Image via Shutterstock
Image via Shutterstock

Hello, you love swamis of the Internet. Welcome to Ask Dr. NerdLove, the dating advice column that’s powered by Protoculture.


This week, we’ll be talking about some of the more unusual questions that can crop up in your dating life. What do you do when you’ve fallen in love with someone you shouldn’t have fallen in love with? And what do you do when the spirit is willing but the flesh stubbornly refuses to cooperate?

Occasionally life will hit you from angles you don’t expect, so it’s time to hit back. Let’s do this.

Dear Dr. NerdLove,

I am an 18-year-old homeschooled guy who has never dated anyone before. I have liked many girls I’ve known, but have always shied away from the idea of dating because they didn’t ever seem “just right.”

In the recent years, I’ve had a secret crush on a certain girl (I’ll refer to her as ‘L’). We’ve known each other since we were little grade school kids romping around on the beach and having fun, and we grew up as friends. Everything seemed nice and rosy up until middle school. That’s when L took a turn for the worse (behaviorally and morally). She called stupid the idea of waiting until marriage to have sex, something which utterly contradicts what I believe as a Christian, according to the Bible. Although I still liked L, it saddened me deeply to learn of her new viewpoints. Things hadn’t gotten much better in the years to come. She succumbed to the flirtations of other guys without restraint, going along with anything just to be given attention (all the while that I watched it all dejectedly). She’s even casually dropped a couple f-bombs when sharing with me some mildly bothersome experiences from school. Despite all these metaphorical daggers being inadvertently stabbed into my heart through the years, I’ve still had a crush on her, and somehow kept alive a faint glimmer of hope. My heart has refused to acknowledge that the way things are now is how they’ll be forevermore.

First of all, I don’t fully understand why I have a crush on someone I know has plenty of significant faults. The only explanation I have construed is the element of time— that we’ve known each other for at least a decade. And maybe that we share a lot of similar interests. Other than that, I’m clueless.

And as for the dating situation: like I said, I have never dated anyone yet. I have been cautious and vigilant in whom I’d even consider as a potential date. Any fault I’d see would be a turnoff, and I just couldn’t seem to gain any ground.

I have had an idealistic perspective on dating in general. My dream is to marry my first date; I want to make it count. I want to be able to say I have never dated anyone before I would have met my future wife. Please tell me honestly... is this a reasonable notion to hold on to? What advice would you have in regards to L? Could (or should) there ever evolve something more in our relationship, or should I keep out? I appreciate your time in reading my letter, and all your advice.

Thank you,

Drowning in Befuddlement

OK, there’s a lot to unpack here, but before we get too deep into things, Drowning, we’re gonna need to have a little talk about reasonable expectations. Because right now, you’re setting yourself up for major disappointments.


You want your first girlfriend to be your only girlfriend. OK. Cool. It’s good to want things. Let us start with the fact that this is vanishingly unlikely to happen. I can count the number of people I know who married their high-school sweethearts on the fingers of one hand with enough spares left over for the rings of every human Green Lantern. You have better odds of winning the lottery and getting a Mondo poster than you have of making this happen.

Why? Because humans have agency. Even if you’re radically committed to making this happen no matter what, there’s no way to ensure that your future theoretical girlfriend isn’t going to be the one to dump your butt. Even if you scour the earth and find someone who’s on the exact same page as you on this “first time/only time” issue—and at that point you’re basically down to whichever of the Duggar girls are still single—people change as they grow. What seems impossible to you now becomes very plausible in a year, two years, three. Hell, my whole career is based on doing things that I thought were impossible when I was your age.

But ignoring the likelihood of things, let’s look at the more practical side of why this tends to be a bad idea. Let us start with the simple matter of finding someone who’s right for you. Yes, I know you have a checklist of things you want in a potential mate. What you want and what you’re actually compatible with are often two very different things… and you will almost never find this out until you get the shit kicked out of your expectations by the hobnailed Boot of Reality. Sexual compatibility, for example, is something that destroys many relationships. If you and your future spouse aren’t compatible sexually, then you’re going to be miserable. Right now, all you have is theory and supposition about what you want and how things are going to work. But theory without testing — and no, masturbation doesn’t count for these purposes — is functionally useless.

