Dates for PEOPLE WATCHING



Fabulous ($5) Shopping Spree

WHAT

$5 (plus tax) and a sense of humor

A good sense of humor is probably the most important aspect of this date. Once your companion realizes you're headed to the Dollar Store, there might be some initial resistance. For that reason, it's generally best to keep it cryptic about the destination address.
But fret naught, it's easy to overcome and I explain exactly how I conduct this outing.
Obviously, without a Dollar Store... this date pretty much doesn't work.
And of course, without your $5+, you'd otherwise be leaving empty handed.
Take your date by the hand, and walk each isle, suggesting items for one of their 5 and asking their opinion on each thing that catches your eye. At the end, ring up your purchase and go find something fun to do with the 5 items.

WHEN

When do they close?

I almost made this mistake once and had to rush to make it with my date before they closed. So, lesson learned is check the store hours during the planning phase of this outing. 9pm was when the Dollar Stores closed for me, but Dollar Tree or Dollar Emporium or Dollar-Whatever you have in your area probably have different hours.

WHERE

Dollar Store Locations

Better make sure there are at least a couple options in your area and you're not having to drive 45 miles each way to spend $5.

READ MORE..




Zombie ACOSTCOlypse

WHAT

Costco Membership (or just goto Wal-Mart) and some Zombie knowledge

If you've never seen a a zombie movie before, you're going to need to be a fast learner.
Also, you'll probably need to grab a shopping cart (duh...) and maybe even a disguise (assuming you want to come back here and shop someday).

WHEN

Special Holiday Hours? Or is it just Tuesday?

Pretty straight forward way to narrow down the "when" is: business hours.
Short of being a key-holding store employee, you will probably need to stick to the standard open-to-close times provided on their website.
But once you have that window figured out, you can further determine the best time. Weekend afternoons are AWAYS going to be busy, but they are also always going to have the 'Senior Buffet' aka the billion sample brunch. There will be no less than a dozen employees, setup & handing out food samples. While you're filling your cart with survival essentials, make sure to fuel-up with all the samples you can eat. Plus, this may possibly save you from having to pay for a real meal later. Always thinking...

WHERE

Costco Locations

Better make sure there are at least a couple options in your area and you're not having to drive hours to find a warehouse club store

READ MORE..




I Think I L-IKEA You

WHAT

Browse IKEA displays & role-play your future

What would your lives be like living in this display room? Does IKEA rent these rooms out after-hours to people? Maybe a new revenue stream for them...? Like an AirBnB, but IKEAirBnB. They can even provide a continent breakfast (only 1 continent). I don't know, but it's something you two can discuss..

WHEN

Timing is important.. but so are Business Hours

Play it safe, go check their website and figure out when they close. Yes, I too like to live dangerously, but some things you just don't leave to chance...

To further drill down, what are you looking for? Relaxed conversation? A platform for people watching? If it's busy (like on the weekends or around "back to school" time), you will have a slew of interesting people to observe and create backstories for. Otherwise, if you want a little less chaos, you might want to stick to non-peak hours/days.)

WHERE

IKEA Locations

Hopefully there's an IKEA location around you (you can use the "Find A.." feature to check). Assuming so, then this should be pretty straightforward.
If there is NOT an IKEA location close by to you... pick a different activity.

READ MORE..




Self-Help Section Projection

WHAT

Walking around the bookstore, making up bullshit

Start out in an easy section like weird diseases or the area dedicated to Psychological and Sociological Disorders and branch your way out to rows the require more imagination.

WHEN

Bookstores have hours... and criminals have lockpicks?

Probably safest to just stick to regular business hours. Pick a time when they're open and not super busy, then get in and do your thing!

WHERE

Large Bookstores like Barnes & Noble or others

The bigger and more bustling, the better. The larger an area to wander around, the more time you can spend and the more ideas you can get to talk about.

READ MORE..




Coffee, Lotto, a Walk & a Convo

WHAT

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

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

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.

READ MORE..




Trail Mix & an Urban Hike

WHAT

"Hikes need trail mix..."

Everybody loves a hike. Well, some people like them. However, there's not always a great place to GO for a hike; maybe you live in the city?
Not to fear! You can even kick it up a notch by adding in a DIY-trailmix portion to the date!

