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Ask Dr. NerdLove: Should I Tell My Girlfriend I Lost My Virginity To A Sex Worker?

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Greetings, you corrupting porn tentacles, and welcome to Ask Dr. NerdLove, the first dating advice column to compete in the Kumite. This week we’re talking about sex, sexual shame and the intense emotions that run rampant when we start getting busy.

How important is it to disclose your entire sexual history? Is an infidelity in the early days an automatic relationship killer? It’s time to gird your loins and insert coins. Let’s do this.

Hello Dr. NerdLove,

Let me start by saying that English is not my native tongue. I apologize in advance if my grammar sucks, but I hope it is sufficient to convey my issue / question.

First, I need to give a little background: I am 32 years old. 5 years ago, I was diagnosed with testicular cancer. Usually that’s the kind of cancer that has a survival rate of over 90%, if it’s caught early. The doctors told me I was one of the unlucky 10%. My cancer eventually progressed to stage 4 and spread to my spine and my lungs. It took intensive medical treatment (chemo, lots of surgery) over a period of 3 years to keep me from dying, but it worked. I survived.

I had survived, was 30 years old and...a virgin. I don’t want to go into the details of why I was still a virgin at the age of 30, because they are not really important to my question, although I would like to say that I am not bad looking. I am about 1,80m and weigh 80 Kilos, have blonde hair and blue eyes on which girls have complemented me in the past.

Lying in the hospital, one of the things I regretted the most was never having experienced sex or having a serious relationship with a girl at all. I swore to myself that if I got out of there alive, I would try to fix that. Therefore, when I got out, I started with the sex part, because I thought it would be better to get some experience before jumping into anything like a relationship. Since I did not have a lot of experience with girls and, to be frank, thought that my numerous surgery scars were ugly, I didn’t think any girl would want me. Therefore, I decided to go to a professional, which is legal in my country. I got a few thousand Euros from my insurance company (doesn’t really matter why) and decided I would spend half of it for fun things and save up the other half responsibly. The fun thing, I decided, would be hookers.

I went online, quickly found the desired address, manned up and drove there. I was very nervous the first time and honestly, the sex was not very good. However, I liked it and decided to come back, to get some experience. I had sex with many different women and thought I was getting the hang of it…until I met her. Let’s call her Bella. Bella was 8 years younger and we hit it off right away. The sex was so much better than with all the other women and at first, I didn’t really know why. Until I realized I was beginning to fall for her. Luckily for me, she was falling for me, too. One thing led to another and we went on our first real date and became a couple after that. The relationship lasted about 6 months. At first, I thought I would be ok with her being a sex worker. However, after a while, it became clear I was not. The thought of her being with another man made me sick. To make matters worse she constantly lied to me, stood me up, didn’t answer calls or whatsapp messages for days on end…let’s just say it was a really shitty relationship. I was inexperienced and I kept it going long after I knew it was over. We didn’t end it on good terms and had a really huge fight. We have not spoken since and I believe that’s a good thing. I do not want to see her ever again.

Fast forward to today. I am in a very happy relationship with a 29y old gorgeous looking, intelligent woman. We met a year ago and took it slow at first. After 2 months, we became a couple. We really clicked on many levels. Intellectually, emotionally and physically we are a very good match. We can talk for hours on end, love spending time with each other, have amazing sex and just can’t get enough of each other. I have met her folks and she has met mine. She likes my folks and I like hers. We want to move in together soon. We tell each other everything and I am as honest with her as I have never been with any person in my life. I love her. She loves me. She is the most important thing in my life and the girl I always hoped to meet someday. I am the luckiest person in the world right now.

So, to finally get to the question: I want to be as honest with her as possible, but I haven’t told her about my relationship with a sex worker or that I have been to a sex worker (many, in fact – always safe sex of course) at all. She is a little conservative and I don’t know if she would take it too well if she knew. I think it might change her view of me. Maybe she would be disgusted. Many women I know don’t think too kindly of men who visit prostitutes. I want her to know everything about me but at the same time, I don’t want her to be disgusted with what I did. To make matters worse, I told her a false story about the loss of my virginity, because I was ashamed. I lied to her. I am afraid she will be angry at me for lying to her about something so intimate.

Should I tell her or is ignorance bliss?

House of the Rising Sun

You sound like you’ve got a lot of shame built up around this issue, HORS. First you were ashamed of being a virgin, now you’re ashamed of how you lost your virginity. That, more than anything else, is your biggest problem.


