Hello, Internet! Welcome to Ask Dr. NerdLove, the only dating column to stare down the eye of the storm and make it blink.

This week, we have two young lovers in the midst of a tangled web of troubles. One reader has ended up in a complicated relationship with his best friend’s sister and isn’t sure how to extricate himself without causing any more drama. Meanwhile another reader and his girlfriend are having a hard time crossing the finishing line, if you know what I mean and I think you do…

(Orgasms people. We’re talking about orgasms).

Let’s do this thing… and when the flood waters rise and the tornadoes fall from the sky and the pillars of heaven shake, remember what ol’ Doc NerdLove does: he looks that storm square in the eye and says, “Go for it, I’ve got homeowner’s insurance.”

Hey Doc.

A few years ago, I made a new close friend. Whenever I went to his house, I saw his sister, who was cute, but had a bit of a bitchy attitude. Still, she wasn’t interested in me which didn’t bother me at all, since I wasn’t interested in her.

Over time, we started talking, including some serious talks about how she acts towards people and built up a level of trust. We even ended up sharing sex jokes every now and then; she didn’t even see me as a potential partner, and I didn’t see her in any other way than my friend’s sister who is rather cute.

A few weeks ago though, those sex jokes quickly evolved into outright sexting, and I’ve come to realize that apparently she wants something serious, while I don’t. I feel a little awkward about this: I didn’t hear her out and try to help her just to try to fuck her later; I never tried to hit on her, I just wanted her to be better emotionally speaking. Of course, sexting and (if this goes on) sex is just a bonus, but I’m feeling a bit guilty about it now. She kind of got infatuated, and right now I don’t know what to do.

She’s my best friend’s sister (who is, I repeat, cute), I’d hate myself having to distance him because of it, or causing her problems in the long run. I never really tried to get into her pants while trying to help her (and I’ve mentioned this over and over), but at the same time, I guess my will just wasn’t strong enough about saying “no” and now she’s pushing for sex and/or constant sexting, and of course, my hormones won’t say no to that (nor the pictures she sends).

Her current behaviour (whether it’s in sexting or just daily messaging on her end) screams she’s into me, and not just sex. Maybe if it were just the latter, I would probably go ahead, but as it stands, I can only see trouble brewing if this keeps going. Talking to her about the situation seems to lead to crying on her end (not about the situation, but her low self-esteem -see bitchy attitude mentioned earlier-), and so I’m concerned about hurting her.

Sorry if I rambled too much, just hoping you can help me clear up on this matter the best way possible.

Trying To Not Be a Dick.

Your words are saying one thing, but your actions are saying another, TTNBAD. It’s a little hard to take your claims of not wanting to bang your buddy’s sister like a screen door when you’re still jerking it to the pics she’s sending you and sending her sexts back.

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But before we get to what’s going on in your pants, let’s talk a little about what’s going on in her head, shall we?

You’re her older brother’s friend. You treat her seriously, you’ve had deep emotional conversations and you’ve had some sexually charged banter… that sounds a lot like flirting to me.

Now let’s add to the fact that she’s got low self-esteem that’s been (in your words) making her act out. So not only are you flirting with her, but you’re bolstering her self-esteem and making her feel like an attractive, desirable person with plenty to offer some lucky guy or girl.

So: flirting, compliments, self-esteem boosts, naughty jokes, long, incredibly deep conversations…

You see where I’m going with this right?

From a reasonable outside perspective, this is looking like you were giving signs that you were into her. When she decided to toss out a test balloon to see if you wanted to take things to the next level—in this case, naughty pics and outright sexting—you responded in the positive and have continued to do so… except now that she’s wanting more, you’re telling her that you were never into her and this wasn’t what you intended.

Needless to say, these are some pretty damn mixed signals. When you add in the fact that she’s already got self-esteem issues and you’re now giving signs that she’s good enough to fuck but not to date… well, small wonder she’s upset.

Now, is that definitely what’s going on? Dunno… and neither do you, because right now you’re assuming a whole lotta facts not in evidence. And until you straighten things out, things are only going to get more complicated and unpleasant from here.

