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Post(perfect)mates Delivery Date

INDOOR / OUTDOOR · COST: $$$ · FOOD: YES · DRINKS: NO

This might sound crazy at first, but hear me out...
You and your date hop in your car with the Fleet App open, ready to pick-up food for lazy lunch-wanters. Pop on some music (Spin Doctors - Two Princes, is never a bad choice), and head out to pick up your first order.

On route, you and your date have so many built-in things to talk about (the music, the restaurant choices of the people ordering, why the person was too busy to pick up their own food, etc.)
I think it's funny to play "Dr. Delivery Driver" and do pseudo-analysis of the customer based on the tiny bit of information you have to go on. Make it fun, make it funny.

You can go one step further and have your date order thru Postmates so you can pick it up/deliver it to them!

The Overview

WHAT You Need
Earn $$$ while going on dates!

No joke, it doesn't get any cheaper than negative costs! This idea is genius for like 6 different reasons!

Load up your Fleet App (or Instacart or Grubhub or whatever delivery driver app you use), get in your car with your date, and wait for orders.
Again, you'll need to do this during a peak time for best results... otherwise you'll just be sitting in your car with someone you might not really know very well yet.
Another good tip is to be somewhat close to a number of popular restaurants. Some prior scouting can do a world of good for this (as in: do a test run alone to see which restaurants are most popular and during what times so you know where to hedge your bets toward).
All in all, if you play your cards right, you can have a fun time earning some extra cash and possibly even end up with a really cool date story.

WHEN to do it
Breakfast, Lunch, and Dinner!

This should be a no-brainer. While your standard "romantic encounter" usually happen within a certain section of the clock, this date lends itself to an "outside of the box" experience.

While many dates tend to be an evening thing, you could have some real fun hanging with your newest hot-homie and delivering lunch to people too lazy to go pick it up themselves!

For that reason, an afternoon delivery date during a mid-week lunch rush is a great construct for a memorable time.

WHERE to go
No Planes or Trains, but yes @ Automobiles

So, this wouldn't be 100% accurate if it didn't include the option of a tandem-delivery-bicycle. Yes, that is a possibility. Plausible? Not exactly.

But more than likely, you'll be in a car (either yours or your date's). The car can be great because you essentially have a captive audience (and not captive in the way a crazy person would mean it) who you can get to know without the standard distractions of a bar, restaurant, or whatever dive your date destination would have been.