Ask Dr. NerdLove: She’s More Sexually Experienced And It’s Freaking Me Out

Image via Shutterstock.
Image via Shutterstock.

Hello all you galloping Sex Weasels, and welcome to Ask Dr. NerdLove, the only dating advice column with the Super FX chip AND blast processing.


This week it’s all about sex… more specifically, folks who haven’t had it and folks who haven’t had as much as others have. How does an older virgin make up for lost time? Is he always going to be at a disadvantage compared to people who bloomed earlier? And what if your partner’s had way more sex than you? Does that change the balance of the relationship?

It’s time to calm some fears and bust some myths. Strap in folks, we’re gonna do this thing.

Hey Dr NerdLove!

So, long story short here; I’m a 28 dude, and after never having ever been on a date, had a first kiss, been intimate, yadda yadda, and years of nothing going for me on places like OkCupid and Tinder, over the last 12-13 months, I’ve stumbled my way into 3 relationships. Unfortunately, they all ended for, as far as I can tell, the same reason, and I’m not sure how to approach it.

The first girl I was seeing was going well, I was at her house one night, we were playing truth or dare, and of course she asked if I was a virgin. When I said yes, she literally called off everything on the spot and told me it was for that reason (she said virgins are clingy, I dunno). The 2nd girl I saw was cuddling with me in bed one night when she asked me how many women I slept with; when I said 0, she... basically called off everything on the spot. The third girl I saw was going particularly well, we had spent a lot of time together and really, really hit it off well, and both had said how much we liked each other a lot. The subject of my sex history never came up, but suffice to say, when things got hot and heavy at my place, my performance anxiety was so bad (I was physically shaking) that it didn’t really pan out. She broke up with me via text about 72 hours later.

Now, like I said, I’m 28, and I totally respect and understand that people my age are probably not exactly keen on going through with someone who is new to just about everything, from the social aspects of a long term relationship to the sexual ones, but... I don’t know how to play this. Is my lack of experience something I am totally open and upfront with right away, and I hope they accept it, or will that just scare people off? On the flipside, is being coy and guarded going to just make for a messy situation like girl 3 that nobody wants? Obviously, dishonesty isn’t an option, but I have no idea how I communicate (or not) my lack of experience.

The reality is I have horrible anxiety and it runs in the family. I’m seeing help but having a healthy sexual relationship with someone is probably going to take multiple tries and effort on both our parts before I am comfortable. And between that and the lack of familiarity on my part, I can see someone bailing if it comes up. But I also know I can only hide the subject for so long until it rears its head in bed.

I guess I need to know how to approach this: wear it all on my sleeve right away, or let the chips fall where they fall and hope for the best? I wish I could just spill out everything and have someone be totally understanding and we try to work through it. I will do my best to self-improve, but at the end of the day, 3 people who I all thought were pretty swell effectively dumped me either over my lack of previous experience or lack of ability. And until I actually get over the hill, both sexually and in terms of being with someone for more than 3-4 months, this is going to bother me more and more and make it even harder for me to maintain any confidence or optimism. All I want is a fair shake and an honest shot at getting better and making it work. I know it might take time and effort but I am willing to work hard on it. I just don’t know how I should communicate this with someone and handle the situation.

Thank you!

First Time Not Lucky

There’s a saying that I was taught at Fake Internet Doctor med school, FTNL: Once is happenstance, twice is coincidence, three times is enemy action a message. But the key is making sure that you’re getting the right message.

And in your case, I think your problem is that you’re mistaking side-issues (your virginity) for the real issue: your anxiety. Let’s break things down how this all works, shall we?

It’s a little weird in that three women in a row asked you about your sexual history or lack thereof. While this can come up in casual conversation, it’s usually something that comes up after you’ve slept together. More often than not it’s the “tell me a bit more about yourself” style of conversation, not “you must be X level to enter the raid” kind of prequalifications.


Now despite what a lot of dudes claim, straight women can’t smell virginity on somebody. What they can tell — hell, what lots of people can tell — is when you’re having a freak-out and trying to hide it. Considering that your third encounter involved being so worked up that you were actually shaking… well, I suspect that your nerves were coming through so loud and clear that they could be seen from a mile away. That, I suspect, is what prompted the questions.

Needless to say, talking someone down from something approaching a full-bore panic attack when you’ve only been on a date or two (or three) is something that most people aren’t going to be into, so I’m not entirely surprised that was the end of the dates.


So here you are: three bad results and quite understandably shaken by this. And to be fair: your dates were… less than diplomatic in handling an unexpected situation. (Well, and the “virgins are too clingy” one was unnecessarily asshole-ish, and spreading a bullshit myth besides.) So the question becomes: what do you do about this?

Well, you’re already doing the first thing I’d suggest: seeing a therapist and getting help. The more you can get your anxiety under control, the better you’ll be doing in general on your dates. Medication may well help you deal with the anxiety. Hell, if it’s available in your area, weed may be helpful too; a low-dose edible might take the edge off enough for you to relax and just be in the moment without impairing you.


