DEAR DR. NERDLOVE: Let me start by saying I’m a lucky woman – I’ve found someone kind and considerate, who makes me laugh and is entertaining and charming and who comes in to snuggle me before I go to bed even if he’s not going to sleep himself. There’s just one big problem – he has no job.

Part of it is my doing; I encouraged him to quit his job in December without having something lined up, which goes against my usual advice. However, the people he worked for were terrible; I have a high bulls

t threshold and these people went way past it. He once went to them with a complaint of sexual harassment by a female client – which made him profoundly and understandably uncomfortable – and they LAUGHED at him and told him he should be flattered! F

k that noise, I said.

So he left and I thought he was entitled to a nice Christmas to get over the frankly abusive practices he’d been dealing with. I thought once we hit January he’d start looking and everything would be fine, but no go. Then February. Then March. That’s when I started getting nervous.

I’m pretty good at writing resumes so I helped him with his (by which I mean I wrote it entirely). I tried to be supportive; I wrote him lists of places to call and apply to, I helped him with cover letters and went over what he could say in interviews. But still, no progress. He has a history of low self-esteem issues that I understand, having suffered similar issues myself. He’s convinced that his lack of education will hold him back and that spirals into him being worthless and then he feels like he’s not good enough for me and then generally ends in massive fight that upsets both of us for days. He seems to only be able to hit the panic button on hard issues. It’s like:

Can’t get job = I’m stupid and terrible = I’m the worst human being ever = girlfriend must want to leave me = why bother with making any changes = depression

Instead of

Don’t have job > try to get job > maybe fail to get job for a little while > eventually get job > everything’s fine.

It feels like I’ve tried everything: being supportive, getting mad/depressed (not in a manipulative way, I was just legitimately those things by turns) but I don’t know what to do. I come home and he’s spent the day watching TV or playing video games or doing his favorite hobby, and those things make him happy, which I love, but I feel like I’m not really getting a fair deal.

I make enough money to cover the rent (barely) so any other expenses are being covered by money I inherited. When I told him about it months ago we discussed it being used for our wedding and a house and vacations, etc. but now we’re blowing through it at a rate I’m not comfortable with. He has big dreams and likes to talk about what we’d do if he won the lottery and how I wouldn’t have to work – but I actually like working. I don’t need him to be a millionaire, I just want him to be my partner. He’s my one and I’m in too deep to leave this situation but I’m looking down the barrel of a 50+ year partnership with me being the responsible one and I don’t think I like who that might turn me in to.

All I want is to know how to help him see that it’s not the end of the world – he just has to do some work!

Them Money Troubles

DEAR THEM MONEY TROUBLES: So if I were to keep things short and sweet, then I’d say this: your boyfriend needs to grow the f

k up.

Let’s be real here: dude’s coasting along. He’s content doing his own thing because hey, why not. Right now, nothing’s his fault or responsibility. He’s able to sit playing video games and watching TV all day and when he’s feeling particularly down, he can do the I SUCK I AM THE WORST PERSON IN THE WORLD dance and have you fall back into support mode.

Now I’ll freely admit: this sounds pretty damn harsh. I actually have a lot of sympathy for him. I’ve dealt with self-esteem problems; I get what it’s like to feel like you’re stuck and that every option you have is awful. I especially get the vicious cycle of feeling like a loser, which makes you depressed, saps your drive and motivation and then your continued inactivity makes you feel like an even BIGGER loser. His last job sounds like a nightmare situation (not to mention a reminder that yeah, guys get harassed and the support structures aren’t there to handle it) and the economy still seriously sucks for people who’re out of work, and half the jobs out there are gig-economy crap or “efficiency”-driven nightmares that exploiting the workforce and screwing them out of the profits of their own labor.

But there comes a point when he’s gone from being a grown-ass man to just indulging himself on your dime. Hell, from the way you’re describing things, it doesn’t even sound like he’s doing housework or otherwise contributing in ways besides financial. I could (maybe) give him a temporary pass if he were at least keeping the house clean or handling the cooking instead of dumping that on you too. But he’s not. He’s enjoying his games and dreaming his dreams and the nice thing about dreams is that you never have to do anything about them. That’s for Future Boyfriend to worry about, not for him!

You may think he’s Mister Awesome, but right now your dream man is busy letting you do all the hard work while he’s sitting back and contributing nothing. You want a partner. He wants a mom.

Unless that dynamic changes, this isn’t going to work out; you’ll be out a relationship and your savings. Not every relationship is going to be perfectly egalitarian but right now there’s no exchange here.

S

t’s got to change.

So what do you need to do? You need to apply boot to ass.