I mean, come on dude, you beat cancer. You stared Death in the face and Death blinked. That should rank higher in your self-conception than who you dated or how you lost your virginity.

But I get it. Your sexual history goes against all the tropes and stories about How Men Are Supposed to Be. You’re a virgin later in life! Boo! You paid to lose your virginity! Ick! How unmanly! Clearly you couldn’t get it any other way!

Here’s the thing: all that is bullshit. We treat being an older virgin - especially male older virgins - as though it says anything about that person other than “they haven’t had sex yet”. We have a cultural narrative about manhood and sexuality that’s invented out of whole cloth and promoted through pop-culture: that your first time needs to Mean Something, that you have to lose it by a certain age (ideally high-school, by university at the latest) and in a certain way because it goes on to define you. It should be an event, because it’s the final milestone between you and being a Real Man.


Paying for it is somehow cheating the system because it doesn’t become part of the referendum on you as a man. You’re not earning that sex through having game or being someone worth fucking, so clearly you’re a loser who couldn’t hack it.

The truth is, who we have sex with and why has little to nothing to do with “deserving” or “earning it”. Men and women choose their sex partners for an almost infinite number of reasons, many of which have absolutely nothing to do with the other person in the first place. People choose to have sex because they’re bored, because they’re feeling ugly and want to be validated, because they’re angry at someone and want to make a point, because they want to feel something or feel like it’s something they should do by now.


Yet somehow it’s so much more shameful to go to a professional for your first time than it is to get drunk and have a fumbling, half-remembered and unsatisfactory hook-up with someone who just wants the nearest warm body that doesn’t actively repulse them.

The fact of the matter is: how you lost your virginity doesn’t really say anything about you as long as everyone was safe and consenting. Honestly, as long as you were a decent client - you were polite and considerate of the sex-worker’s feelings and safety, tipped well, etc. - and everyone involved was on board with the transaction (including her wanting to do sex-work, not being coerced into it), then it’s no harm, no foul. You had an itch, you got it scratched in a quick and efficient manner. It may not have been one that everyone would choose but that’s their damage, not yours.


I suspect you may have some lingering shame about having dated Bella as well; after all, how could you possibly fall for an escort? How naive and absurd could you be? But as someone who has a number of friends who do sex-work of varying forms… sex workers are people. Some are assholes, some are saints and most are somewhere in between. They date, they have relationships, they have lives and hobbies that lie completely outside of their jobs. Some people don’t approve of what they do for a living, but then again, folks didn’t approve of actors, doctors and bankers at one point or another.

The best thing I think you can do is accept that you didn’t do anything shameful. You had some learning experiences, including learning that you can’t do non-monogamous relationships and that you aren’t happy dating an asshole just because the sex is good. Those experiences made you who you are today. And it sounds to me like—that bullshit shame aside—you’re pretty darn happy with you who and where you are.


So that brings us to how to talk about this with your girlfriend and whether you should tell her about Bella and the others. I’m of two minds.

The first mind says that relationships aren’t depositions. Being in a relationship doesn’t mean that you have absolutely no secrets, nor does being honest with someone mean blabbing everything off the top of your head with no filter like you’re Jim Carrey in Liar Liar. If there’s no real need for your girlfriend to know that you’ve seen a sex-worker, then you can elide over the financial aspect of things with a clear conscience, if that’s what you want.


Creating a fiction out of whole cloth, on the other hand, is less acceptable. To be fair: lying about how you lost your virginity isn’t that big of a deal; it’s not like you’re admitting you’re secretly running a meth empire. However, it’s still a bad idea in general. If you feel the need to come clean, then I’d advise being honest about why you lied: you feel a little embarrassed and ashamed about how you lost your virginity and felt a little insecure in your relationship those early days, so you made something up instead.

The thing you should keep in mind is that most people have a mental image of both sex workers and their clients that has no relationship to reality. They know the Hollywood version or the Morality Play version, but not actual people. Your girlfriend knows you’re a sweet and loving guy who she’s lucky to be in a relationship with. Knowing that you also visited sex workers back in the day and you’re not a creep or a loser might actually cause your honeybunny to rethink her attitude towards the whole enterprise.


Or it might not and the whole thing might fall apart.

