Chapter 1: It All Started With A Boy…

Dating is the oldest art form in history, starting with the careful selection process, to scrupulous courting, to the grand finale, we’ve all mastered, at one point of another, the tumultuous, uphill battle of finding someone to spend more than 20 minutes with us, by their own accord.

Dating in notorious cities filled with good-looking, successful, ambitious men? Going to the locations you read about on gossip sites, filled with paparazzi and a lack of inhibitions? It is as thrilling as all the TV shows and movies make it out to be. Salacious, drama filled, and full of suspense, theatrics, and unnecessarily poignant romantic gestures.

Personally, I try to date as often as possible, of course staying within the carefully outlined criteria I’ve set for myself. How successful are most of these dates? Well, let’s put a few things into perspective first before answering that loaded question.

I date in LA and New York. I’m delusional in almost every way. I never deny the accusation that, often times, I’m not all there. The men (unsuspecting victims), whom I inadvertently lure into my trap with feminine wiles and momentary sanity, are all too willing to go along with this insanity. They pursue me with this obsessive intent to “fix me” which always works to my advantage.  And unfortunately, the same thing tends to happen, time and time again.

I’m in my early 20’s, incredibly confused almost always, and constantly in pursuit of the greener pastures. My Therapist Says gets a lot of dating questions submitted into their dm’s and they’ve asked me to chronicle my unhealthy love life and misadventures with athletes, actors, financiers, and unemployed sociopaths, all who’ve been genuinely kind people.

So, to get back to the question of the success rate of my dating life, I think you can deduce by the confident tone with which I write this that, yes, it’s been GOOD. My goal was never to get a boyfriend, settle down, and move onwards and upwards, yet somehow that’s always where they see us going. My friends often ask me- how does it happen when, of us all, I seem to want it the least? How do I happen to put myself into situations that look and sound straight out of a movie? Well, of course my resistance to it is an integral reason. But it also has something to do with the ‘manic pixie dream girl’ myth, setting people’s curiosity alight if she really turns out to be as good as she is written about.

In my case, I sincerely hope that turns out to be true.


Kyle is an actor you may have seen in numerous TV shows, best friends with probably one of the hottest actors in a Superhero franchise film, and somebody who himself has a deep inferiority complex because of his intense daddy issues. These are just a few things that define Kyle. At this point, of course, I was unaware and blissful.

He asked me out one night after meeting me at this club we frequented; a private, entertainment industry, exclusive venue that I somehow weaseled my way into, every weekend.

He was exactly my type: tall, sexy, self-deprecating, and incredibly well read. I felt as though I’d hit the jackpot with him, and genuinely saw this going the long stretch. We spent fifteen minutes making eye contact with each other across the room, until, finally, a mutual friend had miraculously introduced us. I would come to learn that nothing with “Kyle” was an accident, or miraculous.

“I would be honored to take you out, properly, if you’d give me the pleasure,” he asked, in his British accent, straight out of a Jane Austen novel. It took me less a second then that sentence had come out of his mouth that I was ready, willing, and completely available. To him, however, I took the appropriate pause to consider it and really mull it over: do I want to go out with this beautiful British specimen who chose me in a room full of girls openly ogling him?

“Sure,” I heard myself say, cool and even toned, impressing even myself. The tingling butterflies and excitement of a new crush race through my body, and for the first time in a while, since I broke up with my ex, I felt like I was ready to give it a go again.

We smiled at each other like teenagers for a while, a quick, biting rapport filling in the silence of the obvious sexual tension.  He’d tell me a personal fact laced with some sarcastic remark, that would become his trademark defense mechanism, but for that night, it was perfect. I would reciprocate with same vague, made up fact of my own, acting both the pursuer and the pursued.

Everyone in the room had come, at one point or another, over to tell us how great we looked together and how much of an attractive pair we made. After the appropriate time, we snuck out to the smoking patio, and, watching him lazily light his cigarette, dangling from his lips, looking up at me through his eyelashes, I realized I really liked this guy.

He blew out some smoke, looking every bit James Dean, leaned in, and gently kissed me. In that moment, I felt every fiber of my being come alive. Tobacco and Givenchy cologne surrounded me, and I had to restrain myself from grabbing on to him and pulling him in tighter for a more lasting kiss. He moved his head back a bit, to take another puff, and his bright blue eyes just watched me, reminding me of that awkward teenager who was too scared to make eye contact with boys lest they read every thought running through her mind.

His gaze never faltered once. And, for as long as I had the liquid courage, I tried to maintain the faulty eye contact, breaking every now and then to look down, or towards the street, at his shoulder; anywhere to give me a reprieve from his knowing gaze.

And when I would remember him, I would always come back to that moment and how it defined us and our dynamic.

…to be continued next week

By: Jen


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