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?)
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.
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.
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.
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.
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.
Post up at a bar or some other agreed upon spot, pop open your Tinder app, and start co-swiping with your date.
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.
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.
There are a lot of options, but here's a few common ones you should find at most establishments:
Again, like many of the other outings, unless you're skilled at B&E, you'll probably have to stick to regular business hours.
Narrow down the types of games you want to play (for instance, maybe your date is a 1-armed Vietnam Vet... Pool is probably not the best choice in this case)
Instead of waiting for the perfect sunny day and all the other moving pieces to fall into place schedule-wise, consider hosting your picnic in one of the nice office buildings around your area. Scout out a cozy little spot in advance, pack a casual meal or snack, (maybe a bottle of wine?) and bring your date to your weather controlled oasis.
Aside from worrying about business hours (i.e. getting in and not locked-in), the only other consideration I'd advise you on... considering.. is if the area gets busy during a lunch rush.
If that's the case, try to pick an off hour--maybe even an early dinnerish sort of thing.
There are no doubt a local business complex around your area, and the newer they are, the more likely they are to have a nice little "common area" with tables, couches, fake plants, and other stuff to make it seem like it's a nice place... and not just where people goto work.
So, either hit a Google search for business complex locations in your area and go do a little recon. The things I look for would be as much privacy as possible, though this is sort of counter intuitive for these types of areas. However, they do exist, you just have to do a little bit of looking.
And if anyone starts questioning why you're there, just claim to work in the insurance agency--there is ALWAYS an insurance agency in these types of buildings. Claim you just started and that's also why you'll have no other information, probably including the name of the place you just asserted that you're employed at. Oh well..
Other than those things listed above, a simple place to eat/play is really all that you'll need...
..and a blanket or something to sit on to make it pic-nic'y
FILL THIS IN LATER
Ideally, a picnic is outside, but it doesn't really matter. You could even post up in your living room on the floor if it's raining or you're just lazy as hell and trying to score.
Honestly, any day is great. Doing it on an actual birthday is a little better, but definitely not required.
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.
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..
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.
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.
Find a string of pubs/bars that are within walking distance of each other. Verify they all have a similar time-frame for Happy Hour. Map out your route-to-take; park your car at one place, walk to the further bar, and work your way back.
(or call a cab/Uber/Lyft)
Sometimes Happy Hour is whenever you say it is. I mean really, if you think about it, it's basically a state of mind (that also includes drink and/or food specials which happened to be based outside of your mind and within reality).
But all that aside,
You can string together a series of pubs on Google Street View or even use something like MapMyRun to create a "rum route"
Figure out how to make some sort of semi-fancy drink. YouTube has lots of people who fancy themselves the next Tom "Cocktail" Cruise, so let the algorithm guide you down a booze-soaked rabbit hole.
Once you have your cocktail list designed, grab a bunch of mini-bottles from your local alcohol store. I say mini-bottles because we're trying to keep this under $20 without resorting to stealing or breaking the law. Now, re-watch that YouTube video a few more times and memorize the coolest parts. Then, proceed to impress your date while you cue up "Cocktail", conjure up a creative concoction, then curl up on the couch to watch the movie and criticize Cruise's technique.
You set the schedule, you pick the time. Since this is date is either going to happen at one of your places or potentially in the liquor store parking lot while you stream Netflix on your phone.... the idea is you can basically do it whenever. Granted, some pre-planning on ingredients list is suggested, but part of the fun is making the purchase together.
As long as there's cups and maybe a television, you're pretty much set. And honestly, you don't even need the television part. However, it's much better to watch something like "Cocktail" or "Club Paradise" or something in that genre.
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!).
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.
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.)
Instead of trying to get a spot at a swanky rooftop bar and wind up spending a fortune just to get a little tipsy, steak out a high rise parking structure with a decent view of your city. Pack a couple drinks and a delicious snack, park your car at the top, and enjoy!
Short of the parking structure closing and you being unable to enter/leave, twighlight or sunset tends to be the best time for this in my opinion. Granted, if the parking garage you frequent doesn't have a western-facing side (and you are a loyalist to saaid structure), then you'll just have to maybe settle for a view of the lights.
Every downtown tends to have a public parking structure. Some are free, some cost a few dollars an hour, but either way the cost is incredibly low and should be affordable by any cheap-dater.
I suggest getting on Google Street View and scoping out the surroundings of the structure. This way, you can figure out if a Sunset beverage & bite to eat is possible, or if you'll have a downtown-view drink and scope some city lights.