It’s that time of the year again, the leaves are changing colors, coffee shops around the city are unleashing a line of pumpkin flavored goodies and, oh yes, it’s Cuffin’ Season. For those of you who are unfamiliar with the term, it describes that time of year when everyone seems to be coupling up due to the cold weather. And boy can it get “oh so cold!” when you’re newly single and not too familiar with the confusing and sometimes, insecurity inducing world of dating based on likes and swipes.

It’s been two months and eight days since what seemed to me like the most traumatic break up of all time. In between crying and watching reruns of Sex and the City. I decided maybe it’s time to put myself out there again. Now of course if you’re a modern woman the first thing you’re thinking is, “Duh! Go on tinder and find someone”. Unfortunately, at the prime age of twenty-six I still believe that the best way to find a guy is to directly reach out to him. Please note: I was terribly wrong.

A few weeks ago, I had a couple of drinks with my lady friends and mustered up the courage to text a guy I had a crush on, mind you, I had only met him briefly in past, but that didn’t matter. I texted him saying, “I want you! Now what are you going to about it? Only this guy, we’ll call him, Modern Man wasn’t picking up what I was so forwardly putting down. In the moment, I didn’t realize that the rules had changed and random drunk texts are not only desperate, they are more embarrassingly, outdated! Being the understanding guy that Modern Man is, he let me down gently. He told me “he wasn’t looking for anything serious” and kindly accepted my apologies with a “we’ve all been there” laugh. Like I said, it can be oh so cold when you’re newly single in the city.

Being the overly ambitious and determined girl that I am. I didn’t give up so easy. After all, I wanted to spend lazy nights watching Netflix with him and maybe even tag along to one of his softball games. More importantly, I needed him to fill the void left by my dreaded ex-boyfriend and nothing was going to stop me from ensuring that I “cuff’d” someone before it was too late.

I played it “cool”. I didn’t text him for a couple of days in hopes that he’d come crawling back. Except he didn’t crawl back and I found myself wondering, “what the hell did I do or not do?” then in typical single girl fashion I went borderline crazy googling everything under the sun about men, how they text, how they act and if it was possible for a man to like you even if he acts like he doesn’t like you. After reading several posts that blatantly suggested that there was no way on earth this guy could possibly be interested in me. I still, somehow, convinced myself that my Cuffin’ Season crush totally liked me back and all I had to do was stick it out.

This made me want to contact him more. I found myself needing to talk to him. I sent him Facebook messages like, “Oh hey, can you read something I wrote?” or “Know any good songs to listen to when you’re going through a break up?” You know typical needy girl stuff. Until I finally won him over and we ended having a long talk… about the girls he really wanted to date. He put me in this strange place, a place I had only heard people mention in passing… that’s right, I was put into the “friendzone”. He’s actually quite easy to get. Just not by me.

This was a huge blow to my newly single ego. I needed to do something quick or risk running back to my dreaded ex-boyfriend. I finally caved and joined Tinder. And to be quite honest seeing so many guys and being able to pick and choose without any care of what that person might think of me really helped my self-esteem. I even got quite a bit of matches. Then I was left feeling like, “That’s it. Now what?”

Then one of my “matches” sent me a message. He seemed nice so I messaged him back. To my surprise, I’m more confident about putting myself out there than I ever thought. When he asked to take me out on a date. It finally dawned on me that I really wasn’t ready. Not ready to have a man in my life again. Not ready to devote my time to building a relationship. Just not ready to do it all over again, just yet.

I’ve now come to terms with the fact that this year I will be spending Cuffin’ Season cuffed to my sofa with Netflix, a glass of wine and some dependable girlfriends. And for once, I’m starting to feel like that might just be okay.

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