LOSING MY VIRGINITY TAUGHT ME TO TRUST THE TIMING OF MY LIFE
When I started writing this essay a few years back I opened it by calling myself a “late bloomer." I think I've written the same in past newsletters, but in reality, that's not a title I actually identify with. The label “late bloomer” implies that we have all agreed to operate on the same schedule in life. I certainly made no such agreement. There are people who find success at 25 and people who find success at 55. Some people start a family at 21 and others do it at 40. I would love nothing more than for all of us to find acceptance in the fact that we don't have to play by culturally prescribed timelines, because each of us has our own timeline, and no one is better or worse for reaching a milestone before anyone else.
My first real kiss (if we don't count a silly game of spin the bottle) was the night before I left for my freshman year of college. The guy attended my rival high school, but I would always see him around town, often outside of a local salad spot that my friends and I would go to. I couldn't tell you how many times I went there just hoping that I would see him. I had been crushing on him all summer, and he finally asked me to hang out two days before I was leaving for school. I have little memory of the actual date, but I know we ended the night kissing on the trampoline in his backyard. I was not in any rush to lose my virginity, even though most of my friends had done IT by the time we graduated. I always assumed I would wait for my first long-term relationship to have sex for the first time. I'm a true romantic at heart, so I wanted it to be meaningful and all the things that losing your virginity typically are not. But I actually enjoyed being a virgin—it felt like a secret source of power. I was in complete control of whether I would do it and with whom.
The first time I attempted to lose my virginity was the summer before my junior year of college. The guy wasn't actually my boyfriend but a friend with benefits that felt as close as I was going to get to a boyfriend at that time. We'd known each other for about a year, talked every single day, exchanged music, had inside jokes, and sleepovers. A part of me definitely thought if we had sex, it would get him closer to being my boyfriend.
So, the stars felt like they were aligning when he invited me to hang out with him and his friends during his summer trip to New York City. I decided this would be the opportunity to take things to the next level. It wasn't so much about me dying to do the deed and rid myself of my “innocence,” as I think I viewed it as an opportunity to be closer with him. I hooked up with other guys in college, but I never really considered losing my virginity to any of them. I was clearly craving more intimacy with someone I had feelings for—not considering that sex would never equal intimacy in this equation.
When we got to the pivotal moment after a few margaritas in SoHo, he told me he didn't have a condom.
What? This wasn't part of the plan or the fantasy.
We were staying in a hotel that I had stayed at a few months prior for a friend's birthday, and I knew there was a box of “essentials” in a drawer that contained condoms. I could easily solve this conundrum, but something in my mind told me to just leave it alone. So, I didn't say a word, and we just went to sleep instead.
The start of the school year was imminent, his senior year and my junior year, and there would be plenty of opportunities. If it was meant to happen, it would happen.
It didn't happen.
Come September, he met a freshman girl, and within a few short weeks, they were boyfriend and girlfriend. I was devastated. This guy I had been putting in all this work for was dating someone who wasn't me?
And as if that wasn't painful enough, his new girlfriend was determined to banish me from his life completely. Like a page out of a teen novel, she started spreading lies about me. She told him that I was being mean to her, giving her dirty looks in the hallways, talking about her in the cafeteria loud enough for others to hear. My FWB even confided in one of my friends about my supposed behavior, and she almost believed it too.
None of it was true.
I was pretty devastated by it all, not only losing someone who I very desperately wanted to be my first boyfriend, but also someone who I felt was a friend. I started therapy for the second time around because I had such a hard time getting over the situation. At that age, I had little understanding of my emotions and how to stop them from swallowing me whole. And it was really still too early to decipher any kind of dating pattern—I was just a barely twenty-something-year-old experimenting and figuring things out.
Nevertheless, I graduated from college a virgin.
Once I made it to New York City, navigating the hook-up/dating scene as a virgin also felt complicated. You meet someone out, have a fun night, and don't want that night to end—so I'd go home with a guy or bring them back to my apartment only for them to express their disappointment when I would tell them I wasn't having sex with them—and I really meant it.
One night I went home with a club promoter (yeah, I can't believe I'm admitting that either) who had been pursuing me relentlessly for weeks. I was tipsy and accidentally let it slip that I wouldn't sleep with him because I was a virgin. “Are you serious? You're lying,” he said to me. But when I doubled down, he immediately rolled over and went to sleep. I later found out that he told one of our mutual friends I tried to have sex with him.
