Lately I have been obsessing over the idea of dating. I decided last week that I wanted to make the final plunge and just lose my virginity. I’m 23 years old, I live in West Hollywood, why can’t I just casually date and have sex like a normal human being? Very quickly I made it my mission to lose my virginity. I was going to date and, if it felt comfortable and right, I would have sex.
I’ve always been attracted to older men, but I never really seriously considered dating anyone much older than me because of all the obvious reasons- societal constructs, dementia, etc. Recently though I thought, “Why not? If I like older men, why not date older men?” So I did.
The first man I went on a date with last week was 58, a year younger than my father’s age. Now, this is not exactly the first thing I had in mind when I decided to date older men, but he was attractive and he’d asked me out on OKCupid, so I said yes. We met at a café at the end of my street. I was waiting outside for him when I heard a familiar Russian accent saying my name. I turned to see a good friend of mine wearing an apron and carrying several menus. It immediately dawned on me that this was the restaurant that she had told me about working at and that she was going to see me on a date with this man old enough to be my father. “This is a sign,” I thought, but hell if I knew what it meant. She got me a table and my date arrived a few minutes later. We had a very nice conversation, and played a fun little game where he told me what he was doing on the day that I was born. Ultimately though, I realized that I was not feeling a connection, so the next day I told him the truth and we parted ways. I felt bad letting him down, but then again, I always find an excuse to feel guilty.
The second man I went on a date with was a 52 year old man who I’d met at church the week before. It was my second time attending this church, which was The United Church of Christ. He approached me before the service and asked to sit next to me, and we chatted a bit before and during the service. I told him I was from Virginia, and he told me that he went to UVA. I told him that I had as well, and we talked about the University. I mentioned that I had turned 23 on the 6th of February, and he told me that was his birthday as well. I was intrigued by all these strange coincidences, and I found him attractive, so when he asked me out for coffee I said yes. He later called me and amended it to drinks, asking if I was free at 11 pm that Wednesday, since that was when he got done with his last massage client (he was a massage therapist). I told him I didn’t drink but that I’d be happy to meet him at that time. Being lazy, I suggested the same café I’d been to two days before on my first date. “Great!” He said, “I’m leaving from my boyfriend’s place and he lives right near there so I’ll see you then.” I was confused. Why would he ask me, a “hot young single”, out for drinks at friggin 11 pm at night if he had a boyfriend? Maybe he just wanted to be friends? Regardless, I thought he was a nice person, so I was fine with a platonic friendship, although a little disappointed.
We met that Wednesday night, talked a lot about my life, my experiences with dating and how I had been feeling really conflicted about sex lately. I found myself being very honest with him because this was not, in fact, a date like I had imagined in my mind. I found myself being okay with that though and as he walked me home I was glad that we had talked that night. Things took a strange turn when we were at the door of my apartment, however.
“I have a question,” he said.
“Okay,” I said.
“Can I hold you?” He asked me.
“…Excuse me?” I asked.
“Nothing inappropriate. Because I have a boyfriend. I just feel like holding you.”
I was dumbstruck. What? Hold me? What does that mean? Is this real life? I didn’t know what to say.
“Sure!” I said.
“Great!” He said.
I tentatively leaned in for a hug. He didn’t move.
“I’m sorry, how does this work exactly?” I asked him.
“Oh we would go up to your apartment and just sit on your couch and I’d hold you for a few minutes,” he said nonchalantly, as though this was something he’d done a thousand times.
We went upstairs to my room, and sat on my couch. He took my legs and draped them over his, and then held me. I sat there for a while, not really knowing what exactly was going on but actually feeling kind of comforted. I realized that, while this was technically very strange, nothing inappropriate was in fact happening, and I did feel rather soothed.
I asked him why he had wanted to hold me.
“You just seemed like you needed soothing. And I’m a massage therapist- It’s my job to make people feel better physically,” he said.
“Huh,” I said, and he held me for a few more minutes.
“You’re very cute,” he said. “Don’t worry- you’ll find someone you feel comfortable having sex with soon.”
“Thanks,” I said.
After a few minutes I walked him downstairs and we said goodbye. This was by far the strangest date/ not-a-date I’ve ever been on, but it actually made me feel a lot better about myself. Sure, he probably could have chopped me up into little pieces, but so could any man I bring home.
The third man I went on a date with was only 40, and we had met on Tinder. We met that Thursday during the day at the Starbucks at the Ralph’s near my home, because apparently he lived just on the other street near me. He was a DJ, and he had worked on the music for the first 13 cycles of America’s Next Top Model. I was intrigued. We had a really nice conversation about the industry, television, writing, and music. I was still in my “I wanna have sex” phase, so I decided that I would try and lead it in that general direction. I asked him if he wanted to come over and hang out at my place, so we walked over from the Ralph’s and talked about the horror comedy genre while he smoked an American Spirit cigarette. He asked me if it was a turn-off and I said no. When we got up to my room, we sat down on my couch and I draped my legs over his. This time, there was not just holding. We made out and I could taste the tobacco on his tongue. I then realized that it actually is a bit of a turn off to kiss someone who has just smoked a cigarette, but hey- you live and you learn. As we kissed I thought to myself- am I going to do this? Is it virginity losing time? I decided mid-kiss that, no, I wouldn’t have sex with someone on the first date, especially not if I was going to be losing my virginity, so I stopped and told him that I was a virgin. We continued kissing and after he left I immediately regretted not having sex with him.
The next day, however, I thought more about sex. How do I feel about it? What does it mean to me? What do I want it to mean? I asked my parents and my close friends what they thought. It eventually dawned on me, however, that I already knew the answer. I had grown up being taught that sex was about love, and that sex and love go hand in hand. I had thought that I was a weird combination of lustful and prudish, when in reality I was looking for permission to have sex without love. I came to the conclusion that if I could say I’d only ever had sex with men that I was in love with, then I would be happy with the decisions I’d made. I know that having sex doesn’t make me a bad person. I know that having casual sex doesn’t make me a bad person. But I also know that, for me personally, I want to be in love with whomever I have sex with. I want it to mean something. And I think that’s how I can respect myself. Therefore, I’ve decided to stop rushing things. My overactive hormones have been causing me to rush into physical intimacy with the men I date, but I know that the only way I’ll grow comfortable enough with someone to have sex with them is if I take it slow and do it right. So, right now, I’m making a pact to take my time with things. I also realized that I don’t really know the first thing about relationships and sex, so dating men who are twice my age does not really go well with my emotional immaturity. I think I need to stick to dating my peers until I actually decide what it is I want out of a relationship.
So, basically, I’m celibate as a nun and I’m going to die a virgin.