Hit the best bulk-food section of your local grocery store and create a trailmix concoction you and your date can munch on while you wander.

WHEN

Day, Night, Sun, Rain, Snow... eh, mostly just Sun..

Any time is fine, as long as you are ok with the elements. Sunny afternoons work great, but sometimes a stroll around sunset or an early morning excursion will better fit the bill. An umbrella and boots may be necessary if you live in the Pacific Northwest (but if you're really from here, you don't use an umbrella). Consider you'll be outside, it could be slippy (this is apparently a Pittsburgh) so make sure your footwear is appropriate. If it's after sunset, consider bringing a flash light (and then you can tell ghost stories or something later when you find a park bench).

WHERE

A city stroll or high-rise hopping

Pick a walk around your city--
Include stair-cases, hills, even buildings with elevators! You can use something like MapMyRun to create a route and utilize your phone's GPS to keep on track.
Something fun

READ MORE..




Post(perfect)mates Delivery Date

WHAT

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

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

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.

READ MORE..




Thrift Store Scavenger Hunt

WHAT

"I'm like basically an Indian Guide.. what are we looking for again?"

Find a decent thrift store, a good day to go, and someone to join the journey.
You can create your own list of things to find, or you can use some of the items in here.

Here are some things to find:

  • The fanciest item
  • The best Summer outfit
  • The best secret disguise
  • The worst shirt/top
  • A uniform of some type
  • A green sweater
  • The worst picture frame for a sexy photo

WHEN

Basically during store-hours... unless you're good at picking locks.

If so, you can pretty much go whenever you want then.
(best to have a decent escape plan or a getaway ride waiting if you are choosing to B&E)

WHERE

Thriftstores and Second Hand shops

Goodwill, Salvation Army, or any other Thrift Store you can find around your area.

READ MORE..




The Open Mic Talent Scouts

WHAT

You're going to Hollywood... district

Watching up and coming talent can be fun (or not). Sometimes though, it's even more fun to "get in on the performance" aspect of things and be an observing talent agent, looking for the next major star.

You and your date will find a suitable seat, get out your notebooks, order a beverage or two, and then start deciding who's fame-worthy, and who needs to keep their day job.

WHEN

Thursday? Tuesday? When's an open mic?

If you have a comedy club in your area, they will no doubt have an open mic night.
They tend to be on the less-busy nights, but there's usually no cover charge. Get there a little early though, just in case.

WHERE

Comedy club, Jazz bar, Music venue?

If you're not already abreast of the local spots to watch strangers perform what they believe is talent, hop on to Gewgle and see where any "local comedy" or "open mic night" are.
Once you've found one that suits, the rest is ... well, the rest.

READ MORE..




Tinder, Tequila, & Too Much Fun

WHAT

Fun and making-Fun of stuff!

Post up at a bar or some other agreed upon spot, pop open your Tinder app, and start co-swiping with your date.

WHEN

The earlier, the better...

Honestly, the earlier you choose to do this will probably be proportional to the success/fun level.
Later times are usually busy. Busy means loud. Loud sucks for trying to crack jokes and make fun of weirdos on dating apps. If possible, pick a time either early in the evening if it's a weekend, or choose an off-night like a Tuesday or Wednesday.

WHERE

Anywhere's fine, as long as they've got WiFi

Truthfully, you could probably just use your mobile data if the wifi sucks...
But aside from that, any bar/pub/brewery will do! Just replace 'Tequila' with drink-of-your-choice.
Extra points if you keep the alliteration.

READ MORE..




I Don't Karaoke How Bad You Are

WHAT

Step 1. Pick a song. Step 2. Embarass yourself?

Even if you're not a good singer, there are ways around this. Bob Dylan songs for instance. Or songs that are intentionally done bad (Backstreet Boys, NSYNC, etc).
However, the easiest genre to do in my opinion, is rap.
Rap is the easiest Karaoke option to be "good-shitty" at. Singing, on the other hand, you have to be somewhat in-tune, find spots to breathe, use proper inflection, etc. There's a lot to think about with singing while with Rap, you can just basically talk in a structured cadence and people will be ok with it. With Rap, as long as you know (most of) the words and have a (somewhat) steady cadence... easy, done. I'd suggest "old school" songs as well like Warren G - Regulators. This is a crowd favorite from what I've experienced. Everyone knows it and it's not too difficult to perform.
Are there any songs you can think of that would make a "good" karaoke option? My personal favorite is SkeeLo - I Wish. (feel free to steal that one and use it for yourself--another crowd pleaser that poeple will sing along during the chorus with)

WHEN

I've got 1 kitchen table and no Microphone...

