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.
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.
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.
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).
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...
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
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..
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.)
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.
Seriously. My parents used to do this all the time. Granted, they were in like the top 1% for RCI or VI or something, so there was no reason to ever buy into more points... but the presenters never knew that (until the end). That's one way it made it very easy to say "no thanks" to the high pressure sales tactics.
Another way to avoid that is by just being super cheap or poor--you either don't want to afford it or simply can't! Brilliant!
Find a Timeshare presentation that offers a free gift or at least a meal you are interested in, find a date who's game for it, and enjoy! You can even dress up and pretend to be a long time married couple, even if it's your first date.
You're pretty much at the mercy of whatever company is putting on the presentation. It's not like a standard restaurant where you can just call and make reservations for a time you want. You have to be on the lookout for these events and if you see them, make sure to make note of the date & time.
Sometimes you'll get these things in the mail, sometimes you'll find them online, sometimes you'll get recruited by your friends and neighbors. Either way, be on the lookout for these opportunities to get a free meal, gift card, or some other thing of value to you. If you dig around a little, you'll find a whole bunch of these types of events in your area.
We've all put on a movie with no intention of actually paying attention to it. At least this time you can be real upfront about what's going to happen.
The movie is just background noise and a small distraction while you and your date get snuggled up and comfy. So grab some blankets and extra pillows, select a random movie (tip: try not to choose something with a bunch of crazy shootouts or action scenes) and start sawing logs.
I'd like to say that anytime is fine for a nap, but there probably are some times when you should be alert and wakeful. However, once you've narrowed down when you can schedule to be lazy, you should jump on that opportunity. And by jump, I mean fall asleep.
Unless you're a horse or a person with the unique ability to sleep in an upright, standing position... then pretty much any relatively flat, moderately comfortable area that's large enough for 2 will do. Personally, my preference would be to make a "super bed" which is basically just a spot on the floor that you've comfyfied with pillows, blankets, sleeping bags, etc. Granted, the bed or the couch are obviously suitable options as well that require less upfront work.
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.
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!
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.
Using a free wedding registry service like Target.com's, head to a location and grab a hand scanner from the customer service department. From there, you and your date can roam the isles, scanning and adding the craziest items to your list in hopes that some rich wedding guest will buy it for you (or at least look at it and wonder "wtf?!?")
Whether it's a first date or the 14th, you get to image yourselves as if you were gong to get hitched (make up the reason) and now it's your chance to ask for all the crap you can't afford on your own!
I think Target's open til like 11pm in many places. But reglardless, it's probably best to check the store hours first before heading out there. Otherwise you'll have your first nearly-married-fight.
As you can probably tell.... I suggest Target. However, there may not be a location in your area and you can choose something like Bed Bath & Beyond or Macy's instead. All of them should have free services and hand scanners. (it's only fun if you get to goto the store and scan stuff with the laser thing).
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.
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.
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.
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.
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)
Goodwill, Salvation Army, or any other Thrift Store you can find around your area.
There's no way you haven't heard of The Secret by now (or some variation of The Law of Attraction). One of the things they talk about is creating a Vision Board. Think of this like a grade-school collage project where you just cut out pictures of all the stuff you want and words/letters that have special meaning to you. This can be anything from serious to goofy, which is great--it doesn't pigeon hole yourself into some dry, boring blah thing.
So, grab as many magazines and old junk mail as you can, find some old newspapers or cool advertisement flyers and then start cutting up the pieces that make up your future fabulous life.
Depending where you end up going may further narrow down WHEN you do it.
If you choose to spread your art projects out over the tables of a local cafe, great. Figure out their business hours and least busy times, schedule it up & go!
Otherwise, if you plan to make things a little more private, one of your places is probably the ideal situation. As long as there's somewhere to cut, glue, and chat, you're golden.
Once you have your magazines and glue-sticks and such, you can pretty much just post up at someone house--or, if you're a real gangster, a 24-hour diner or Starbucks. Covering your table with magazine scraps and blobs of non-toxic glue are probably not in the restaurant's job description (though that might be nicer to pick up than half-finished pancakes or a picked-apart chicken sandwich.
But regardless of where you choose, as long as you keep it playful, it'll be a fun time.
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)
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)
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.
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.
The idea is pretty simple. You are trying to get the best deal for an item of your choosing. Whether it's a graphic tee or an old action figure, whoever can haggle for the biggest discount is the winner.
Take it a step further and whoever can find the best value, meaning what do you think the owner paid vs. what price did you pay at the garage sale for it?
Final game variation, whoever can get the MOST items for their money is the winner.
Usually, garage sales are linked to "nice weather". No one wants to be walking around in the rain from house to house in your ritsy neighborhood, trying to find bargains.
Most often, you can find listings for garage sales in the newspaper, Craigslist, or on Facebook. I remember when I was a child, we would have a neighborhood garage sale. All the houses around the neighborhood would collectively put up signs around the area and, on the agreed upon weekend, would open their garage doors to any roving weirdos who wanted to see their old stuff.
tl;dr check the newspaper, craigslist, or facebook.
Often times, homeowners will group together and host a neightborhood garage sale. You can pretty much bank on parking your car somewhere in the neighborhood and then walking from garage to garage as you play your games.
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
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 has different hours.
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.
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.
Tongue Twisters are always a fun little challenge that bring back childhood memories. For that reason, they're a good choice as an ice-breaker/conversation piece.
Everyone knows at least one or two tongue twisters, but here are a few the two of you can play with:
Since this is just a little conversation game, you can play whenever you want. It doesn't matter the time (as long as it's not "quiet hours" or something weird). Lull in the conversation? Ask about Tongue Twisters!
There 'where' isn't very particular. As long as you two can hear each other speak, I'd say you're fine. This is good as a "filler" or "thing to do while..". Try these on a walk or drive to your next destination. Times where you want to fill the gaps are the places you can toss in the tongue twisters.
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.
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:
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
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.
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
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.
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.
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.)
The game isn't very hard (pun intended). The idea is simple--come up with a name that could either represent an everyday noun or a stage name for a stripper.
Once you have come up with a name, then decide on what song this exotic dancer likes to perform to as well as the signature move that they do to earn all the $$$ from their sleazey patrons.
Whenever the mood strikes, you can pull this little conversation game out of your back pocket and have a laugh. Since we aren't reliant on business hours to facilitate the timing of this date, you can pretty much just drop this into conversation whenever and let the good times roll!
Since this is a game based on imagination and conversation, it's something you can do virtually anywhere--even online, over a Zoom call if necessary. Granted, a great place for name inspiration would be a strip club... however, that kind of negates the idea of these dates being cheap.
Generally, strip clubs don't appreciate folks who are just here to browse.
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.
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.
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!
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!
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.
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.
I'm always fascinated by the trinkets people make and subsequently sell to some local shop. The idea that so many people had to say "yes" to get this thing from idea to shelf blows my mind sometoimes (especially when the souveniors are absolute trash).
What type of effort do you think went into making said item?
What was the 'chain of command' when it came to getting this product designed and made? Is it a one-person operation, or a sprawling capitalistic venture providing incomes to numerous families?
All of that is up to you!
If there's a shop to buy kitchy shit (and it's open), then your "when" is now. Aside from taking into account business hours and maximum occupancy, you can pretty much just figure out a place you want to walk around and
Beach towns are notorious for having a string of stores that sell nothing but low quality trash. Granted, you don't need to be near the ocean to find a store that totally sucks. There are awful stores everywhere--you just have to keep your eyes open.
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.
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..
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...
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.