Hello, Internet! Welcome to Ask Dr. NerdLove, the only dating column to be stranded on a hellish island with only one goal—to improve social skills.

This week we’re talking about habits, and how to get used to doing the things we need to do. One reader has trained his body to only respond to certain stimuli and needs to re-train himself so he can enjoy his relationship with his girlfriend. Another needs to learn that she doesn’t have to let social anxiety and loneliness allow people to make her uncomfortable.

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It’s time to start enforcing some positive habits. Let’s do this thing.

Hi Doc,

So I’m a 31 year old male who’s recently gotten my first girlfriend/sexual partner. We have great emotional/physical chemistry and we ended up naked in bed with each other on our third date. I had no problem at all making her orgasm with my hands/mouth, and she turns me on a lot so I have no problem getting an erection when I’m with her.

However, I haven’t had an orgasm with her yet. She’s tried stimulating me with both her hands and her mouth but no luck there. When I penetrated her she came very quickly but I wasn’t able to achieve orgasm.

This isn’t a downside to our relationship (so far) but I would like to fix this if I can. The most likely cause is the fact that I’ve been masturbating using a certain style for my entire life, and obviously oral and vaginal sex is a completely different experience. It might be an emotional issue, but I don’t feel that it is since we’ve been extremely open with each other and talked about everything (including this issue) and I honestly don’t feel anxious when we fool around.

In my attempts to solve this problem I’ve decided to ditch porn (which has been incredibly easy to do since she entered the picture), and I’m going to cut back on my almost daily masturbation habit (maybe once or twice a week when I’m on my own). I’ve also heard that if I do have to masturbate I should start doing it with my left hand, or try doing it with a condom on since this is different from what I’m used to.

Are there any other suggestions for “reprogramming” my brain to get used to non-masturbatory sex?

Regards

I’ll Finish Later

You have a fairly common problem, IF; you’ve trained your dick to only ejaculate in response to very specific stimulation. It’s not just that penetrative sex is a different sensation, it’s that it’s different.

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One of the quirks of the human brain is that we build up habits fairly quickly, and the more we do them, the more we carve a metaphorical groove into our brains. This is true regardless whether we’re talking about physical habits or something as ephemeral as your outlook on life. The more you do something, the more you reinforce it in your brain and the more it becomes part of you - something that you can use for good or for ill.

The problem is that the fact that something is familiar and routine doesn’t mean that it’s good for you… but your brain doesn’t care. Your brain is lazy and doesn’t want to change because it’s easy to stay in the same rut than it is to get out of it. In fact, it’s so lazy that it will actively fuck up your attempts to change. If you’ve ever tried to quit, say, cigarettes or Diet Coke, or change your eating habits, then this may feel familiar: you’re doing great until one day BAM!: you get hit with a craving like an out of control freight train being driven by Terry Crews. This is known as an extinction burst; your brain realizes that it’s about to lose all the sensations and stimuli it gets from the old habit for good and floods your system with demands to do the thing one more time.

How is this relevant to your problem? Well, I’m glad you asked (and that you’re allowing me to put words in your mouth): it’s because the cure to your problem isn’t to cut back on masturbating; it’s to stop entirely.

Don’t worry: I don’t mean permanently. But it is going to be a while. See, you need to starve your brain (and your dick) of those familiar sensations. You’ve carved a groove into your brain and if you masturbate the way you have before, you’re just going to continue to reinforce that pattern. The fact that you’re only doing it once a week just means you’re still using the same sensations, just spaced apart. The only way you can break yourself of this habit is to go cold turkey until your dick is so starved for sensation that it’ll take anything.

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Of course, this doesn’t mean that you should neglect your girlfriend. Continue to make out, roll around, go down on each other, even have sex. But if you want to get off, someone else needs to do it for you; if you do it yourself right now, you’ll almost certainly fall into that same pattern of jerking off the way you have been for years.

You’ll know when you’re reaching that tipping point because you’ll be hit by an extinction burst; you’ll be dying to just rub one out. Resist the urge and get your girlfriend to give you a helping hand instead.

Once you’ve started getting off in ways that don’t involve your old jerking habits, then you can start masturbating again… but you need to remember to vary the ways you do it. Use a Fleshlight or a Tenga Flip. Use lots of lube, very little lube, switch hands, do it with a condom on… keep yourself (and your dick) guessing. Variety isn’t just the spice of your sex life, it’s how you avoid a monotonous pattern that makes it harder (har) or even impossible to get off with another person.