Unless you've got your own Disco-Tailgate rig, you are (like many of the other outings) limited by the hours of operation for said-business. Pro Tip: Check Google, or, you can use the "Find A..." option to search for "Karaoke" in your zip code or city.

WHERE

Hey Siri... Where can I Karaoke?

Unfortunately, Karaoke isn't like a dance battle where it could just go down at any time, any where. Granted, you can invest in a portable/home karaoke machine and take the party to your place. Heck, you can even just search on YouTube for "< song name > karaoke" and you'll find an instrumental/karaoke version that you can sing along with.
But, short of running a Speakeasy-style Karaoke club out of your domecile, you may be relegated to searching the internets for available options.
You can use the "Find A..." feature and search for "Karaoke" in your zipcode or city to find places that are rocking mics and melting faces.

READ MORE..




21st Birthday Mulligan

WHAT

"I'm older, wiser... and my friends can actually afford to buy me drinks now!"

It's fun to pretend to be 21 again. And if anyone gives you a hard time about it, tell them to "F off, I identify as a 21 year old tonight."

WHEN

Before 2am?

Honestly, any day is great. Doing it on an actual birthday is a little better, but definitely not required.

WHERE

The more laid-back the bar, the better.

You can suss out the vibe of a venue the moment you step in. You probably already have a good idea of the spots that are chill and the spots that are... well, not. Either pick a 'home base' or use the Pub Crawl method. Either way, really any bar will suffice.

READ MORE..




Pre-Funk Before The Pool... Hall!

WHAT

"I get really good between beers 2 and 3..."

Bars often offer FREE POOL on certain days. To encourage more degenerates to come in and drink during the early afternoons, bars have taken to offering things like “free pool” on Sundays & other typically “slower” times.

Find a place you enjoy that has a pool table (and NOT a pool league that night) and possibly some beverage options.
If you're too cheap to buy a couple drinks, you can pre-funk in the car and 'babysit' a beer the rest of the evening.
You may need a bunch of quarters as well..

WHEN

Consider the 'off-night' times...

A number of bars and taverns will offer free pool on Sunday afternoons or Wednesday nights or some other typically slow day (the bar is trying to drive business in on an otherwise crap night for them).
See if there are any places in your area that offer free pool and consider settling in there.
Another (half decent) option would be to learn to pick locks and take the glass guard off the table.
Either way.

WHERE

Bars or Billiard spots

As long as they have a(n available) pool table and a cue or two, you're pretty much good to go.
Now, add in a little 'social lubricant' aka alcohol and you can loosen up and have some more uninhibitted fun.

READ MORE..




International Airport Olympics

WHAT

People watching games at the International Airport

There are multiple mini-games that fall into the entirity of the International Airport Olympics. Just lkie the olympics has multiple events, so does this.

Baggage Claim Psychic
This game is points based. You and your date mosey on down to the baggage claim and post up in an inconspicuous spot. Wait around for a flight to get in and the bags to start rolling down the conveyor belt.
Your goal: match luggage to travelers.
Each time your correct (which is not that often), you get a point. These tend to end a lot like soccer games (low scores, ties). But oh man.. when you get one right... it's time to gloat.

Then, once the losses are too much to bear (because again, unless you're a real psychic, matching luggage to travelers is NOT an easy task), it's time to move over to a security checkpoint and play "Bigger, Better, Backstory"

Bigger, Better, Backstory
This game is all about crafting a story about a person's life who you presumably know nothing about. The idea is that you give a potential detail about the intended target, and then your date "Yes, And's" you and gives another detail.. but just a little more fantastical. Each additional detail should get more and more incredible until you move onto the next person. Then, you can continue to interweave and bring back in previous "characters" and stitch together back-stories for the entire airport population.