It’s to start being the demanding bitch you’re worried about being because he’s just going to slide on by until you are. So you need to tell him: it’s time to get a job. Period, the end. He may not be able to get a job immediately but he needs to be making concrete progress  – not bulls

t head-fakes in the general direction of work that buy him some time. And until then? He’s cut off. Turn off the money spigot. No funding his laziness, no buying anything that isn’t rent, utilities and groceries.

Hell, consider cutting off the cable while you’re at it. It’s going to suck to have to forgo some of life’s luxuries but the fact of the matter is, he’s being a leech. It’s time for him to start coughing up his share of the workload and money for the bills.

And then you need to ignore his wee tantrums, because quite frankly they’re a derailing tactic. As soon as you start getting angry (or just, y’know, stern) at him, he goes into his song and dance about how awful he is and how you want to leave him and so forth and so on and now you’re no longer talking about getting a job, you’re stuck reassuring him that no you’re not about to dump him and there there there. So now he’s cornered you into being his enabler. If you push him to actually suck it up and take care of his responsibilities, then you’re the controlling bitch who tries to rule his life and doesn’t let him have some fun and if you push it further, then suddenly his self-esteem issues come roaring back to make you back off.

Unfortunately, the only thing you can really do is treat it like a tantrum: let him rant and rave and cry until he wears himself out. Then stick him in front of the Zip Recruiter login page and tell him to start applying.

Now here’s the thing: it’s entirely possible that he’s dealing with depression, which is contributing to his lack of motivation and his inability to actually get up and do the things he needs to do. Depression is a vampire and it can suck the life and the energy out of you. I have been there, done that and started printing the t-shirts. But dealing with depression doesn’t mean that he no longer has responsibilities — to himself, or to you. If he legitimately is dealing with depression — instead of weaponizing his low self-esteem as a way of getting out of trouble — then he needs to address that too. But neither of those can happen from your couch. He STILL needs to be doing the work (and getting work) and if he needs a boot to ass to get up and do something, then so be it.

It ain’t gonna be fun. It certainly isn’t going to be pretty. But it IS necessary. This is one of those times when being the jerk is going to be the kindest thing you can do… because being nice is just going to mean the end of your relationship.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)

DEAR DR. NERDLOVE: I’m trying to figure out if I like my best friend’s sister and if she likes me back. In other words, I’m trying to see if it’s worth the pursuit. I don’t get to see much of her often but I think about her more than any other girl; I’m introverted and shy so I don’t keep in touch with a lot of my girl friends all that often. Oddly enough, I’ve known her since I was 12 and she just was eight years, I’m 25 and she’s now 21. I’ve kept in touch with her longer than any girl I’ve ever known. I definitely understand that a lot of this might just be that I’ve never been with anyone before and since I’ve known her the longest, I think I can certainly trust her if our relationship develops into passionate one.

One of the things stopping me is that her brother is protective of her. I completely understand this, but frankly, she is old enough to make her own decisions. Also, I think if she was interested she might’ve given me better clues. Although to be honest, I would guess she’d know me well enough to know that I would be very intimidated to start dating the little sister of my best friend.

Since I’ve discovered I had a crush on her, I’ve gone to the trouble of mentioning she looks nice, that I noticed she changed her hair, stating I was shocked she didn’t like how she looked, etc. Sometimes, when we’re all drinking altogether I’ve made sure she gets plenty of water and just makes sure she’s all right. Her stepmom has even commented that I would be a good match for her based how I treat her. However, I think it more like a carefree joke… and I was so embarrassed that I couldn’t say anything.

I’m just not sure how to go about talking to her about this; not just because of her protective brother but because I’m often a bit more sarcastic and I worry she might not take me seriously. If it’s just a simple crush do I even say anything? If I say anything to her about it, do I risk losing my best friend? Maybe I’m reading too much into this but she’s been dating a lot of guys who are ofter shyer than me and even some have looked a bit like me. She does go out of her way to introduce me to her boyfriends and they do seem to be a little protective, almost like they’re jealous. (If I knew better, I’d suspect it to be very Aaron Sorkin-esque relationship.)

Based on how complicated things are, I’ve been trying to meet other people. I’ve made a point to talk about other girls that I’ve gone on dates with and how I wasn’t very compatible with them. On just the couple of occasions that I’ve talked about girls she’s been strangely silent, even to the point where she actually leaves without a word. Her only advice was that she could see me with someone as young as 20. With other friends in our circle she’s a bit more curious how certain things have worked and what didn’t.

I’m trying to figure out if there’s something between us but I worry about what my best friend would say if he found out… I don’t know who to talk to about this stuff.