I won’t lie: it’s a risk. But here’s my question for you: while I don’t think there’s really a problem with leaving out some details that would cause needless conflict, do you want to date your girlfriend if she can’t accept you for who you are? If your values are different enough that these minor issues in your past would disgust her and make her leave… well, would it not be better to discover this incompatibility early, instead of having a ticking time-bomb waiting to go off in your relationship?


I can’t answer that question for you; only you can.

Regardless: I don’t think you need to share every little detail about your sexual history, especially if it’s not immediately relevant. There’re some things she has a right not to know, and you’re not obligated to tell her. If you feel that telling her about Bella and the others would cause unnecessary strife, then go ahead and stuff it down the memory hole.


Good luck.

Dear Dr. NerdLove,

English isn’t my first language so I apologize for any mistakes.

I’m a young man that currently is studying at university. I’ve always have found it difficult to start a relationship with someone, since I’m the type of person that doesn’t like to open up my feelings out of fear of getting hurt. It has always been easier to only have friends with benefits and one nights stands to avoid that (it must be said that since I’m very good looking and easy-going, satisfying my sexual needs have never been a problem).

My problem began when, a couple weeks ago, I met a very special girl. She reached out to me before I did (and wanted to), and we started talking. The day we met in person, we were with a group of mutual friends drinking a few beers outside of my university. She was incredibly funny and to hear her talk filled me with passion. When the bar closed, a friend invited all of us to his house, and I went there with her. On the way to my friend’s house, we finally kissed. Just as we arrived, I left because I was feeling very tired. But I couldn’t take this girl off my mind.

We started dating and it was perfect. Last week, we had a university trip to Costa Rica, and both of us went. It was absolutely beautiful. We went on long walks together, night clubs, swam at the beach, laughed together, and finally we had sex (I’d like to point out it was incredibly good).

But the last night there, she came up with me and told me that, before the trip (the day we met after our first kiss, and the couple weeks we were dating), she was having sex with my friend (the one that invited us to his house).

I felt heartbroken and gutted. Our perfect time together in Costa Rica now had a stain of what happened before. I felt vulnerable because I was opening myself to this girl and then I found about this. She apologized, and told me and my friends that she wanted to be with me, that she was really falling for me. But I couldn’t stop thinking that if my friend had come on the trip, maybe we wouldn’t have had this amazing time together.

I sometimes idealize moments, and that happened with our first kiss. To think that she was with my friend after that didn’t feel good. One thing that I have always avoided in my relationships is to feel like I’m in a competition. My last girlfriend always made me feel that way and I ended up with low self-esteem (reading you was an important motivation to end that toxic relationship).

Now we have returned from the trip and I don’t know what to do or what will happen. I told her how I felt and that I needed time. I miss our time together from the trip but I don’t know if it was real or not.


Troubled Guy

OK, there are going to be two parts to this response. The first is the cold truth that she wasn’t cheating on you when she was sleeping with your buddy. You and your snugglebunny hadn’t had the defining the relationship talk and didn’t have any real expectation of exclusivity when she hooked up with your friend. Your timeline’s a little blurred, but it sounds to me like you weren’t even dating when this happened


So, honestly, the biggest problem is that you kinda sound like you got a bit over-invested with her before you really should have.

I want you to remember something important: dating isn’t a competition. People don’t pick their partners by compiling a list or setting two people against each other to prove who’s more worthy. You’re not competing with anyone. Dating, at its core, is very simple: does she like you and want to date you? It’s not “do you have more Man Points than the next closest contender?”


Similarly, her hook-up with your buddy, whether it was an infidelity or just the actions of someone who wasn’t exclusive yet, doesn’t affect the reality of what you two had together in Costa Rica.

Sex and sexuality are complicated and people are even more so. Love doesn’t mean you don’t desire other people. Desiring other people doesn’t mean you don’t love someone. You can love one person and lust for—even fuck—someone else without it saying anything about your feelings for your partner.


For the purposes of this column, let’s take you at your word and treat this as though she had cheated on you. If you want, you could just leave her. She hurt you, after all. But before you make up your mind, I want you to consider that not all infidelities are equal.

Some infidelities are affairs of circumstance, where the stars aligned in just such a way that a lapse in judgement could happen. Usually, the cheating partner realizes they fucked up, they feel horrible about it and wish it had never happened. In cases like these, the odds are high that the cheating partner won’t make the same mistake again.


Other times, it’s a case of someone not giving a shit about whether they hurt the person they supposedly love. Or perhaps they’re slamming their hand down on the Relationship Self-Destruct button. Or they may just see commitment as an inconvenience to be ignored when needed.