That theory vs. experience issue will also affect who you think you’re attracted to and why. Take, for example, the trope of the Manic Pixie Dream Girl. She represents the ur-mistake guys make: expecting a partner to fix some lack they see in themselves. She’s there to Make Men Better rather than to be a person with her own wants and dreams. Almost every guy falls for this trope until they get some real dating experience under their belts and realize the things they think make an MPDG desirable would drive them crazy in short order because life isn’t a movie. The stolid, unimaginative man isn’t going to be happy when his impulsive, excitable girlfriend is constantly changing plans or making last minute decisions, after all...

Similarly, dating experience helps you learn how to recognize bad situations and weed out partners who might be toxic for you. That person whose life seems so exciting and dramatic is often also the person who depends on your having poor boundaries. That relationship that seems too good to be true? Yes, it in all likelihood is too good, but you’ll be so excited by her drama that you’ll miss the warning signs.

Then there’s the fact that relationships and relationship maintenance is a skill and one that’s developed through deliberate practice. Once you get out of the initial honeymoon stage, you’re suddenly going to be faced with the reality of trying to make your life mesh as seamlessly as possible with another person’s, and that’s going to cause you a lot of headaches over the years. Part of the benefit of having dated around means that you learn far more about keeping a relationship alive and happy, instead of trying to get it right the first time.

So no, I don’t think that trying to ensure your first girlfriend is your only girlfriend is a good idea. I think it’s unworkable at best and a recipe for misery at worst. If you want to take a swing at that… well, cool. You do you. Just realize you will be narrowing your dating pool to single digits.


But I don’t think that’s the main issue we need to deal with here. That issue is your friend and the way you talk about her.


I think it’s time for you to take a seat and brace yourself because it’s time to meet the Chair Leg of Truth. Quite frankly: you’re being a dick to someone you call a friend. You’ve got one doozie of a Madonna-Whore complex rolling around in your brain and you’re spending a lot of time getting caught up in the mote in your neighbor’s eye.

Let’s be real here: your continuing crush on L isn’t continuing “despite” her “flaws” — more on that in a second — it’s because you want to bang her. Your pain isn’t because of her, it’s because you won’t acknowledge your feelings for her conflict with your attitude towards women and sex and you’re blaming her for not conforming to your vision.


After all, L was great as long as she was your perfect virgin. Now that she’s had the temerity to grow up in ways you don’t approve of, you’re apparently comfortable doing a shitload of judging on things that you have neither the experience nor the perspective to judge. And while I’m no Biblical scholar, I seem to recall Jesus having some fairly decisive words on who gets to do the judging.

I notice, for example, that L seems to have lost all agency in her own life; she didn’t decide to date someone, maybe even sleep with them because she’s a person with a sex drive and because she may have wanted to share intimacy with someone she loved. According to you, she “succumbed to his flirtations” for “attention” as you were helpless to stop her. Which, y’know, is a lovely attitude for someone who seems a bit more pissed that his own pants-feels are going unrequited and is choosing to blame the “slut” instead.


Disagreeing with you on religion, having sex, swearing… those aren’t personality flaws. They’re things that you might not be able to handle, but they’re not “flaws”. All that’s going on here is that you’re using them as a way to justify seeing her as lesser. That slut-shaming attitude you’re carrying around, whether you realize it or not, is part of what leads to a lot of pain and misery in the world; after all, she brought it on herself. She’s a slut. She’s trash. She’s immoral. But hey: let he with two free hands cast the first stone.

You want to deal with your feelings for L? Then it’s time to accept the truth: you want her. You may not like that you want her, but that’s your problem, not hers. She had sex. Get over it. She doesn’t agree with you on religion. Get over it.


You want to call her your friend? Then get over her supposed “flaws” and start being able to accept her as a person.


