking about something you both enjoy—your dreams & fantasies. I emphasize there are no wrong answers & nothing is off limits, but most of the time stuff just centers around people quitting their jobs in glorious “Half Baked” fashion; telling their boss to shove it and F’ everyone else.

If the coffee place is near the waterfront or something interesting, you can go for a walk with your date & talk about the property you’ll buy once you’re rich. Often, there are fancy houses lining the waterfront and you can guesstimate the value… then get on Zillow and find out the actual number!

If the waterfront isn’t an option & your date trusts you enough to ride in your car, you can go drive to a fancy neighborhood, park your car somewhere inconspicuous (especially if it’s shitty—it’ll stick out among all the BMWs and Benzes) and then take a stroll through the neighborhood, waving to your future neighbors… or at least planning how you’d rob each perspective house.

  • Where would you live: Stay put where you are and live a humble life? Or buy an extravagant palace for all your new pet tigers?
  • What would you do for fun/entertainment: Granted, the size of this jackpot may determine if you’re going to help feed the hungry or start the Hunger Games—what will you do for fun with your winnings?
  • Cars, Yachts, Mansions, etc—where’s your money go: What do you think your primary expenses will be? Faberge egg habit? Lavish multi course meals every night? Personal chauffeur to show you around? What crazy thing are you making a priority now that you’re rich?
  • Who is going to be asking you for money? Family? Friends? Basically, if we get together, who do I need to worry about trying to weasel in on our hard earned fortune?

The Overview

WHAT You Need

Coffee, Lotto ticket, and a place to walk

Coffee can always be subbed for something else, but it's not the greatest idea to try and get tipsy and then go walk a bunch (granted, this is good practice for getting pulled over I guess?)

WHEN to do it

Anytime's good for Coffee!.. and walks... except night.. or heavy rain..

You should probably pick this one strategically, unless you work like graveyard shift or are some kind of insomniac.
Regardless, you can probably figure out a good When based on your caffeine tolerance.

WHERE to go

Coffee shops are everywhere, throw a damn dart

Pick whichever place you think is good, but the idea is that it should be near a good place to take a walk.
The aim is to not have to hop in the car and drive to a place to then go walk.