WHEN

Fly times at the airport lounge

The airport doesn't close. They're open 24 hours a day (well, except some of the businesses inside--they close).
You can really choose any time you want, but here are a few tips that may come in handy:

  • When are a bunch of flights coming in?
    You can look up arrivals/departures on the airports website iirc. You don't have to get this granular, but you can check out to see if more flights seem to get in around one time or another
  • Plan on grabbing a drink or bite to eat?
    If so, then you should probably rule out certain times when those restaurants will be closed. Also, consider what is OUTSIDE of the security checkpoint. Unless you have a ticket or a way past TSA, you are pretty much relegated to the food/drink options in the general area of the airport. Don't fret though, there are going to still be at least a few places to choose form.
  • Where are you going to park?
    It'd be a good idea to get an idea of the parking situation prior to going. How much is short term parking? Do they take credit cards or cash only? Are you carpooling or meeting each other there?
    All pretty simple things, but it'll make you much more comfortable and relaxed when you already have an idea of how things are going to work--it's why performances have dress rehersals.

WHERE

.... the airport, duh

Granted, if it's a small or private airport, this doesn't really work. The people watching and the food options will be nil, so best to stick to the large airport (especially the international) variety.
If you aren't sure where the closest airport is to you... I wouldn't even suggest Google'ing it--I'd tell you to just not do this.
You must live hours from an airport, so this will become anything but a cheap date if you were to follow thru. haha

READ MORE..




Make-Shift Ice Cream Shop

WHAT

An Old-Fashioned Date With A Frugal Flair

Because lines at ice cream specialty shops tend to be long, sometimes you just want to get your treat and get on with the date. Patience is a virtue, but standing in line with someone you might have just met for the first time can be a bit of pressure. So, make it easier on both of you and skip the line entirely. Find a nearby grocery store (or even a 7-11 in a pinch) and head over toward the freezer section. There you'll find a variety of (probably overpriced) ice cream to choose from. If you're trying to keep it cheap, you can grab a single half gallon (oddly enough, generally cheaper than the specialty pints) of one flavor... or neopalitan if you're trying to be extra special. BUT WAIT! you're not done yet. Don't make the mistake of walking out of the store without AT LEAST some plastic flat ware or spoons for eating said ice cream. You could even go a step further and grab some Chinet bowls

WHEN

Ye Olde Ice Creame Shoppe... has short hours!

One of the bvest things about grabbing your ice cream from the grocery store is that most of them are either A.) open late, or B.) potentially open 24 hours.
For this reason, you can pretty much do this date whenever you can make it to the grocery store (or again, a 7-11 in a pinch... they have a small assortment of ice cream and it will due if you are just trying to fulfull your legal obligation to the date you outlined for your potential-partner.)
Play it safe and just check the hours of operation, but like I said, you're probably going to be fine at virutally any time.

WHERE

Does this town even have an ice cream shop?

What about a 'Shoppe'?
Even in a one-horse-town, there's probably a grocery store that has ice cream for sale. If listening to John Mellencamp has taught me anything, small towns ALL have a "Tasty Freeze" where Jack & Dianne will be sucking on chilli dogs.
Ultimately, you can probably leave it up to Google to figure out4 where the nearest grocery sotre or establishment that serves/sells ice cream is.

READ MORE..




Bar Hopping Scavenger Hunt

WHAT

Photo-Scavenger Hunt where the first to send the pic gets a point

The rukes are pretty straightforward and simple:
Find each item on the list, take a picture of it, and text it to your potential-partner before they text you.

This game requires you to have exchanged phone numbers (scoooooore!).

    Items To Find & PicMsg:
  • #7 Billiard ball
  • Half-empty beer glass
  • Parking meter
  • Toothpick or Mint
  • Graffiti on a bathroom wall/stall
  • Napkin with a name or number
  • Picture with a Bartender
  • Event flyer / promo poster
  • Dog
  • Numbered Street Sign
  • Tree
  • Batahroom mirror selfie
  • Hand Sanitizer
  • The word "Pub"
  • The word "Tavern"

Each item is worth one point. Have the least trustworthy person keep score.