Good luck.

Dear Dr. NerdLove:

I’m a 20 year-old college student. I’ve been in a relationship with my current boyfriend for two years. Recently, I’ve started using Facebook and got into contact with some people from back home, in particular my ex-boyfriend from my senior year of high school. He’s a fun person to talk to, and I never really considered our relationship to be too substantial so I saw no harm in reconnecting.

A few weeks ago, he confessed to me that he was still in love with me, which was surprising because I didn’t think our relationship extended much past a mutual taste in video games and a similar sense of humor. I told him the feeling wasn’t mutual, and he didn’t talk to me for a few days. I know he’s pulling the “nice guy” card since he used that a lot when I knew him. I always get upset when guys pull stunts like this, since my severe social anxiety convinces me that I’ve done something wrong.

He talked to me about a week later and it relieved my concern that I had done something wrong. However, even though I shut him down, he’s been hitting on me ever since, and is getting increasingly more aggressive. He’s one of the only people other than my boyfriend who I can talk with about games and computers, but his behavior makes me really uncomfortable.

I’ve kept my current boyfriend in the loop with my ex’s unsettling behavior, and he thinks I should break off all contact with him - unfriend him on Facebook, stop talking to him altogether, etc. This also makes me uncomfortable because I don’t want to veer into territory of my current boyfriend totally controlling who I do or don’t talk to.

I’ve had a hard time making friends with interests that align so closely to mine, and I have enjoyed chatting with him recently. Is there any way to shut him down without totally breaking off contact with him? Or without getting him mad at me?

PLEASE HELP

Sincerely,

Taken and Confused

Hey, I totally get where you’re coming from T&C; it’s completely understandable that you don’t want to get into the habit of letting your boyfriend dictate who you can and can’t be friends with.

Now someone call Sir Mixx-A-Lot because there’s a huge “but” coming…

BUT.

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I hate to say it but your boyfriend? He’s got the right idea. Kind of.

See, right now your ex is trading on your social anxiety, knowing that your discomfort means that you’re going to let him keep getting away with his shitty behavior. He knows you’re uncomfortable with the way he’s hitting on you but the fact that he keeps on doing it tells you that he doesn’t give a shit.

So what do you do? Well, it’s time to start enforcing your boundaries. If you want to keep this guy in your life, then you need to lay down the law: it’s time to stop with the aggressive flirting and hitting on you. Ya’ll can talk about video games and computers and TV and what-not to your heart’s content but dating? Off the table. It’s a no-go area. If he starts hitting on you, then you tell him firmly: “We talked about this. I’m not interested, and you’re making me uncomfortable. Stop it.”

If he does it again? Then you be firmer: “I’ve told you how I feel and if you keep doing this, then we can’t be friends.”

A third time? Well that’s when it’s time to take the nuclear option and cut him out of your life: unfriend him on Facebook, block him on Twitter, Kik, Snapchat, WhatsApp and any other social network you’re on. He had his chance and now he no longer gets to have access to your life. It’ll be hard. You’ll feel awful doing it. You’ll feel like you’re being an awful person. But here’s what you need to keep in mind: he has shown you, repeatedly, that he does not care about your boundaries. He doesn’t care about you, only himself, and that is the kind of toxic friend that you don’t need in your life.

Like I told Slightly Creeped Out Girl back in March, he may try to make you feel bad for having boundaries. He’s going to trade on your social anxiety to make you question whether you’re doing the right thing. Trust me: you are. You’ll feel like you’re being a bitch. GOOD. Sometimes you’ve got to embrace being a boss bitch and put a motherfucker in his place. And if your ex is continually pushing against your boundaries, then his place is on the Nope Train to Fuck This Shitville.

I know it’s hard. You’re probably getting the anxiety chills just thinking about doing this. Trust me: it’s worth it. You don’t have to take letting your ex creep on you as the price of having someone to talk games with. You deserve better than that. You can and will make new friends, better friends, to talk to about your favorite activities.

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Establish and enforce your boundaries. If he refuses to respect them, then he won’t respect you and it’s time to kick him to the curb.

You’ve got this. Good luck.

Have you broken some bad habits? How have you dealt with toxic friends and unreasonable exes? Share your stories in the comments and we’ll be back in two weeks with more of your questions.

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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.

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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Illustration by Jim Cooke.