Stumped Over Sibling

DEAR STUMPED OVER SIBLINGS: Can we cut the bulls

t a little, SOS? Because between you, me and the entire Internet, it’s pretty safe to say you’re interested in your bro’s sister. You don’t need to keep hemming and hawing and throwing conditionals in there to make it sound like you’re not sure if you’re into her or not but you THINK you might be but…

Just be real here. Your buddy’s sister got hot, you have a thing for her. It happens. And that’s fine, man. You’re both adults. The fact that you’ve known each other all this time doesn’t preclude you from recognizing that she got cute, nor does it mean that she’s off limits because you two grew up together. It’s not like you’ve spent all this time waiting for her to come of age. You both grew up, you matured, you changed and now you’re starting to see her as an adult woman instead of an adjunct to your best friend.

So it’s not that you don’t know whether or not you’ve caught feels for her. It’s the potential for unnecessary drama you’re worried about that makes you hesitate to declare that yes, you’re into her.

But before you worry about your buddy, you should decide what you’re going to do about HER. After all, she’s the one you’re interested in, so she’s the one who’s going to be the one to decide whether or not she’s interested in you, too. If you’re interested in her, you should probably find out how she feels before you worry about literally anything else.

And to be perfectly frank, running to her brother for permission is a wee bit patronizing. Doubly so considering that she’s a grown-ass woman. Family is family and they certainly get to have an opinion, but they don’t get veto power – either overtly (“No, you can’t date him, sis”) or by fiat (“Talk to my sister again and I’ll kill you”) over her love life. So if you’re interested in her and want to try to pursue something with her, then maybe you should run things by her first before you worry about her big bad bro.

Of course, you’re not sure how she feels about you. You think you’ve been getting some hints, but the ol’ Magic 8-Ball keeps coming up “Signs Hazy, Ask Again”. So what do you do?

Well, the way I see it, you’ve got two choices. You can spend weeks and months trying to read the tea leaves and divine her intentions from subtle little things that may or may not mean anything. Or – and stick with me, this is a little crazy – you could always ask her out on a date.

Extreme, I know. But it’s a fairly reliable way of finding out if someone wants to date you.

If the two of you are into one another and you’re going to pursue this more than just the odd date or two, then you can worry about her brother. It’s entirely possible that this would be something he couldn’t possibly tolerate and it’d put a strain on your relationship with him. At that point — and not before — would you have to decide which is more important: your friendship with him, or your relationship with his sister.

But if he’s your friend and he knows that you’re a good guy who would be good for his sister, then that shouldn’t be as much of a conflict. It could be difficult if he does have a freak-out – especially since that’s insulting to both you and his sister. 

But as I said: he doesn’t get a veto.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)

DEAR DR. NERDLOVE: I’ve read some of your articles and wanted to first off say thanks! So here’s some details about myself:

I’m a 30 yr old male with a successful career. I’ve never had a hard time attracting attractive women but I’m very sexually inexperienced due to failed sexual encounters, lack of confidence and anxiety, which I believe has led to 0 serious relationships.

I got into porn at a very young age (13 maybe) and masturbate to it regularly with the initial emphasis being to get it over as soon as possible. I always lie on my back in bed while doing so and have never deviated. I also started with a squeezing motion at a young age as opposed to an up and down motion so I’m guessing I’m the victim of the dreaded “death-grip”. Only in the past few years have I adopted the stroking motion but still apply heavy pressure, especially near climaxing.

Upon my first sexual encounter (age 25) and numerous encounters thereafter, upon penetration, I go from erect to completely soft almost instantly. During foreplay I’m very aroused, and seldom never “lose it”. In addition, I’ve experienced situations where I get only like 70% of an erection, where I can’t even penetrate. Upon failure, I go to 0% and that’s pretty much game over.

I get great morning wood (100% erection) and can get these when masturbating alone, typically after smoking marijuana. Otherwise, I get about 70% when sober.

No woman has ever been able to get me to orgasm via oral, either

Now that I’ve set the table a bit, what can I do to get better in the bedroom and get/keep 100% erections? I find myself fearful of evening trying anymore due to the embarrassment that follows after failed performances. I just want to be able to make love like a normal person! I’ve already started working out and trying to eat healthier but any tips or advice at all to try would be immensely appreciated!

Thanks in advance!

Junk For Junk

DEAR JUNK FOR JUNK: You have two issue here, JJ.

The first issue is simple. You’re absolutely right: you’ve basically carved a groove into your erotic brain and that’s interfering with your sexual response patterns and making it impossible to get off when you’re having partnered sex.

