Dating, oh dating. You are such a strange phenomenon, so amazing & simultaneously horrifying. Who knows where the night will begin or where it could all lead? But here’s the kicker — dinner & a movie is totally played out. You’re interesting, they’re interesting — surely that’s not the best you can come up with! So here, for your romantic pleasure, are a list of 50 unusual, interesting, fun ideas to try!

Wake up at 4am & watch the sunrise together
Maybe not first date material, but perhaps third or fourth. What could be better than sitting close on a rooftop somewhere, talking & laughing & watching the sun come up? Take a flask of hot coffee for extra points.

Have an extravagant brunch at 8am
Get dressed up & do breakfast properly. Make a big deal out of it, & include fabulous pancakes, decadent waffles, poached eggs & the best hollandaise. Boutique hotels often do a brilliant brunch, but a bit of surreptitious googling should set you on the right track. Thick white linen napkins first thing in the morning are a magnificent way to start the day — & then you can either go your separate ways, or take a walk.

Go to an art gallery on a Saturday afternoon
You’ll learn a lot about the person you’re standing next to if you go & check out art together. Plus it gives you something so much more stimulating to talk about than the last episode of The Bachelor!

Bring half an evening
One person organises the food, & the other organises a movie, or one person organises tickets to an amusement park, & the other plans a walking tour. Very collaborative! You get the opportunity to impress your crush with your superior taste while also finding out more about them. You don’t have to meet at someone’s house, either — a park bench, good picnic spot or even town square could work too.

The double-Netflix date
For those of you not in America, Netflix is an on-demand DVD rental service that the entire country seems to have a subscription to. Sorry to be so geographically-specific, but “double-Netflix” rolls off the tongue a little better than, “Let’s just each bring a movie & subject one another to our extremely questionable taste”!

The Case Of The Mystery Band
Grab a copy of your local newspaper or magazine, close your eyes, run your finger over the “live music” section & choose a band neither of you have ever heard of to go & see. It could be amazing; it could be completely hellish — you won’t know until you go! But even if it’s shocking, it’s definitely a bonding experience, & maybe even something to tell the children, eh?

Make a fort
Enough said!

Bring your favourite book & read the first chapter aloud
Again, this says a lot about a person. Will they bring The Witches? Lolita? The 120 Days Of Sodom? I can barely stand the suspense…

Mix CD trade
Are mix CDs antiquated? Maybe you could just make one another a playlist on your iPod or something… Either way, sharing & discussing music is one of the world’s great, little-known aphrodisiacs. Truth. (Unless all they listen to is Richard Marx. Damn.)

Do something neither of you have done before
Pottery class? Swing dancing lessons? Hiring a moped & driving out into the country? Who knows, but it’s nice to share an experience that is new to both of you!

Random restaurant date
Search Yelp for restaurants in your area, close your eyes, roll your mouse & point at the screen. Just like the mystery band date, you never know how it’ll go — it could be a hidden treasure or a total health hazard, but that’s part of the fun, isn’t it?!

Hot air ballooning
Not the cheapest date idea, I’ll admit, but certain to score you points & to impress your lover-to-be. Maybe if you’re an heiress?!

Decorate a Christmas tree together
Yes, this one is seasonal, but think how fun it would be! It’ll cheer up your (or their) apartment, give you a visual reminder of them (assuming the date goes well), & maybe you could even go ice-skating afterwards. Cute ++.

The Sunday New York Times crossword date
Bonus: intellectual stimulation, nerd points & you get to find out how clever they really are, all in one fell swoop. & wouldn’t it be great if you looked at them across the table, sunlight falling across their face, & they smiled at you & you thought, ‘I would like to spend every Sunday this way’? Yes. Yes it would.

Playground date
Slides are exciting. Monkey bars are fun. Swinging side by side is totally awesome, & you can have a contest as to who can swing higher. (Hint: if you are younger you will probably win this one. Older people, I have learned, sometimes feel motion sick on swings. Definitely one of the downsides of maturity.)

Tree-climbing date
No explanation required, but if you take them to a secret treehouse that no one else knows about, please don’t be surprised if they propose on the spot!

Video game arcade date
This isn’t always a perfect match, especially when it comes to girls in high heels & those weird shoot-em-up zombie games. Or whatever. (How impressed would you be by a drop-dead gorgeous girl kicking immense zombie butt, though?) But everyone likes air hockey. Don’t they?!

Ye olde photobooth hunt
Trawl your city for old-school photobooths & take as many strips as you can. Take props, maybe a silly wig or two, & see how bizarre you can make them. P.S. Photobooth.net is your go-to source for major photobooth info!

A drive-in movie
I admit, this one seems ultra-cool to me just because I’ve never done it & I am in love with Danny Zucco from here until eternity. Just don’t try to take your ring off by wiping it through your greasy hair & hit your girlfriend in the boob!

Sugarhigh date
Simple. Go to a convenience store. Buy cheap, evil, sugary treats. Find somewhere to sit & glut yourselves on them. Then see what happens. Spontaneous dancing? A completely misguided shopping trip? Leapfrogging over small children?! Let us know!