Eventually, my virgin status just became a bit of a drag. It wasn't so much that I felt pressured or left out compared to my friends who were enjoying the full range of sexual experimentation—I just got to a point where I didn't really know what I was actually waiting for anymore. What was the value in holding onto my virginity? I'd been very aware of my sexuality and desires, but I think I was also stuck on making the “right” decision—and my fears about getting hurt. So, I came to the conclusion that I didn't want to give a man so much power over me. If I was still waiting for my first *real* relationship, when it inevitably ended, I would always have him on a pedestal with a gold medal for being the first man to deflower me.
I met him as I was leaving the Jane Hotel after a night out with friends. I was walking down Greenwich Street to hail a cab home when an occupied taxi cruised by me, heading towards the Jane. Seconds later, I heard a guy yelling as he jumped out of that same cab and ran towards me. He asked me why I was going home and begged me to come back to Jane for a drink. I tried to play hard to get for all of one minute until I obliged.
It was his second night in New York and he was visiting from Sweden, he told me as I had one more drink with him at the bar. Afterward, he walked me back outside to get a cab and kissed me. He made a sweet attempt at trying to invite himself home with me, but I told him I was going home alone and he could call me tomorrow.
He did call the next day, and we met up that night with our mutual friends and bar hopped around the Lower East Side and Chinatown. That night, I did allow him to come home with me. It wasn't premeditated, I didn't look at him and think, okay, this is the one. I don't really know what it was. There was just an instant connection and ease between us—and part of me just felt I might miss out on something really special if I didn't give myself to the situation.
And my intuition was right. The next 8 days with him were unlike anything I had ever experienced at that point. We saw each other every day, and he was loving, kind, and genuine. It was a stark contrast for the majority of my hook-up experiences which seemed to have a 24-hour expiration stamp. No guy had ever treated me as adoringly as he did. I can still vividly remember our walk to Cafe Gitane for breakfast the morning after with our arms around each other—feeling high on oxytocin. I didn't tell him I was a virgin until the night before he left to go home. I don't know why, I just didn't want it to be a thing. But the pain I felt when it was time for him to return home to Sweden was also overwhelming. I was flooded with that panic of, how am I ever going to find someone like that again? (Spoiler alert: I've met many men that have felt just as special as him since then). While I had this really beautiful experience, I was also confronted with the loss and what could've been. If only he lived here, if only I could get on a plane to visit him.
He eventually returned the following summer, and we had another two weeks to make more memories. He stayed with me, and it felt like we were a couple. We hung out with my friends, went to Governor's Ball, I took him to all my favorite spots, and we even celebrated Swedish Midsummer together at the Bowery Hotel's infamous party. I wanted to visit him in Stockholm, but at that point, I hadn't been on a plane in years—so it didn't seem feasible with my plane anxiety.
But later that year, as I got more opportunities to travel for work, I made the conscious decision to get over my flying anxiety and apply for my first passport. The next summer, I finally made it to Stockholm with one of my best friends. I stayed with him, of course, and we went back to playing house as a loving couple. When we parted ways, we went back to our regular lives again. We kept in touch and would Skype here and there, but there was no making this a viable relationship—although I absolutely toyed with the idea of what it would be like to move to Stockholm.
This relationship changed me on many levels. To this day, I still look back on that connection and feel really lucky. I'm grateful that this person and I found each other, if only for a short while. And I think about how things could've gone so much differently if I had slept with my college FWB right before our friendship imploded.
As women, we face so much pressure to hit a multitude of milestones by certain ages—and losing our virginity is perhaps the first on this imaginary timeline because of the idea that it must be done by the "right" age, not too early but also not too late.
Sure, most people would consider losing your virginity at 25 as late, although now, it's actually a lot more common than we know to be a virgin in your twenties or not have had a serious relationship in your thirties. It's just that no one talks about it because we've been made to feel that it's somehow shameful or that these are our “red flags." But who's to say it's actually “late” or that I was a “late” bloomer? I made decisions that I felt were right for me when I was ready to make them—I wasn't playing by my friends' rules or society's rules. And I wouldn't take back the experience I had for anything—nor have I ever felt that I missed out on anything by waiting. This was truly one of my biggest lessons that, sometimes, when we don't get what we *think* we want, it's because we deserve something better.