My first date with a real human occurred almost exactly a week after I’d lost my virginity to this person (yes, after). We’d met at a bar through a mutual friend, but the attraction didn’t immediately blind us both at first sight. My feelings for her were like a slow burn; I gradually felt that ache of longing you experience after you meet someone new, when you’re hoping that they’ll finally be the one to transform your entire existence. No matter how content you are with your life, sometimes you just want to take the backseat for a while and let someone else show you a new way to live. That’s how I felt when I met Ari.
Ari and I were talking at the club for a while with our mutual friend when she blurted out, “I wouldn’t mind taking you home with me.” I was in trouble. I’d never been “home” with anyone before. It wasn’t my lack of trying, or a lack of interest on the other party’s side. I’d just never truly felt that the stars had aligned for me to experience that fateful night when my virginity would be cast aside like a baby tooth along with the last vestiges of my childhood. Also, no one had ever been so direct with me before, and since I’m terrible at navigating flirtation and small talk, Ari’s language was both shocking and wildly attractive.
So, I said yes. And so did our mutual friend.
My first date with Ari actually came one week after our steamy lesbian threesome. As much as I’d like to say that my previous “experience” with her had diminished the wall of awkwardness between us, I can safely say that our communication directly following was minimal at best, until Ari reached out a week later to ask me out. Lesbian threesome or not, I was new to sex and dating and this was going to be my first date ever, so it’s no wonder I was lost and completely terrified.
We met on a Friday night at a martini bar in one of the more “sophisticated” neighbourhoods in our city. The conversation was easy, the drinks were delicious, and I was actually having fun. Ari’s intelligence and self-confidence were intimidating, but not in a completely unapproachable way. My naivety made me feel childlike next to her, but she seemed to find it endearing.
That night, I said goodbye to Ari without going home with her. I remember mumbling something like, “I don’t usually do that kind of thing,” as if trying to justify our first night together. She probably chuckled at that, and looking back now it certainly seems like a silly thing to say after the fact. But Ari wasn’t deterred by my flippancy.
We went out again the next week, only this time we met at her apartment beforehand for some wine and TV. I went to her apartment with the full expectation of what was going to take place, yet in that moment I felt strange. I kept thinking back to the first night we met where instead of asking myself “why” as I so often do, I settled for “why not” and went home with Ari her on a whim. Why couldn’t I summon that spontaneous part of myself this time? Was this what I really wanted? Was I even that attracted to Ari?
After I deflected her many advances, we ended up at a Mexican restaurant nearby. Again, the conversation was easy: Ari and I opened up to each other about past mental health struggles, which is something I’m rarely open about with anyone. All the while I could tell she was eager to take me back at her apartment. I wanted to share in the feeling, but something was bothering me.
My first date with Ari actually came one week after our steamy lesbian threesome.
All of my doubts emerged at once and I couldn’t seem to drown them in alcohol or puffs from a joint like I had before. I hated myself for not feeling overwhelming desire toward this woman with whom I had already shared a few life-changing experiences, sexually and otherwise. When we were finished with dinner, Ari pointed out that I should pick up the restaurant check since she paid for the wine. In that moment, I felt embarrassed, almost ashamed, that the check hadn’t even crossed my thoughts. My mind began racing with tangential ideas and concerns about the complexities of life and gender politics in general, as if I were trying to distract myself from the most pressing issue at hand: Ari, the woman seated in front of me. The guilt overwhelmed me and yet I found myself back at her apartment, attempting to recreate some of the passion from our first night together.
Compared to how I felt the first night Ari and I slept together, my self-consciousness was tenfold. Was it our mutual friend’s absence from the night’s activities that made me feel off? Or was it the lack of copious amounts of booze and pot? I started to regret ever going to bed with Ari in the first place. Opening up and sharing such an intimate part of myself with someone else felt like a major commitment I wasn't ready to pursue. I felt selfish and cold. I should want the closeness and companionship, I thought. Ari was wonderful, yes, but for whatever reason it didn’t matter to me in that moment.
I stopped things when I realized it would be equally as selfish to continue on with Ari while my heart and head were obviously not in the right place. That night, in Ari’s bed, I broke it off. I can’t even remember what I said to her, but knowing me, it probably involved a lot of rambling about my inability to connect with people and my lack of experience; these excuses, while not untrue, still seemed laughably pathetic in the moment. Ari was shocked. She asked me to come back to bed, and when I refused, she said, “I should’ve pushed you more.”
Now, her words shocked me. What did that even mean? Pushed me more... into sex? Out of my comfort zone? I laughed sadly at her words, not knowing any other way to react in that moment. Ari told me I might as well sleep over since it was getting late, and I wouldn’t have to worry about her trying anything with me again. I believed her. She was still a genuine person, after all. I wasn’t so sure I could say the same about myself after what I had just done.
I settled into Ari’s bed for a good twenty minutes before I decided to leave in the middle of the night. I wasn’t even sure how I was going to get home, but I knew that I couldn’t sleep in that bed beside her. She lived close to a bus shelter so I headed in that direction. I was visibly upset and dishevelled: As I was crossing the street, a stranger started singing “pretty woman, walking down the street...” and smiled kindly at me. For some reason, that small, random gesture made me feel better about everything. I don’t think it was his intention to objectify or harass me, as is the case with many late-night encounters with strange men on city sidewalks. To be told that you’re beautiful is, at the appropriate time, a beautiful thing in itself.
It’s hard to look back on a disappointing moment in your life and realize that you may have been at least partly responsible for your own undoing. Today, the memory of that random stranger still makes me smile, and I still cringe when I think of how things ended with Ari that night. For whatever reason, I readily accepted the surface-level attention of that stranger and yet I rejected Ari, someone kind and open-minded who actually wanted to get to know me. I tried to pin my rejection of Ari on a lack of attraction or spark, but now I better understand the genuine terror I experienced at the thought of her getting close to me. Today, I still feel more relieved than remorseful that I didn’t pursue things further with her.
Much time has passed and I haven’t been on a single date since. I’ve realized there’s a part of me that doesn’t want to be loved because to be really loved means also to be understood. I don’t know what I’d say to Ari if I ever saw her again. I’d likely apologize, although I don’t know exactly what flawed part of myself I’d be apologizing for. It was my first date, or first couple of dates, that showed me just how much I have yet to learn about myself. My experience with Ari shed light on the parts of myself I still need to learn to accept and love. Maybe if I ever saw her again, I’d thank Ari for this instead of apologizing.
Visual and Performance artist Olivia Jane Huffman exposes misogynistic fantasies embedded in our accepted behavioral norms and damaging propaganda. She assembles found materials with sentimental or historical context to critique social injustices. Olivia Jane is the Founder of LADY ART NYC and is based in Brooklyn, NY. More of their work can been seen on their website or Facebook.
This essay and artwork is shared in collaboration with It's Not Personal, a growing anthology and collective that creates opportunities for women to share their dating experiences in a positive environment. The project aims to progress society's conversations around singlehood, relationships and everything in between. For more information, be sure to follow It's NotPersonal on Instagram, join the Facebook group, and send art and writing submissions to email@example.com
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