It sounds like your girlfriend—again, even in this hypothetical situation—is in the former category, rather than the latter. She wants to be with you, exclusively. So, the question becomes: where do you want to go from here?


Are you willing to forgive all this and take her at her word that it’s in the past? More importantly, are you able to do so? If you take her back, are you able to move past this and not hold it over her for the rest of your time together?

If you do decide to move forward, what is it going to take to fix things? Is she going to be able to prove to you or help you see that she does care about you? Or will her infidelity—and the toxic abuse of your ex—keep lingering over everything like a fart in church?


You were both relative strangers to one another when this happened. You were dating (for suitably low values of dating) for less than a couple of weeks. You barely knew one another. You know each other better now, and that knowledge informs your relationship and why she’s chosen you.

It may be better to treat your initial time together as a false start, a prologue that introduces the characters and sets the stage for the real adventure. You’ve had your set-up. Now your real relationship can begin.


Good luck.

Hey Doc,

I was the guy who submitted this question - Help, I’ve fallen in love with a Cam Girl.

I just wanted to give you an update of sorts.

First things first, yes, I did thoroughly read your response dozens of times. I was so eager to see if my question was worth your attention that I almost followed up to see if you got it. Your post on Kotaku, of course, confirmed that you did, and I just want to let you know that I appreciate you so much for world-class communication and professionalism.

So here’s what happened with Camgirl:

When I saw it for what it was, instead of confronting her I asked how she would feel about hanging out in person at any point in time, even years from now. I didn’t do this to actually accomplish it, but to see the response. And, sure enough, just like you said, her response was “You’re so sweet, you’re so cute, you’re such a good friend/person” etc until, in about 250 words, said “no”.

The most surprising thing wasn’t her response, though. It was my reaction.


Holy shit, it didn’t hurt. Holy shit, I’m not sad anymore. Holy shit, I’m not gonna cry myself to sleep over whether or not she would say “yes” to anything that I want but she clearly does not want. Because...perspective? You told me exactly how she was going to respond, and she did just that. I knew it was coming thanks to you. So, first of all, I appreciate that.

If you think I’m just bullshitting you with praise, let me give you a dollar value of that lesson: $10,000.

That number represents approximately how much I spent on strippers, strip clubs and cam girls in the year before I saw your Kotaku post. Had I not asked you that question - had I not been brave enough to just face myself, be honest with my feelings, and ask someone for help, I probably would have spent another $10,000 on more strippers and cam girls.

Upon reading dozens of your articles on your site and Kotaku, I’ve come to terms with a lot of shit I did in the past that I was a little too comfortable sweeping under the rug. You helped me realize that it doesn’t matter that I’ve been in seventeen relationships, because I don’t even know how women work (or how relationships work for that matter). I kept doing the same thing and expecting different results, like a fucking idiot.

I spent that next $10K on actually giving a shit about my health. I bought an $800 bed so I can sleep properly and not fuck my back up by 29. I bought several game consoles, because gaming is a hobby I’ve had since I’ve been a child (speaking of which, not a single one of the seventeen women I dated was a gamer, because I clearly wasn’t looking for someone I have things in common with). I buy healthy food and cook for myself now, so that I can be awake longer and feel better. Also, it turns out that women like when you cook, because apparently food is a thing that people like and consistently need.

If I actually want to attract women, maybe I need to give a shit about my body, my personality, my home, my soul, and other things that make me who I am.

You saved me $10,000 with 2,000 words. For that, I honestly could never pay you back, no matter how many views I give you or how many of your books I buy.

Thank you, Harris.

Not In Love With the Cam Girl Now

Glad to hear you’re doing so much better, man! Hope you keep up all the progress you’re making!


Did you lie to your partner about a significant part of your life? Did your relationship survive an infidelity? Share your thoughts and experiences in the comments, and we’ll be back in two weeks with more of your dating questions.


Ask Dr. Nerdlove is Kotaku’s bi-weekly dating column, hosted by the one and only Harris O’Malley, AKA Dr. NerdLove. Got a question you’d like answered? Write and put “Kotaku” in the subject line.


Harris O’Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove podcast. His new dating guide New Game+: The Geek’s Guide to Love, Sex and Dating is out now from Amazon, iTunes and everywhere fine books are sold He is also a regular guest at One Of Us.

He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.