Normally, when it comes to dating or banging a friend’s siblings, I’m usually of the opinion of “it’s between two consenting adults and if their brother/sister doesn’t like it, they can put on their big-boy pants and deal”. But in this case… well, it’s kinda fucked up and it’s going to take some effort to un-fuck it.

The first step is, you’re going to have to stop sexting with your buddy’s little sister. As long as you’re saying “no, stop, don’t” while continuing to accept pics from her, it’s going to be pretty hard to believe that you mean anything you say. This means establishing some real boundaries, not token ones that crumble when she starts to tear up and you start getting horny again.

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The next step is going to involve a long, serious conversation with her. You two need to clear the air about what’s going on, how you got here, and where you’re going from here. You don’t want to hurt her? Then you need to start being absolutely clear with her about how you feel, how she feels and why you think that continuing this would a be a bad idea.

Because let’s be real here. Continuing this relationship in its current state is a bad idea and doing so just means the sister getting hurt and your friend getting seriously pissed when it looks like you were leading his sister on for your jollies.

Cut the sexting (including receiving them). Have that long and serious talk. You can still be friends, but you’re probably better off being platonic friends.

Good luck.

Hey Doc, I need your help.

I’m a few months from my twentieth birthday, and am dating a girl one year younger than me. It’s a relatively new relationship (we’ve been together for 4 months) but we’re sexually active.

(We were each other’s firsts, btw.)

Getting to my point, I have very little complaint about the sex. She’s a freak in bed, we communicate properly, listen to each other, satisfy each other (I hope). In short, it’s a pretty healthy sex life. Except for one thing.

I. Cannot. Make. Her. Orgasm.

For the record, she’s never reached orgasm, not even by herself, and because of this she keeps telling me that she believes it’s impossible for her to do so. I however, hold the firm belief that she can (that, and I feel a bit guilty at the fact that she can make me finish yet I can’t reciprocate, it just doesn’t seem fair). She tells me that the sex and foreplay is satisfying, even amazing in some cases, but that she just never reaches a peak point. We’ve tried everything, from oral sex (closest thing to achieving it), anal foreplay, different positions, roleplay, you name it. But no matter what we try, it may feel better, it may feel heavenly, it may feel eeeever so close, but she simply never reaches that point. I’m going crazy with the possibility that she might be right.

Is it possible that she physically cannot reach orgasm? Is it a fair sexual relationship if only one side is able to finish? I could use some help doc!

Sincerely,

Half Hour Marathon

First, let’s answer your initial question: yes, some people are anorgasmic. Approximately 10% of women can’t reach orgasm, either with a partner or through masturbation. There can be any number of causes ranging from physical (illnesses like multiple sclerosis, issues with the nerves, scar tissue on the clitoris, etc) to the mental and emotional to the chemical (SSRIs and other medications can make reaching orgasm almost impossible for men OR women).

Could your girlfriend be one of the unlucky 10%? Yes, possibly. It may well be worth your girlfriend’s time to talk to her doctor to rule out any possible physical problems or whether any medications she’s taking might be making it harder for her to get off. But remember: neither she, nor you, nor I are qualified to diagnose whether she’s completely anorgasmic.

(Remember: Dr. NerdLove is NOT a real doctor.)

So absent any medical issues, let’s talk about best sex practices. It’s good that you’re concerned with her pleasure, and that you’re working on figuring out how to make her feel amazing. The fact that you’re both experimenting to see what she likes and doesn’t like is exactly what you should both be doing. An open, judgement-free mind and a willingness to try new things are both key for anyone who wants to be a better lover.

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But one thing that may be keeping her from reaching orgasm is… well, you. There comes a point where focusing on getting your partner off goes from being a noble goal to becoming an obsession; there’s nothing quite as off-putting when someone is feeling pressured to “perform” as it were and get off. That’s a great way to end up making it impossible to get off.