But like the Buddhist monk found out after paying for a $4 hotdog with a twenty, true change must come from within. In your case, that means that you have to start changing how you look at your virginity.

The truth is: virginity is fundamentally meaningless. It says absolutely nothing about your worth or value as a person. The Standard Virginity Narrative tells us that guys are supposed to lose their virginity as early as possible — preferably in high-school, if not sooner — but that narrative is bullshit. It’s made up. It’s part and parcel of toxic, bullshit ideas surrounding what makes someone a “real’ man and teaches us to ignore cases where boys were sexually abused or raped because they got “lucky” with an older woman.


Being a virgin doesn’t mean that you’re defective as a man, nor that there’s a “reason” why women haven’t chosen to sleep with you. Women decide to sleep with someone for a multitude of reasons. Sometimes it’s because they want that person in particular, other times it’s a case of “well, it’s Friday, I’m feeling horny and you’re the least objectionable option out there so you’ll do”.

(And, I might point out, you were on the verge of getting laid three times until your anxiety pulled the ripcord. So you’re clearly someone women want to sleep with.)


At its core, all being a virgin means is that there’s an experience you haven’t had yet. That’s it. Once you’ve done the deed, you are going to be the same person you were beforehand. You will look the same, you will act the same, you will have the same personality. The only difference is that you will have done something new. Everything beyond that is value that you put on it. And you, clearly, are putting so much importance on it that you’re throwing yourself into a spiral of panic.

This is why you need to recognize your virginity for what it is: just a data point about you. It’s value-neutral, akin to hair color or handedness. Some people may value it highly; some may find it irrelevant. But that’s on them, not you. You. Are. Fine.


So here’s my suggestion for you: dial your shit back, especially while you’re working on your anxiety issues. Rushing to punch your v-card is not going to solve your problem. All it’s going to do is make your first time into an even bigger Life Event with capital letters and that will make you even more anxious.

Don’t get me wrong: this doesn’t mean don’t date. What I am suggesting is that you want to take things slowly. You want a partner who’s going to be caring and compassionate and not rush things, which will give you more time to sort out who’s on the same page as you. A partner who respects that you may need to take time to get comfortable is going to be someone who’ll be more patient and giving when the moment does come.


Now, as for whether you should bring it up… I’d say that’s up to you and how you feel. It’s not something that I think is that important to bring up immediately, or even necessary. If the question comes up and you want to dodge it, something like “less than some, more than others” or “Enough to know what I want,” works well.

If you do want to be up front, then pay attention to how you talk about it. People in general will take their lead from you. If you treat your virginity as a mark of shame, something dark secret you’re only revealing under duress, they are going to treat it that way. If it’s just something that you’re matter-of-fact about, that it’s no big deal, then they’re going to follow your lead too. Why are you still a virgin? You were prioritizing getting your life in order, you didn’t have much time to date when you were younger, you never met the right person… these are all perfectly legit reasons. But the underlying message is the same: it’s not a big deal. You’re not embarrassed by it. You’re not ashamed about it. It’s just a thing.


And if they do have a problem with it? Well… you’ve told them one thing about you. But they’ve told you everything about them.

So, TL;DR version: get your anxiety under control, take things slow and make sure you’re dating the right people. Someone who gives you shit for being a virgin is showing you that they’re a judgemental asshole and are best tossed out of your dating pool at the earliest opportunity.


You’ve got this, FTNL. Good luck.

Dr. NerdLove,

Hey, I love your column and never miss one. You give great advice and also excel at just making everything interesting, regardless of subject matter.

I’m in a good position right now, in a newish relationship with a woman who was my coworker and friend for a year before we started dating. Since then, things have been great and we both feel this has the potential to be a permanent relationship.

The issue we have is entirely an internal one on my end. My girlfriend and I are fairly different in age – I’m in my thirties and she’s twelve years older. That alone isn’t a problem. Since I was 18, I’ve had a thing for older women (though I mainly date people closer to my own age). She is beautiful, feisty, and treats me better than anyone before her. Voracious, too.

What makes me a little uncomfortable at times is the greater number of partners she has had. Yes, of course someone older has had that much more time as a sexually active adult. And there was a period of marriage in there that took her out of the game. But most of my hookups have been as part of relationships, with fewer than ten one-time-only experiences (and most of the time, I’d have been up for seeing them again).

In comparison, my partner seems to have engaged in a lot more casual sex. Going home with guys at bars, hooking up with someone to feel better after a breakup or other unhappy life event, etc. When we talked about how many partners she had during the pre-relationship time we knew each other, she guessed five but only remembered three specific people. That uncertainty, it bugs me.

I know there’s nothing wrong with a woman or man sleeping with as many people as they want. I don’t criticize or think less of her for it. But at the same time, some dumb part of me is bothered by the disparity, that she is so much more casual about sex than I am. She says I make her very happy in and outside of bed and I know she’s not going to cheat on me. But that ugly voice still whispers in my ear now and then.

Do you have any advice for overcoming these jealous and uncomfortable feelings about my partner’s past? I want to be the best guy I can be for this fantastic woman, and get my highly anxious mind more relaxed and focused on the present and future.