WHEN

You don't have to go home... but you can't photograph here

As long as you start prior to last call (and you're a total night owl I guess), you can make this work just about anywhere. Obviously the easiest time to do this would be some sort of business hours that facilitate photo taking.
Example: If you're a shy person to begin with, you might not feel totally comfortable snapping random pictures. You might be the type of person who is constantly thinking, "...are people lookoing at me? Do they think what I'm doing is weird? Oh shit.. do they think I'm like a spy or something?"
So, if you're one of those people who (like me) is constantly "in their head" about stuff, you may want to choose hours/days that are traditionally not as packed. However, if you're a fan of people-watching, you may want to hit the peak hours where you have prime viewing.

WHERE

The Bar, Bitch!

The name sort of implies the location of the outing... so, if you didn't pick that up by now, well.. this one probably isn't for you (and this whole series of cheap dates probably isn't for you either come to think of it... no refunds, though.)

READ MORE..




Schizophrenic or Bluetooth Headset?

WHAT

Are they talking to themselves or someone on the phone?

This shouldn't be that tough... right?
If you see a bluetooth headset, you can pretty much make that call. However, it's not always that easy and they may just be a crazy person WEARING a bluetooth headset. For that reason, you and your date should try to determine A.) Who they're talking to -- it could be a business call or a direct line to Jesus. B.) Why they're talking to them -- closing that Ferchetti deal or channeling a long dead relative? That's up to the two of you.

WHEN

Arm-Chair Psychologist with FREE Diagnosises!

People watching games are good for virtually any time, any place. They're a great option to kill time or help break the ice.
Waiting for a table at a restaurant? Play some people watching games! Stuck in line for a show? Play some people watching games! There is really no "bad time" to play some people watching games. The stakes are low and you can quit/start/pick back up any time.

WHERE

Here, There, Everywhere...

Since crazy can strike at anywhere and at any moment, this is one of those people watching games that you can play... anywhere! Granted, it's better to play this game out in public (where you'll actually see people) than alone in your house or apartment. But, that's your choice. You make the game as "easy" or as "hard" as you want. For me, I generally have a few of the people watching games in my head for different types of places. When all else fails, just go for a walk downtown (on a sunny day) and you'll see a whole heck of a lot of people that you can creepily stare at and assign some made up motives and character traits to!

READ MORE..




Matchmaker, Matchmaker, Make Them A Match!

WHAT

A Match Made In He....LL.

You're creating the backstory. Make it an entertaining one. Did one of them just get back from living overseas, helping children in an under-priveledged country? Is one of the people a professional gold-digger and is waiting for the other to write them into the will??
There are no wrong answers--just have fun!

WHEN

You never know when you'll meet 'the one'

They say you find love when you stop looking for it... but I think it's better to take your chances and just keep looking.
So like looking for love, you can (and should?) probably play this game all the time. Failing that, it's good to play any/some of the time. That's one of the great things about people watching games; you can pretty much start, stop, and pick them back up whenever you feel like.

WHERE

Somewhere public... probably?

People watching games require people... to watch. There's generally not a whole lot of strangers available to creep on in the privacy of your home, so it's best to get out if you plan to play this one. A park, a bar, a festival, or even just a walk downtown. Any place where there's going to be a lot of interesting people to obvserve is a good choice.

READ MORE..




Shitty City Chauffeur

WHAT

Bus fare for 2 and a medium bottle of hand-sanitizer

A ride on the bus isn't too terrible when you've got great companionship or at least some weird people to watch.
Take a nice loop around your city with your own (public) driver. And to further pass the time, there is a list of items you should be trying to locate.
Basically, if I-Spy was on the bus... which is what you'd be doing.

You get the idea..

WHEN

How late do the busses run? (and how safe is your city?)

I think the busses around me run until 12:30am most nights. Your town's public transit may differ, so besbest to check your city's website or transportation provider to get accurate times.
You can probably Google-maps the bus route around your city and see the approx. length of time it takes to make the full round.

Might want to get an idea of this beforehand, just in case...

WHERE

Right here... well, there.. where ever you are

Bus, subway, train, etc. Probably not a viable idea to play inside an Uber or Lyft... but if you've got the money to burn.. the private experience might be that extra wow factor that will really impress your date. However, considering this is CheapSkateDates, I don't think the private-cab thing is a smart way to redistribute your wealth.
You may consider what the safest route is, or secondarily--the most scenic route--to take.

READ MORE..