Now all of my friends have been sexually active for years and there’s always been jokes and pressure to get started, and they didn’t really understand my situation. I also work in a workplace — the military — that is the very definition of hyper-masculinity, where there is an expectation to be sexually-active and where I have experienced and witnessed others being put down for being sexually inexperienced.
Here’s the bad part: Recently, on a trip to Europe with friends, we made a stop in Amsterdam and, after a night of partying, alcohol, and a little bit of encouragement from my friends, I slept with one of the women in the red light district. I guess my thought process at the time was that I just wanted to experience sex and see first-hand what the whole fuss was all about. I had also been feeling bad about my past failures and really wanted to get the first one out of the way.
The whole experience, while the woman was friendly and nice and I tried my best to be respectful and polite, was underwhelming and left me feeling terrible. I feel so ashamed over what I have done. The act itself was so mechanical and hollow and devoid of any emotions. I often lie awake in my bed and wonder about what led the woman I slept with to enter that line of work. I know Amsterdam’s RLD is legal; however, I just feel horrible if I took advantage of her circumstances or something like that. I never thought I would be the type of person to pay for sex, and I feel terrible knowing how disappointed and disgusted some people in my life, like my sister and mother, would be with me if they knew. I feel like I let them down, but most of all I let myself down.
The sex was safe, a condom was used for everything, and I tested clean a few weeks after and will be tested again in a few months to ensure I am clean. I just don’t know how I am going to get back into dating after this. I feel like I am tainted or carrying this huge shame around with me and that, as soon as any woman I date asks about my sexual history or first time and finds out what I did, she will be gone.
How should I approach this in future relationships when the topic of sexual history comes up? I just can’t help but feel that this will be a deal-breaker for most women. I can’t justify it to myself, so I would be hopeless explaining it to a significant other. I am an extremely honest person and couldn’t lie. In the past, girls I was seeing never asked but this was always in casual relationships, and I feel that in a serious relationship this is bound to come up.
I think about this daily and it’s really bothering me. I feel like this one act has completely changed my life. — Ashamed of Sleeping with a Hooker
I replied to a similar question here, and I think my response applies to you as well:
Even good people pay for sex sometimes. You can care about people and still pay for the experience of having sex you may not be able to have otherwise. Trading cash for physical intimacy isn’t a symptom of being bad. You know what is? Treating people disrespectfully. Being unkind. Being a racist or a misogynist. Blaming others for your own low self-esteem. Being close-minded. Taking, taking, taking without ever giving back. Hurting people intentionally because you’re hurting yourself and you can’t stand anyone else being happy. And people who are all of these things — even people who are “bad”— are still just human like the rest of us, making mistakes and maybe even learning from them and growing from them.
We’re all on our own journeys, celebrating our own minor and major victories and battling our own demons or insecurities or general shit that gets us down. Most of us are doing the best we can, and some of us are even pretty good at hiding the ugly stuff, the hard stuff, the stuff that keeps us from being the best versions of ourselves we can be. But we all have that stuff. All of us. Every single one of us. So . . . stop being so hard on yourself. Stop beating yourself up for being human and having experiences in your past you aren’t 100% proud of. You are the sum of all of your experiences, not just isolated ones that represent a teeny tiny percentage of your entire history. You are the kindness you’ve shown others and the work you invested in reaching a goal and the moments you’ve fallen a little bit in love with someone you just met. You are the good days and the bad days and the weeks you’ve lost to being sick. You are the races you’ve won and the jobs you didn’t get and the exams you aced after too much or hardly any studying. You are all your first days of school and summer vacations and the dates you’ve had with someone you were trying to get to know. You are the sum of ALL your experiences, and you are under no obligation to share with potential partners any of the isolated experiences you feel uncomfortable with or ashamed of or that don’t effectively represent who you are now.
Since your specific question relates to how you lost your virginity and that’s something that sometimes comes up in relationships (and I do agree that some women would have a problem with the way you lost yours), I’d just come up with a vague response if you’re ever asked about the specifics of losing your virginity. Something like: “I lost it on vacation in a one-night stand and it wasn’t meaningful and I regret that part, but I also learned something about myself and how important it is that there’s emotional intimacy before enjoying physical intimacy with someone.” That isn’t a lie at all, and it highlights something of your character that would appeal to a lot of women. Clearly, you’re a sensitive, thoughtful man, and I hope you don’t let this one regret you have ruin your confidence and keep you from pursuing meaningful relationships.
Related: I’m curious as to how many people have asked or know the details of how each of their significant others lost his or her virginity. I sort of don’t think knowing these details about a partner is as common as you, LW, think it is. I’ve been with my husband for nine years and I never thought to ask how he lost his virginity, at least not that I remember (and, if I did ask or if he shared it, it must not have been very important to me since I clearly have no recollection). I know roughly how old he was, and I do know how many women he’s slept with — not because I asked but because we both volunteered our numbers once in one of those giddy conversations you have early in relationship when you’re so eager to really, really know each other — but beyond that, I just don’t care about his sexual history and I don’t think he cares about mine. After all, it has almost nothing to do with our life together (with the obvious exception of whatever experience we gained before we met and how we apply that experience to our, um, relations) and it certainly doesn’t define who we are. What about other people? Do you know how your partner lost his or her virginity? Do you care?
If you have a relationship/dating question I can help answer, you can send me your letters at email@example.com.