Not Quite as Experienced

My dude, I am going to give you the only advice you need here: let it go. You have an awesome relationship with an awesome woman. Clinging to this idea that casual sex from her past has anything to do with you and the sex that the two of you are currently having is going to be the poison that ruins things.


One of the biggest mistakes that you — or anyone, really — can make is assuming that the number of partners a person has had means anything more significant than “this is the number of people I’ve slept with.” The reason why someone may have more or fewer partners than somebody else is so varied that it’s impossible to draw any meaningful correlation that doesn’t start with bullshit ideas about sexuality.

Some people take sex incredibly seriously and only within specific relationships. Others see sex as no big deal. Some people have lots of love to give and see sex as being a natural expression of that love — for friends as well as romantic partners. Some people fear sex. Others use sex for validation. Some even use sex as a weapon, either against others or against themselves.


Some people happily have what they will call their “slut interval” where they’ll fuck around while single but are also happily monogamous when they’re committed to someone. Others think they should be monogamous but aren’t capable of it. And others are only capable of sexual attraction to someone that they have a strong emotional connection to.

All of which is a long way of saying: numbers are basically bullshit. People matter. The connection you have matters.


That’s what you need to pay attention to: the connection you have with your girlfriend. She may have had casual lovers before, but she has chosen you. She cares about you and (presumably you have discussed this) has agreed to be exclusive with you because you know what, you’re worth it.

Now here’s the thing: you don’t want to make the mistake of trying to force your jealousy away. You feel how you feel and trying to make yourself not feel it or pretend you don’t is like tying a knot in a hose. It stops the flow but the pressure is just going to build until things explode. It’s better to turn off the source than it is to try not to feel.


Part of that is just tackling the why rather than the what. It’s not just that you feel jealous but what, specifically, bothers you. In this case, it’s the feeling that she doesn’t take sex seriously, which means she doesn’t take her relationship with you seriously.


Now maybe it’s simply a values difference; you’re one of those people who treats sex as SRS BZNESS and preferably part of a relationship. Maybe it’s a little unpleasant Madonna/whore complex that you haven’t been able to fully root out. But it’s worth digging in and exploring the root causes and labeling them. Because once you do, you’ll be able to actually start sorting things out.

If it is a case of, “Well, if she’s casual about sex, is she casual about her affections?” then look at how she treats you. Learn her “love language” if you will, the way that she expresses her feelings for you. It may not be through sex but through other ways.


If it’s that her having had more partners means she’s going to be pickier or that you won’t measure up… that ain’t how it works. People don’t date on an upward graph. People don’t only date someone if their current partner is the new Best They Ever Had. Sexual satisfaction is important for a relationship, but it’s a part of the relationship not the sum totality of it.

If it’s that her having had more partners means that sex is devalued or that she’s devalued… well shit, the only thing I can say is, build a bridge and get the fuck over it. Learn to realize that she’s more than the number of people she’s seen naked.


Now, this doesn’t mean that recalibrating and shutting up the voice of your jerk-brain is easy. It takes conscious effort to tell that voice to sit its two-buck ass down before you decide to make a change. And part of what can help is talking to your girlfriend and saying, “Hey, I’m having a stupid jealous moment, could you help me talk it down a little?” That doesn’t mean that she gets to do all the emotional heavy lifting — that’s on you. But being willing to open up to her, tell her that this is what you’re going through right now, and ask for some occasional reassurance? That’s a big part of what makes relationships work.

But more than anything else? Trust her. Let yourself believe her when she tells you how happy she is. Recognize that everything in her past has led her to where she is now and made her the person that you care for. And whether you are necessarily cool with it or not, her past is important, because it’s what’s made possible the awesome future you two are going to have together.


You got this. Good luck.

Did you lose your virginity at an older age? Have you dated someone with a significant age/experience difference? Share your thoughts and experiences in the comments. And meanwhile, we’ll be back with more of your questions in two weeks.


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? and put “Kotaku” in the subject line


Harris O’Malley is a writer and dating coach who provides geek dating advice at his blogPaging 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.


sailor shitpost

The second guy thinks five partners is a concerning amount of sexual history...?? Buddy... that’s not even the least bit unreasonable.

When the letter started and he mentioned the woman’s age and how she likes going home with men at bars, I was prepared to imagine like... 20 sexual partners. But five??? You could go through that number of sexual partners in a few years of dating, dude. Especially if you have a flexible definition of what counts as a sexual partner and what doesn’t.

And of course the fact that she’s older is another huge factor here. This isn’t a twenty year old with five sexual partners, but a grown woman who’s dated, been married, been divorced, and then started dating again.

Respectfully, I think this may be a bit of that good ol’ subconsciously-operating, society-imposed sexism controlling your thoughts here. The Doctor alluded to this in his response to you but he didn’t flat out say it, probably because it’s admittedly probably not the only factor. It doesn’t meant you’re a misogynist, it’s just a result of living in the society we live in, with its double standards and puritanical attitudes and everything. But it really is something you’ve got to let go, because it’s not like you can go back in time and change it. Thinking less of a good woman over something like this is just silly.