You’ve set yourself up with a very specific pattern for when you masturbate, and since you never deviate from it, it’s become more or less what you need to get off. That’s going to be a problem, because people are almost never going to f

k the way you jerk off. You’ve trained yourself to need very specific form of stimulation — that squeezing motion you mention — that simply isn’t something that the human vagina, anus or mouth can recreate. Just as importantly, you’ve taught yourself that you need a level of pressure that, again, internal muscles will never be able to match. As a result, penetrative sex is never going to get you to where you need to go, leaving you frustrated and less than 100% solid.

Now the fact that you trained yourself into this pattern means that you can train yourself OUT of it. It’s just a lengthy and difficult process. The key is that you need to starve yourself of sexual stimulation, to the point that your junk, your nerve endings and your brain are all desperate for ANY sort of contact in order to get off.

So you’re about to go on a fap-free diet from now until… let’s say, Halloween to start. That means that you now have a strictly hands-off policy with your penis. It is now purely for urination and decoration. You don’t touch it except to use the urinal or avoid getting caught in your zipper. You do not masturbate. At all.

The point of the exercise is to to let that frustration build and build until you can’t take it any more. And then you let it continue to build because you’re not there yet.

This is going to be difficult. REALLY difficult.

(Notice how carefully I refrained from saying “this will be hard”. Appreciate my restraint.)

You’re going to want to get off in the worst way. You are going to feel like you’re at the bursting point and surely by now you can take matters into your own hands.

Well, no. Not yet. It’s still too early. And don’t call me Shirley.

When you reach the point where you think your prostate is about to explode because you are just THAT backed up… then and ONLY then are you allowed relief. However, you’re NOT going to use your usual masturbation habits. You are forbidden from jerking it — or squeezing it, really — the way you always have. You’re going to switch things up. You’re going to use your other hand. You’re going to use a feather-light touch. You’re going to get yourself a Fleshlight or a Tenga Flip and some lube. You are going to take things very slowly, instead of the “get it done as fast as I can” method you’re used to. You’re going to do ANYTHING other than using your squeeze-play… which, I note, you’ve been falling back to even when you’ve been trying to switch things up.

The point of this exercise is that once you’ve starved your penis to the point that it’ll accept any stimulation is to carve a different groove in your brain — one that’ll let you be able to get off through standard penetrative sex with another person. That’s why you need to start getting yourself in the habit of using techniques that don’t use a literally impossible level of pressure or friction. If you use your old technique, all you’re going to do is reactivate those old neurons and fall right back to where you were before, with a penis that won’t respond to anything but your very idiosyncratic masturbation technique. So from now on, your squeeze-technique? It’s off-limits, because no human body can replicate that level of pressure.

But here’s the other issue you’re having: your inability to get off with another person has destroyed your confidence and without confidence, your boner simply isn’t gonna work.

Erections are like faeries in Peter Pan: they only work as long as somebody believes in them. They’re little divas who want everything to be perfect and if anything is even a smidge off, they’ll throw a tantrum. That’s they melt like the Wicked Witch of the West as soon as you don’t believe it exists.

(Yes, I just crossed the fictional streams; I’m on a roll here.)

You were already anxious about being with someone else and so you were less than rock steady and ready to go; instead it was more like trying to shoot pool with a rope. Once that anxiety became part of your experience, your worries about being unable to come or to please a woman have become a self-fulfilling prophecy – you’re expecting to lose your erection, and so you do.

The solution here corresponds with the solution to your breaking your death-grip cycle: take penetration off the table. Your fingers never go soft. Neither does your tongue. Neither do sex toys. So bring all of those into play. Use your fingers on your partners like you’re back in high-school. Go down on for so long that you’ll have to learn how to breathe through your ears. Use a vibrator on them.

This will not only have the benefit of taking the fear of a soft or non-existent erection out of play, but it’ll make you a MUCH better and more desirable lover. Most women can’t achieve orgasm through penetration alone, and men rarely give enough time to foreplay. The more practice you have at pleasing women that aren’t centered around your penis, the better you’ll be overall.

And when it’s time for them to reciprocate… they can give you hand-jobs or oral, but no penetration until you’re starting to get past the whole “I can only orgasm in this one, incredibly idiosyncratic way.”

The more you start to realize that there’s more to sexual pleasure than just your penis, the more you’ll realize that not rising to the occasion isn’t the dilemma you think it is. It just means you switch gears and use the other tools you have at your exposure until you ARE ready.

It’s a matter of practice, endurance and some willingness to clap your metaphorical hands if you believe… but you’ll get there.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)