How to do a penny date.
A penny date is a date with no destination. You travel to an intersection, flip a coin, and let it choose the turn — heads right, tails left. You do that an agreed number of times, and wherever the last flip leaves you is where the date happens. Here is how to run one properly, including the parts nobody tells you about.
No penny on you? The flips are free here, and the app keeps count of your turns.
Flip a virtual pennyWhat you need
- Two people — or one, but arguing about whether that counted as an intersection is half the fun.
- A coin, or the virtual penny if the couch has eaten yours.
- An hour or two. Twenty turns on foot is a very different evening from twenty turns in a car. Plan the loose end of your night, not the whole of it.
- A way home. The one piece of planning a no-plan date genuinely needs.
The penny date rules, step by step
Agree on a number of turns
Settle the turn count before you leave, because it is the only thing that decides when the date starts. Twenty turns suits a dense city grid, fifteen suits the suburbs, ten suits open country roads. Say the number out loud and stick to it — renegotiating mid-route is how a penny date turns into a drive to the usual place.
Pick a starting point
Start from wherever you already are. A grid of streets gives the coin more to work with than one long road, so if you have a choice, begin somewhere with intersections close together. Starting from your own front door is traditional and requires no planning at all, which is rather the point.
Flip at the next intersection
Travel to the next intersection and flip there, not before. One person flips for the whole date, or you alternate, but agree which before you start so nobody is quietly re-flipping. In a car, the passenger flips. Always.
Heads turn right, tails turn left
That is the whole rule. Going straight on is not an option, which is what keeps the route wandering instead of drifting in one direction. Some people invert it — tails right, heads left — and it makes no difference at all, so long as you decide before the first flip rather than after seeing it.
Re-flip anything unsafe or illegal
If the coin points at a no-turn sign, a one-way street running the wrong way, a private drive, or anywhere that simply feels wrong, that flip does not count. Carry straight on to the next intersection and flip again there. The coin is a suggestion; the road signs are the law.
Stop when the turns run out
Wherever the last turn leaves you is the date. Look around, pick the most promising thing within a short walk, and go in. If the answer is a residential street with nothing on it at all, see what to do when the coin lands nowhere — it happens, and it is entirely salvageable.
How many flips should you take?
This is the question that decides whether your penny date is charming or exhausting, and the answer is entirely about how far apart your intersections are. City blocks arrive every ninety seconds; country crossroads arrive every few miles. Same number of flips, wildly different evening.
| Setting | Turns | Why |
|---|---|---|
| Urban | 20 | Short blocks and frequent corners. Twenty turns can still leave you within a mile of home, which is fine — you will have seen streets you have driven past for years. |
| Suburban | 15 | Longer blocks, cul-de-sacs and curved streets that eat turns without covering ground. Fifteen is enough to get properly lost in a subdivision. |
| Rural | 10 | Miles between junctions. Ten turns on open roads is already a long drive; twenty would be most of a tank of gas. |
If you are walking, treat those numbers as a ceiling rather than a target — ten turns on foot in a city is a comfortable hour. Penny Date sets these counts for you when you choose a setting, and the Advanced option takes any whole number from 1 to 100 if you would rather decide for yourself.
The situations the rules do not cover
Every penny date runs into at least one of these. Settle them now, rather than standing at a junction litigating it.
- A dead end or cul-de-sac
- Turning into one costs you a turn and gives you nothing back. Treat a dead end as unavailable: ignore that direction, take the other one, and count it as the turn. If both directions are dead ends you are already in a cul-de-sac — walk back out to the last real junction and flip there.
- A parking lot, a driveway or private land
- Not a turn. Parking lots in particular will swallow a penny date whole, because they are full of things that look like intersections and are not. Stay on public roads and paths, and never follow the coin onto private property.
- A no-turn sign or a one-way street
- The sign wins. Carry on to the next intersection and flip again there. Do not re-flip on the spot — re-flipping until you like the answer is exactly how you end up at your usual bar.
- A roundabout or traffic circle
- A coin has two sides and a roundabout has more than two exits, so a flip cannot decide it. Number the eligible exits in the order you would reach them after entering, leaving out the road you arrived on, then pick one at random. Penny Date's Advanced mode does this for circles with two to five exits.
