The Guy’s Guide to Unconventional Dates

Dating should not be burden. Nor should it be boring. For those serial daters, or simply those who are seeking that right person, the regularity of getting to know someone and seeking a relationship can start to feel monotonous. Similarly, if someone in particular catches your eyes, you may be wise to try and set yourself apart.

This is not to say that there is anything wrong with simply hitting a bar and having drinks; after all, the drinks will always be fine and the food will always taste good when you have a fantastic first or second date. Ultimately it will come down to the people involved and how much they click.

There is much to be said though, about breaking free of convention, of making a date not simply an opportunity for you to show your best side, but a chance to be curious and challenge yourself to an extent.

Now, when it comes to shaking things up a bit, we’re not talking about grand gestures or crazy getaways or elaborate events. It’s more the minor tweaks that make a night interesting and mutually beneficial, with the goal to be just a bit less defensive and a bit more engaged with the world around you. We’re not reinventing the wheel here: it’s putting yourself in a situation where you can still get to know someone, but in an environment that fosters better discovery, inwards and outwards.

Thus, here are some literal examples of metaphoric tweaks to liven up the dating experience.

Go on a Crawl

Not actually crawling, but literally, yes, keep moving. Be it a bouncing around to pub or on an art crawl, allow for different scenes, different people, and different atmospheres to excite the night. Changing scenery helps keep the conversation fresh, lest things become a bit awkwardly quiet at times, and also allows for the two parties to get to know each other a bit better through the shifting background. Physically changing positions is a plus too: maybe you’re face to face at a table for a bit, and then you’re walking side by side, and later on sitting next to one another at a bar or tucked away at a corner. If you’re feelings are changing over the course of the night, perhaps too should your actual position.

Take to a Different Kind of Movie

Get away from mainstream movies and big cineplexes for dates; it’s such a throwaway early on in a relationship. Instead, go to a single-screen cinema or one that has a stage too, and see something cultish and old. See something where the director or writer will be there afterwards, or where the house with be packed with vocal and lively fans. It makes for a more intimate, more inclusive evening that should lead to more stimulating conversations and probably quite a few laughs.

See a Burlesque Show

Live entertainment to provoke, enamor, and certainly engage, taking in a burlesque show is sure to provide a memorable night. They abound in the city in many different forms, finding makeshift stages in small bars to far grander spectacles on special occasions and even thematic showcases. Burlesque isn’t necessarily a first date option, but offers entertainment, drinks, and conversation. Most notably, the setting will help said conversation move towards things that are likely needed to be discussed when first meeting someone. That is, questions of attraction, identity, sexuality, fidelity, and expectations. These are topics we shouldn’t shy away from, and we shouldn’t hide away from talking about sex either when dating: it’s a pretty noteworthy thing to talk about.

Meet After Midnight

Strange things happen after midnight; that is, fun strange things. The bars are a little hazier, the music a little louder, and people, well, people are a bit more unhinged. All of that makes for two people to be more open to one another, fostering more intimate (not sexual) conversation. Don’t plan for drinks at eight; hit the bar instead at 12:45 and shut the place down. And then head to an after-hours. It’s a metaphorical breaking-free of limitations and convention. Okay, maybe it’s not that spectacular, but to be bound by time is to be bounded by routine; put yourself somewhere unfamiliar, and keep the two of you on the edge.

Be Unguarded

Ultimately, whatever you are doing, go into a date unguarded. It’s easy to say but harder to practice as we are informed by our past experiences and those stories we see and hear from others around us. Going into a date unguarded is to not have preconceptions; it’s about letting a person reveal themselves to you naturally just as you do to them. It means maybe having another drink if you might normally not, it means going somewhere new, and it means allowing whatever standards, guidelines, and rules you normally follow to go out the window (which is not to say lose your morals). It’s about not letting ideas, not letting games come in the way of whatever is unfolding in front of you.

For example, one of my most memorable dates took place in the afternoon at a café. It went so well, seemed so different and unexpected, that it was only minutes after we parted that I thought, why not let us have a second date this evening. And we did; and it was fun and weird and yet seemed completely natural.

So don’t be guarded; be smart and be yourself, and don’t put yourself in a place of discomfort, but let what happens, happen. Go on two dates in one day. Have a date an hour-and-a-half after meeting someone. Go somewhere new, somewhere sexy, somewhere engaging, and you will be surprised what an enjoyable experience dating can become.

Anthony Marcusa is a Toronto-based freelance journalist whose writing dabbles in film, TV, music, sports, and relationships – though not necessarily in that order. He’s simultaneously youthfully idealistic and curmudgeonly cynical. You can follow him on Twitter @MrAnthonyWrites.

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