Part of the problem here is that this is a very male-oriented form of thinking. Because it’s relatively easy for us guys to get off, we assume all sex needs to end in orgasm (especially ours). Women (and men) can and do enjoy sex without necessarily having their bell rung; the sensations, the emotional connection, the intimacy, all of it can be great even if she doesn’t have an orgasm. So as long as she’s telling you that she’s enjoying the sex and is satisfied, then take yes for an answer.

Of course, you realize this doesn’t mean that you get to take her pleasure for granted and just get yours. She may not be getting off the way you are, but she still wants amazing sex.

Assuming that your girlfriend is with you on this quest for glory and doesn’t need a break, then what you both need to do is simply relax. Pressuring her to cum is going to end up being counterproductive and end up making the sex exclusively about her orgasm and not about mutual pleasure or intimacy.

Now with all that being said, let’s talk about how to make this happen. My first question would be whether she masturbates or not. You say she’s never been able to get off on her own, so presumably “yes”. There are any number of possible follow up questions as to just how, where, when and how often, but let’s leave those aside for the moment and just assume that basic manual and oral stimulation hasn’t worked (yet).

So the next logical step is to introduce toys to the mix. Some women simply need more intense, direct stimulation than hands, tongues or penises can provide - but vibrators and dildoes can. Introducing some sex toys into your play can help make the difference between being just on the edge and going clean over the falls. If you live in a decent-sized city, you should look to see if you can find a good sex toy store; you want one that’s clean, well lit and organized with a knowledgeable staff, especially one that’s owned and run by women. Stores like Good Vibrations in San Francisco, Babeland in Seattle and New York, SheBop in Portland, Forbidden Fruit in Austin, the Pleasure Chest in LA and others all provide a comfortable, friendly atmosphere that makes shopping for sex toys more comfortable and the staff can provide advice to point you in the direction of the toys you want. They also frequently have classes on sex and sexuality which can help as well. If you don’t have one near you, most of the stores will also do mail-order. You should also try reading Erika Moen’s Oh Joy Sex Toy for reviews and tips on what you may want to consider investing in.

Let your girlfriend try some on her own, and then try adding them to your repertoire while you’re having sex together. Getting used to using toys as part of your time together will serve you in good stead, both with your current girlfriend and any future ones you may have. Many guys get hung up on the idea of providing a “look-ma-no-hands” orgasm with nothing but their peen… which ignores the fact that most women can’t orgasm from penetration alone. The more you’re willing to use whatever tricks and tools it takes for your partner to get off, the better of a lover you’ll be over all.

Another thing that your girlfriend can try (presuming she doesn’t already) is to practice kegel exercises. Many women need a certain level of muscular tension in their pelvis, abdomen and buttocks to reach orgasm. Practicing kegels—contracting the muscles that control the flow of urine midstream—can help with reaching (or even intensifying) orgasm. The kegel muscles contract during arousal and climax; tensing them during sex helps bring increased blood-flow to the genitals and can help get her where she needs to go. The stronger the muscle, the more tension she can bring to bear, which can push her past the point of no return.

But more than anything else, she needs to relax, emotionally. Getting stressed about whether she’s going to orgasm or not is going to decrease arousal, not increase it. She should focus on enjoying the sensations, rather than worrying about how long things are taking or whether she’s going to get off.

One final thing to keep in mind: this may simply be an issue that can only be solved through time and experience. Even today, many women come late to their sexuality; young women are actively discouraged from exploring their sexuality or to advocate for their own pleasure. Guys, on the other hand, tend to be masters at getting themselves off, having started almost as soon as puberty drops. So the problems your girlfriend is having getting off may go away as she gets to know herself better and becomes more confident in her sexuality. You can best help her by being a caring, patient, and giving lover. She may not be getting off now, but as long as you’re communicating, listening and paying attention, she may well be going off like a rocket in the future.

Good luck.


Do you have a story about learning to be a better lover? Ever hook up with someone you know you shouldn’t have? 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 doc@doctornerdlove.com and put “Kotaku” in the subject line.

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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 book Simplified Dating is available exclusively through Amazon. 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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