The socially irresponsible date
One word: graffiti. You rebels!

Pretend to be tourists
Go & do the stuff you’ve never done because, well, you’ve always lived here. Wear a baseball cap, khakis & a bum bag (“fanny pack”) for a feeling of real authenticity, & don’t forget to take plenty of photos!

“My old neighbourhood” date
Walk around the area you used to live, & tell your date about where you used to ride your bike, what happened on that one lawn, which house was best to hit up on hallowe’en & who the really creepy neighbours were.

The really long one-way walk
No rules except that you just have to walk for a really long time in one direction & not turn around. When you’re really exhausted or you hit the ocean, it’s time to go back. Catch a taxi or a bus or something to ease the pain.

Take a dog for a walk
It doesn’t have to be yours, or even hers. Borrow your friend’s dog! They’re adorable & fun & will give you something to talk about if you get stuck. Plus, people will come up to you & say, “Cute dog”, & you can beam at each other like proud parents.

Go to the beach
Take music, towels, a big floppy sun-hat or two & enjoy the day. Build sandcastles, put sunscreen lotion on one another, go swimming & then travel home together as the sun is setting, relaxed & happy.

Karaoke!
I love karaoke. I love karaoke. I love karaoke. Again, it’s a great way to get to know someone — you’ll instantly know how outgoing they are, how much they like a challenge & what their music taste is like. Plus, usually in my experience, a day-glo private room & weird drinks are part of the package. Who could say no to that?

Collaborative art date
Get a canvas or even just a big piece of paper, some paint, pencils or pastels, & go nuts.

Walk around to different bars & tell stories about what happened
This one is kind of odd, but I was once on a date with a guy where we went to three different bars & as we walked around, he told me about the strange & hilarious memories he had associated with those places. It helped that he was cute & a good storyteller, but still, it could work.

Go & listen to jazz
Aka, pretend to be sophisticated. Or actually be sophisticated, depending…

Take cameras & explore an abandoned place
An excellent opportunity to be artsy-fartsy, or if you like to be on the other side of the camera, get them to take photos of you pulling your most beautifulest face!

Medieval Times
Oh geez, does this need any explanation? No! Eating with your hands, handsome knights, silly hats? Sign me up!

“First date” night
This one works best if it’s not your actual first date. Like, for example, you’ve been together for 3 years & live in the same house. Get dressed separately, meet somewhere strange & a bit awkward, & pretend you don’t know one another. Start from scratch. Ask all those banal questions you’re supposed to ask (“So, what do you do?”). Then at the end of the night, rejoice that you’re in a relationship & not dating any more!

The generational date
Pretend you’re an age that you’re not, then act accordingly. A senior citizens date might involve going lawn bowling, making apple sauce & watching The Price Is Right. A teenager date might involve roller-skating, making out in public & drinking vodka in an alley-way. You get the idea…

The recession date
Triple B’s: eat at Burger King, take the bus to get there, then go & play bingo. Maybe you could go window shopping afterwards or huddle around a cigarette for warmth (very Withnail & I).

The silent date
In a loud, noisy, overstimulating world, it can be nice to unplug & escape. But it can be nice to do that with your new favourite person, too. Hold hands & read books on a wharf & occasionally look adoringly at one another. Cool.

Make cupcakes together
You know you want to.

Make a video & put it on Youtube
You could really do anything & make a video of it, but it does at least give you a purpose & a goal. Plus, later on you have a record of what went on — & a slew of idiotic comments to wade through. Haha!

Liveblog your date
Upload pictures, tweet it, even give it a hash-tag. #evan&madelinesfirstdate. Cute.

Travel without going anywhere
The premise is simple. Have a normal date but speak with an accent. You both have to do it, by the way, or it doesn’t count. Choose something difficult for extra hilarity points, like Scottish or South African. Och aye!

Write letters to one another & post them
Maybe if you were on a date with a contender for Macho Man Of The Year this wouldn’t work, but I think it is almost the cutest idea ever. It’s definitely worth a try.

Dye each other’s hair
There’s nothing like a radical change to make life more exciting. Try blue-black or red or even pink! I wrote a how to, so there’s no excuse!

Sneak into a rooftop pool
They often have them at hotels, but they are usually only open to guests, so you might have to use your best sweet-talking skills, but it will be totally worth it if you can swing it. My suggestion? Just act as if you’re supposed to be there, & them questioning you is really just a waste of your time. Be charming but efficient. Godspeed!

Jump on a trampoline
The hardest part will be finding one, but I have faith in you!

Use sparklers to draw each other pictures
& maybe even write “GD + MK 4 EVER”. (Take photos.)

Ice-cream parlour
Get a really, really, really big sundae & split it. Bicker over toppings. Then, when you’re done, find somewhere to lie down & talk about how sick you feel. A bonding experience to be sure!

Have a five-course dinner… at different places
Have an appetiser at one place, soup somewhere else, a main here, a dessert there, & coffee at your favourite cafe.

Play truth or dare
Awesome.

Three-hour make-out session
Choose a good location & use a stopwatch if necessary. Sounds like a good way to spend an afternoon to me!

Photo by Janneke Storm.