You want to have better odds of finding someone who might be willing to date you in the first place, never mind marry you, and make that relationship work? Then you need to remember that Jesus’ best friends were lepers, tax collectors and prostitutes. The vulgar, the crude, the apostates and the sexually “immoral.” The point of Christianity isn’t “ha ha, you’re a sinner and I’m better than you,” it’s to love others as they are, without reservation and without judgement.

Until then? Jerk off and wait for things to fade. And if you can’t stop obsessing about her “flaws,” put some distance between the two of you. She needs a better friend than you’re capable of being.

Hi Dr. NerdLove.

First of all. How are you? Thank you for taking your time reading so many letters and answering questions from fellow Kotaku readers.

Now, let´s get down to business. You may call me Mr.E, and I am back in the dating scene after 8 years of a monogamous relationship; my problem is pretty straightforward. I cannot reach climax with the women I have been meeting.

That is really my problem, and I was wondering if it could be psychological or physiological. I have been feeling comfortable with the few partners I have met, and I am betting it has been a two way street so far... Or at least it seems until, after a long time having sex, I get tired and call it quits.

It is frustrating for me, and I am pretty sure my partners feel inadequate when I cannot reach orgasm. I know you may not be the solution to my problem, but I know you can guide me in the right direction.

Sincerely yours.


You don’t mention whether you’re unable to orgasm when you’re by yourself, Mr. E; if you aren’t, that would go a long way to suggesting that you have a physical issue. So, keeping in mind that Dr. NerdLove is not actually a doctor, let’s break this down a little.


There’re a number of possibilities that could be affecting your orgasm. One possibility is that while you may be comfortable with your partners, you may not be attracted to them. If you’re dating people you think you should be into but aren’t, that could cause issues.

You might also not be having the kind of sex you need to have to get off. The conflict between the sex you’re having and the sex you want can often mean that your arousal pattern never reaches that peak because there’s that one critical factor missing.


You might be feeling guilty or believing that you don’t deserve to be happy or enjoy sex with someone — especially after getting out of a long-term relationship.

There’s also the possibility that there’s a medication issue. A number of antidepressants like Zoloft have side effects that make it so that you can’t cum for love nor money.


But if you’re able to orgasm on your own, but not with a partner, then the most likely issue is in how you’re masturbating. Guys have a tendency to jerk off in ways creates stimulation, friction and tightness that the human body simply can’t match. You may be squeezing tighter than any human orifice possibly can. You may be using a technique that generates far more friction. The problem with this is that, if you get used to that particular masturbatory style, you’ll have basically carved a groove in your brain; now you’ll need that specific stimulation in order to get off and you can’t get it through partnered intercourse.


So what do you do?

Basically: you take your penis off the table. Er, as it were. You have to break not just the habit of how you’ve been masturbating but also the texture, routine and patterns your cock has gotten habituated to. You, for all intents and purposes, are going to starve your penis of sensation. This means no masturbating, no blow-jobs, no penetration. Your dick is just for pissing and decoration for the next month.


This doesn’t mean that you’re going to go without sex, mind you. Make out with your partners. Go down on them like you’re drowning and they’ve hidden a scuba tank between their legs. But your penis stays out of it. You don’t touch it. They don’t touch it. You are just going to leave it alone until basically it becomes so starved for stimulation that anything will set it off. And that is when your date is going to be the one to get you off.

Following that successful orgasm, you’ll need to change your masturbation habits. You’ll want to vary things up to keep from getting habituated again. Use a light touch sometimes and a stronger one others. Lots of lube, minimal lube, slower and softer, fast and furious, etc. You might want to consider getting a toy like a Tenga Fliphole or a Fleshlight: something that will give you sensation akin to the human body instead of something that bodies could never meet. Just be careful not to let yourself get stuck in a pattern again.


And if the issue is in your head? Then it may be a good idea to talk to a sex-positive therapist and work with them towards finding a solution. The American Association of Sexuality Educators, Counselors and Therapists has a referral page to help you find someone in your area.

Good luck.

Were you a virgin until marriage? Have you had difficulty with performing in the sack? 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.


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