Dating and Relationship Advice

I always thought that after losing my virginity, I’d wake up to a different universe—that I would get bigger boobs, have a tight butt, and master every sex position. I’d sit in a big leather chair, smoke out of a pipe, and talk about my newfound knowledge. That did not happen. The universe stayed the same, my boobs didn’t get any bigger, and I still don't know where to buy a pipe.

I was 23 and still a virgin. No, nothing was wrong with me. I still had all of my limbs. I wasn’t a fan of Star Trek, and I admit I did hang out with all the musical theater kids, but they seemed to be doing fine in that department. I was waiting for someone nice. Someone who wasn’t just trying to fuck. Someone who thought of me as more than just a body, and who wasn’t freaked out about my V-card, which most men were. Someone who would text me back and maybe hold my hand in a botanical garden.

Since I didn't lose my virginity in college, and that’s where most people do it, I joined a dating app. I was ready to put myself out there and meet new people, outside of my musical theater friends. I'd soon learn that dating in NYC is a nightmare.

There was Matt 6’2, a muscular blonde talent agent. (I know I’m a monster for putting matches in my phone based on their height, but in all fairness, I’m 5’11 and wasn’t ready to settle for someone shorter just yet.) For our date, we made plans to see a show. He got tickets for free since he worked in the industry. We decided to meet at a bar first to properly introduce ourselves. The bar he chose was located inside Bloomingdales. Yes, out of all the bars in Manhattan, that was his go-to place. It was there that he ordered a Manhattan, trying to seem classy, but I was not fooled. We went to the show, and he bragged about his job, as it slowly became clear he wasn’t actually a talent agent, but an assistant to an assistant of a talent agent.

There was Jack 6’4, who had dark, lanky hair. He wrote for a website and was very funny. We went to a pub and really hit it off. We talked about stand-up, and it was he who inspired me to get into comedy writing. A few dates later I learned he was newly single and not over his ex. We became friends, and years later would still follow each other on social media.

Then there was Tal 6’2. He was Tall and his name was Tal. I am ashamed to admit that at the time I found this to be hilarious. He had brown hair and brown eyes, and a weird mole on his forehead that was kind of cute. I can’t say I remember much about his personality—he was basic but he was kind, which was hard to find. What I do remember is his sick apartment in the village. It had a loft bed and an outdoor space, which is virtually unheard of in New York. I slept over there a few times without having sex, and confessed to him that I was a virgin on the third date. He was cool with it, since he didn’t have much experience himself. His inexperience made me like him more—it also helped that he made banana pancakes for me in the morning from scratch.

We saw each other for about four months, the longest “relationship” I had ever been in. He was my boyfriend. I never told him he was my boyfriend, but he was. I didn’t officially define the relationship because I felt like talks ruined everything. My personal rule was that you are in a relationship as long as no one calls it one, and I didn't want to risk ruining my first one by having the talk.

Tal came over one night after working late. My roommates were in the living room, hanging out with some friends. We chose to go to bed early, like an old couple who just finished watching Jeopardy. I couldn’t sleep because I was filled with energy, so I decided to spice things up and go for it.

It started out awkward, and very vanilla. He clearly wasn’t that experienced, which was partly why I picked him in the first place. The sex was mechanical and felt empty. Nothing like the movies or porn, even. But at least there was eye contact. I felt like a 16 year-old-boy, down for anything but having no idea what was going on. It was like how I imagine most people feel when losing their V-card. First some pain, then disappointment, and then in my case, nothing. I don’t just mean that I emotionally didn’t feel anything—but that I literally couldn’t feel anything.

“I went soft,” he whispered. I made him repeat it twice. Then I realized he went soft… while inside of me. I heard about this happening to people. Not being able to keep it up, getting nervous or worse, not being attracted to the person. When the sex is so bad that it doesn’t stay up. All of these thoughts ran through my head. My auto reaction in these kinds of awkward moments was to just laugh. Probably not the best reaction when someone's limb dick is still inside you. “You are not a virgin anymore but, we didn’t have sex,” Tal said, trying to comfort me. Little did he know that I would have sex multiple times throughout my life without ever really having sex.

The relationship didn’t last much longer after that. Maybe a month, just long enough to blame it ending on something else, but we both knew the truth. You can’t just stop seeing someone immediately after something like that. Take their virginity without really doing it and then bounce. You have to not really "do it” a bunch of times, and then bounce. I am glad I waited for someone nice who made me breakfast. (My standards are way higher now.) But in reality I waited 23 years for someone to go soft inside me.