Unique Date Night Ideas in Cleveland

3 sample itineraries loaded with unique date ideas for Cleveland

You finally have the date that you’ve been looking forward to! You go through your checklist, hair finally behaving: CHECK, perfect fit of your attire: CHECK, shoes that match your whole look: DOUBLE CHECK, fun date planned to make the night nothing short from magical: CHE…check??

As much as dinner and a movie is a classic combo that has survived the ultimate test of time, it’s time to spice things up a little. You don’t really want them to feel like the date is another wave of dejavu.


I mean, no disrespect to the classics, they are classics for a reason, but when it comes to planning a date you have those precious few hours to make the best out of it… and you really want to add a little something special! Here are a few date night ideas Cleveland has to offer and just fun, weird things to do in Cleveland.


Itinerary #1- For the Casual Date

The one place that has been buzzing in Cleveland is Perplexity Games. Rated as #1 Escape Room in Cleveland by TripAdvisor, they provide a series of theme-based escape rooms. Imagine both of you stuck in a room (wink wink)……using your imagination and ideas to get the creative juices flowing.

Getting a room before getting a room, if you know what I mean!

They provide several escape room options to choose from such as: ELIOT NESS, CLOCKWORK CAPER, T.I.T.U.S. and an option which is for fans of the Christmas season, called THE NAUGHTY LIST.

An Escape Room date is the perfect opportunity to see how your partner reacts in challenges (do they become bossy, passive, panicky, or just brilliant) which may add to the reasons for having butterflies in your stomach.

You never have to worry about having an awkward silence during your date, which is probably one of the scariest feelings during a date. (that and finding out your dated is a wanted serial killer)

You’ve got the adrenaline pumping, your date is having a blast and your confidence is through the roof!  Keep the ball rolling. So, where do you go next?

To fuel up of course. Get food……and booze.

Valerio’s Ristorante in Little Italy offers delicious food and a cozy environment to keep the date flowing well.

Valerio’s Ristorante in Little Italy

A 5-minute drive from your fun-between-4-walls adventure, to this cosy place gives you the perfect opportunity to get the conversational sparks flying, bringing lights to the streets of Cleveland!

Can you feel MY excitement talking about YOUR date?

You’ve started the date with the highlight and now you’re mellowing down, starting to share things and getting to know each other. Try to absorb as much information about them as possible, such as their taste in movies!

Aut-O Rama Twin Drive-In has been around since the 1965. The set up is really cute and VERY Instagram worthy.

drive in theater clevelandOkay, okay..I know we’re back to dinner and movie but I told you…you shouldn’t beat a classic, just add a little twist to it.

Itinerary #2- For the FIRST Date

Just typing those words out made me cringe thinking about my first date. I did everything possible to pretty much embarrass myself (I even dipped my bread in the water instead of the soup..oh God!) The worst part was there was no place to hide or anything to cover it up, I mean seriously..what do you do with that??


Reading that, you’d probably take my next suggestion seriously.

Dinner in the Dark, Cleveland’s latest foodie fascination, brings together six different chefs each month, cooking together, often for the first time, at different restaurants.

YOU WILL NOT EAT IN THE DARK, although that would have came in handy for my first date.

But the highlight of this concept is you’ll not know the menu till the event takes place. Exciting, no?

It also takes the pressure off of deciding what to order (we’ve all been in that battle!)


Keep the date on their toes with some mystery and excitement at Perplexity Games Escape Room!

proposal escape room cleveland There are quite a few options for which escape room you would want to roll the dice on and all have different themes. It’s also set for group tasks which means you’re bound to look smarter than a few people (heellooo shining moment!) and score more date night points!


Once you manage to escape the room (bring a sleeping bag in case you don’t) hit memory lane with Superelectric Pinball Parlor!

There’s something about the sound of pinball machines that brings out an almost magical feeling. This would also be a perfect time for you to do a cute bet that always turns out to be a great story at parties (all I have is my bread in water story, I kinda like it though)




Itinerary #3- For the love veterans a.k.a Married Couples

When was the last time you were out at the park doing NOTHING? Well, I’m here to tell you to kiss goodbye to the date nights where you had the same food at the same restaurant on the same day each week.


Start your evening with the calmness and the much needed serenity at the Cleveland Botanical Garden.

I mean, I feel like you’d need convincing to leave that place more than to go there. After a long romantic stroll and many unphoto-bombed pictures, have a nice ADULT dinner.


Where? Here….

The Flying FigJust look at that. The Flying Fig pride themselves with locally sourced food, innovative cocktails, and an ever-changing wine list. I love everything in that sentence. The perfect clean-cut setting somehow manages to channel a very welcoming and romantic vibe. Sparks WILL fly!.


Done with food? Time for some challenges to make the night a little more fun.


Perplexity Games Escape Room it is! You’ve survived marriage but can you survive working together to try and escape the room? It would be the perfect opportunity to see just how well you both work as a team and how lucky your are to marry a fun loving person that is still (will probably always be) young at heart. I guess two IS better than one, huh!

Clockwork Caper at Perplexity Games escape room ClevelandReady to go home after?

OF COURSE NOT…you don’t have a curfew anymore guys..

Clifford House Bed & Breakfast is literally two minutes away and also GORGEOUS!

I think you can figure out what to do next……have a well rested sleep. (sure!)


So, if you’re looking for date night ideas in Cleveland or just inspiration on how to plan your date night, hope this helped.

Classic with a twist! Have a great date!!


Start Your Date Night With an Escape Room Adventure!!