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  • Writer's pictureTrish

Being a Hopeless Romantic in the Hookup Era


We all know the troupe; the lonely girl in her late 20s to early 30s, sitting alone in her apartment, a glass of wine in hand, mindlessly sobbing over some rom com while she talks to her dog about the struggles of dating at her age. She goes on and on about how no one understands anymore, no one seems to want real, genuine connection. They just want to get in, get off, and get out. She’s going on date after date, some with more potential than others but none of them making it far enough to really stick.


SURPRISE! It’s me. I’m that cliché.


Don’t get me wrong, I talk a big game. After a particularly shitty date you’ll probably catch me strutting around my house, telling my roommates that I’m “of the streets” so, it doesn’t really matter that it didn’t work out because it was doomed from the start anyways. I’ll wave off their condolences and offers of a pep talk while I raise my glass of cabernet and promptly down it as quickly as possible. Anything to take the edge off, right?


To be entirely honest, that worked for a while. Dating can be fun. I love getting dressed up and going out to meet new people. I love the art of flirting and conversation. And, don’t even get me started on the thrill of a first hookup. It’s even extra interesting because I’m bi-sexual and date both men and women. So, the variety of my dates is pretty vast. But, when it comes down to the act of actually connecting? I find my experiences to be lacking.


The truth is that I’m a hopeless romantic at heart. Don’t get me wrong. I love casual sex – when you have an itch sometimes it just needs to be scratched. But, I crave genuine love all the way down in my soul. I want it all. I want the healthy, supportive, beautiful love that Jane Austen only wishes she could have written about. As one of my all time favorite movies put it,


“I want that can’t eat, can’t sleep, reach for the stars, over the fence, World Series kind of stuff.”

(Any It Takes Two fans in here?)


Sometimes I attribute my affliction as a hopeless romantic to being a writer. I’m constantly day dreaming of good stories to tell, a way to spin a moment into a beautiful work of art. You can’t tell me that Nicholas Sparks did not have his fair share of earth shattering love and even more catastrophic heartbreak when his brain birthed The Notebook. But, regardless of the reason – I want love. I love love. I crave love.


When this realization hits you, you start to get into the thoughts of how to navigate it? Especially now, in a world where I can jump on Tinder and schedule a hookup as easily as ordering a pizza. I can get the physical human connection that will trick my brain into thinking I’m being fulfilled, at least for a little while. Then it’s easy to forget about the fact that more than likely, when they leave I’ll be left feeling worse than before they came over.


Since accepting my identity as a woman who loves love, I’ve been doing some brain storming about things I can do to help hold myself accountable and assist me in navigating this journey of being a woman who is a sexual being, who wants casual sex, but also wants to go on a journey to find her soul mate.


1. When the other person tells me that they’re just wanting to have fun and see where it goes, know that it likely means it won’t lead anywhere but to a bed.


I’ve been there so many times before, having someone telling me one thing but me hearing something entirely different and, this is one of those scenarios. If someone says this to you, in my experience 9/10 times it will only lead to casual sex. And, THAT’S ENTIRELY OK. It’s ok if the other person doesn’t want anything serious, as I’ve said a few times by now, I love a good hookup. But, by actively listening and understanding the intention behind statements like this, it will help me keep my expectations for the future more realistic and not get hopeful that it will turn into something more, ultimately leading to disappointment.


2. Be open and honest about my expectations and, my headspace with both myself and the other person.

Since I’m someone that wants both casual sex and a deeper connection, it’s going to be incredibly important to check in with myself before any encounter. Am I in a place to have sex without attachments and not feel shitty about it after? Is there anything additional besides sex, like cuddling, that I’ll need to make sure I’m not left feeling used after the experience? Questions like this are things I will need to ask myself to make sure I don’t end up hurting myself in the long run. And, I also need to be able to effectively communicate these needs to the person I'm going to be sleeping with.


3. Know my deal breakers and when to walk away.


If I go through the questioning above and determine I’m not in a place to hookup without feeling shitty, or, if I’m in a place where I’ll require more after-care than normal, I need to be able to voice that clearly and effectively communicate it to my potential partner. From there, depending on their response, I need to be able to decipher when not receiving that after care is negotiable and when it’s a deal breaker and I need to walk away.


4. Conserve my romantic energy for the relationships where it matters.


I’m a giving person, it’s just in my nature. But, if I want to navigate both hookups and searching for a long-term partner, I’ll need to be stingy with the amount of myself and my romantic energy that I’m pouring into others. I don’t want to be depleting myself for a casual hookup and then leaving myself grumpy for a potential long-term partner. Everyone has their role. My job will be to know it and address it accordingly.

Reading all of this back now, it all seems kind of clinical but, the truth is I think taking a logical approach when considering diving into the deep end can save a lot of unnecessary heart break. I don’t know how all of this is going to go. Since COVID-19 and the lockdown, my dating prospects have been low and things have been primarily virtual but, as things start to open up and I get more comfortable going back out into the world, I’ll need to keep these things in the fore front of my mind and have a lot of check ins with myself.

Being both a romantic and sexual person is going to be just like any other thing in life - take stock of your mental state and your resources, negotiate your wants and needs, and know when to walk away. Who knows if this will work. Knowing me, I'll likely end up still crying into a glass of wine more than my fair share of times but, as I keep telling myself - each failed encounter is just one step to a successful one.

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