- A T-junction, a fork or a five-way
- At a T-junction the coin still works, because there are exactly two ways to go. At a fork or an unusual junction, agree the numbering out loud before you draw — left-most is one, then round to the right — and then draw. Agreeing after you have seen the result does not count.
- A highway on-ramp
- Skip it. A penny date that ends up on a highway is over: the next junction is fifteen miles away and you cannot turn around. If the coin points at an on-ramp, treat it as unavailable and take the other direction.
- Ending up somewhere you have already been
- Perfectly normal, and not a fault — random walks loop. Keep going. If you cross your own path three or four times in a small area, add a couple of turns to break out of it, or agree that the next flip sends you straight on for one block.
- Anywhere that feels wrong
- Leave. No route rule outranks either person's judgment, and either of you can end the date at any point without needing to give a reason.
Four ways to change the game
On foot
The purest version, and the one where a bad landing costs you nothing. Ten to twelve turns in a walkable neighborhood, and you can duck into whatever you pass. Bring water — the coin has no interest in whether you are thirsty.
By public transport
Flip at each stop rather than each intersection: heads means stay on, tails means get off. Or flip at interchanges — heads takes the line heading one way, tails the other. It works beautifully in a city with a decent network, and it caps the cost of the whole date at the fare.
By bike
Somewhere between walking and driving, with the advantage that you can double back when the coin sends you somewhere dull. Keep the turn count nearer the walking number than the driving one, and flip while stopped.
Time-boxed
Instead of counting turns, set a timer — thirty minutes out, then stop wherever you are. Useful when you have a hard finish, and it removes the temptation to add "just three more turns" when you do not like where you have landed.
Doing it safely
Traffic law always beats the coin. Signs, signals, road markings and property restrictions are not inputs to the game. Where the flip conflicts with any of them, the flip loses.
The passenger flips, never the driver. If you are driving alone, park properly before you touch the coin or the phone.
Tell someone, and keep a way home. The point of the date is not knowing where you will end up, which is precisely why somebody else should know roughly when you will be back — and why you want enough fuel, charge or fare to get home from anywhere.
If you are meeting someone for the first time, this is not the date for it. A penny date works best with someone you already trust, in daylight or on lit streets.
What happens when you get there
The last flip is not really the end of the date — it is the start of it. Sometimes the coin drops you outside a good bakery. More often it drops you on a residential corner, at a closed garden centre, or in front of a strip mall with a nail salon and a phone repair shop, and the date becomes what you make of that.
That is the part worth preparing for, and it has a page of its own: penny date ideas — what to do wherever you land, including the plan for landing precisely nowhere.
Common questions
What are the rules of a penny date?
Agree a number of turns before you set off, travel to the next intersection, and flip a coin there: heads means turn right, tails means turn left. Repeat until your turns run out, and wherever you finish is the date. Any turn that is unsafe or illegal does not count — carry on to the next intersection and flip again.
How many turns should a penny date be?
Match the count to how far apart your intersections are: about 20 turns in a city, 15 in the suburbs and 10 on rural roads. On foot, use roughly half those numbers. Any whole number from 1 to 100 works if you would rather choose your own.
What do you do at a dead end or a no-turn sign?
Treat that direction as unavailable. Take the other one and count it as your turn, or if neither direction is possible, carry straight on to the next intersection and flip there. Never follow a flip into a parking lot, a driveway or private property.
How do you flip at a roundabout with more than two exits?
A coin cannot answer a question with more than two answers. Number the eligible exits in the order you reach them after entering, excluding the road you came in on, then choose one at random. Penny Date handles traffic circles with two to five exits in Advanced mode.
Can you do a penny date walking or on public transport?
Yes, and both are good. Walking, use about half the driving turn count. On public transport, flip at each stop or interchange instead of each intersection — heads stay on, tails get off — which caps the cost of the whole date at the fare.
Do you need a real penny?
No. Any coin works, and no coin works too: Penny Date flips a virtual penny in your browser, keeps count of your turns, and tells you when you have arrived. It is free, and there is nothing to install.
Ready? Pick your setting, and let the coin take the first turn.
Start a Penny DateFurther reading: The Penny Hoarder's write-up of the penny date.