Your bag is empty.
Welcome to Playboy Undercover—where our anonymous columnists give you a peek of what’s really going on, well, under the covers. From the curious to the downright kinky, our guides are pulling back the curtains on desire. Wanna invite us undercover? So long as it’s between two (or more!) consenting adults, we’re game. Send your story to [email protected].
I am 38 and I still haven’t had my first kiss yet —which means yes.… I am a virgin too. I’m not panicking about the situation, I think that experiencing romance is something that can still happen for me, but as of right now, I don’t have a dating life. I work the night shift in a grocery store, sorting stock in the meat section from Monday to Wednesday. The shifts I work makes it hard to date because I’m usually so tired and struggle with my sleep a lot.
I try to focus on my work but it’s difficult not having been kissed. It’s on my mind all the time — I have seen my friends find boyfriends and girlfriends, get married, have kids, get divorced, find new partners. During all this time I have remained single, not by choice. I have never explicitly told my friends that I am a virgin. I have never mentioned any dates I have been on, but from time to time, they will ask me if I have found anyone yet.
I’m not saying I’m handsome: I’m not tall, 5’4”, and a little bit fat, but when I say that to people, they tell me I’m not. I guess my clothes hide it. My hair started thinning when I was 22, but the situation is not so bad. When I look in the mirror I can’t see it myself, but my friend Jon always winds me up: ‘do you not get annoyed that you’re bald?’ To be honest Jon, I don’t remember the problem until you mention it every time.
In everyone’s life there are these moments early on that help you gain confidence: maybe you ask someone out. You take risks even if you are ultimately rejected to learn these lessons. But for me, they kind of never happened which has been this knock on effect up until now. When you lack confidence in yourself, it just puts a stop to all possibilities. Sometimes I see a pretty woman and I think ‘am I good enough for her? Am I brave enough to go up to her?’ It scares me to even try as I think everyone is out of my league.
I remember my first crush, Kelly, in middle school. She was a little plump with curly red hair, and wore black boots with heels. Kelly lived on the same road so we would get the bus together to school. I didn’t know a lot of girls, so when she was nice to me, I automatically thought it would be nice to have her as a girlfriend. One day she hinted that she was into my best friend, and liked another guy in my class too. I felt devastated. That’s twice that I was not the one chosen.
My younger brother got married when he was only 22 and I was 26. It had been a snap decision as his girlfriend got pregnant. I felt jealous being the older brother, and he was taking these big life steps before me.
Ten years ago, my parents tried to set me up. The landlord of my dad’s restaurant, where I worked in high school, had a daughter about my age and the landlord said that we should meet up. My parents took her phone number and were encouraging me to text her. Me being me, I didn’t know what to say. I introduced myself and said our parents want us to date. Probably scared her off. As a teen, working at the restaurant kept me from social situations, like school dances. It was my choice, but now I think I missed out on some key life experiences.
Like everyone, I’ve tried dating apps but I feel I got burned. It’s not the place for me. I would match with women but they’d never really talk. There was one woman, we started talking daily for a week and then started texting each other. She would send me pictures of her dog, what she was eating, and we talked about our work. She was pretty, seemed tall in her pictures with long black hair, her face was half in shadow.
She started talking about investing for our future together. Crypto of course. She wanted me to sign up for some investment scheme, and I refused. She’d say, ‘I’d send you nudes of me if you buy crypto.’ But I unmatched and blocked her.
From then on, I kind of felt suspicious of women who I matched with, thinking that they might also be scams. Why waste effort getting to know someone, messaging back and forth for a week about our lives and waste all my effort for what ends up being a romance scam? I still feel scared trying to get to know someone and it ends up being a fake thing that they are just trying to use you.
A few years ago I was put in the friendzone. The main pull to Shana was her looks. She was a little shorter than me, pretty, and has nice boobs. She was fun and I wanted to make her my girlfriend. Sometimes we would hang out and there’s no space to park in town, so we park near this graveyard. It gets really dark around there, so at night she would hold me really tight, and scream because she was scared. In little moments like that, I imagined her hugging me.
Shana made it clear we are friends and nothing more. Back in the day, no matter how much of a good time we had, I always had the disappointment that we still weren’t together. Now we just enjoy time together and don’t have that expectation. It took a long time, at least five years.
I find little gestures romantic and I’d like to do that for someone one day. The other day I saw a couple sharing an ice cream in the park. Even just holding hands and sitting down on a bench somewhere in the park, chatting about trips we would like to take together, things we could study and improve on ourselves. Maybe I can get married. I enjoy singing and would learn a song to sing for her at the wedding. If it’s our honeymoon, somewhere with a beach hot sun with the waves in the background. She probably would be in a bikini and I’d bring her a cold drink, and we spread sun cream for each other. Someone told me that my love language is acts of service.
When I can’t sleep, sometimes I walk into town and have those moments where everything around me is quiet and start imagining things. Now I’m 38, if I find someone I would like to enjoy dating before getting married, but I’m also nearly 40 I need to think about children. I would like to have a girl and a boy.
If I had a son in my situation I would tell him ‘if you have a crush, just go for it.’ Don’t miss the chance like I did with Kelly. I would encourage him to make more friends, enjoy all experiences possible. Good and bad, these are opportunities to help you grow as a person. I am hopeful that I’m just a late bloomer and I can still experience romance with someone one day.