Gaming Reviews, News, Tips and More.
We may earn a commission from links on this page

Ask Dr. NerdLove: My Womanizing Roommate Gave Me Awful Dating Advice

We may earn a commission from links on this page.

Hello all you celestial cephalopods of sin, and welcome to Ask Dr. NerdLove, the only dating advice column to scale the heights of Yggdrasil.

On occasion, I’ll get a letter from someone that requires a more in-depth response than the typical question for Ask Dr. NerdLove. Instead of the usual answer, these letter writers require some exploratory emotional surgery to find out just where things went wrong, what they should have done, and what they can do to do better next time.


And then sometimes we get questions like this one, asking for help with an ongoing situation. So come up to the lab and let’s see what’s on the slab. Bold text is from the letter writer, regular text and images are from me. It’s time to do this thing… boy.

Hello Dr. NerdLove,

I know this may be a long shot to get a hold of you but I figured I’d take the time to write you to get a second opinion about my roommate’s views on women and dating.


This is the sort of intro that sends chills up my spine. This is the dating advice equivalent of the old man telling the teenagers not to go to the old abandoned summer camp or not to read from the book bound in human skin.

More seriously, however: I’m a big believer in trusting one’s instincts. While there is a lot of bad advice out there, especially if you have little social experience, more often than not, if something sets your Spider-sense tingling, there’s a reason for it.

Me personally, I’m a 28 year old virgin who’s never dated, let alone made out with anyone. Didn’t even really hug a girl til I was 18 years old. A lot of that due to family and personal bullshit that make me feel like I’m not really worth dating (money, career, weight, etc.).


Let me stop you there, chief. Some of the biggest, most pernicious myths in dating all start with “here’s what women want in a man” and usually run in that exact pattern: money, career, weight, etc, with etc. covering a range of sins from “be alpha” to “have a dick like a two-by-four” or “treat them like shit to prove you don’t care.”

Somehow that advice never runs to “be a good man with strong personal qualities to offer” or “know how to make her laugh, feel desired and feel safe with you.”

My dad never really had a clue about dating or what advice he could give other than “find a pretty lady you like” or my mom who would say “find a lady and give me grandchildren. Also stop being fat.” I also never really had friends to help teach me the ways of dating, either since most of them were either clueless or I didn’t really have very good friends at the time. So a lot of that has gotten in my way and it is hard for me to get past and I feel like my life is ticking away.


Reality check: you have all the time in the world. There is no mythical window where you have a chance to get a partner and if you miss it, then you’re shit out of luck. Some people are lucky and get an early start. Some folks have a natural instinct for social interaction or are gifted with natural charisma.

(we hates them, precioussss)

Others take a little longer to get to where they need to be, and that’s fine. There’s nothing wrong with being a late bloomer. Sometimes the best dishes are the ones that take the longest to cook. And — straight talk — many times, people who lose their virginity later make for better partners in the long run. They tend to have their lives in order and are in a better position to appreciate what their partners have to offer instead of always looking for the next good time.

I’m a super nerdy dude who enjoys playing fighting games with friends on my days off, streaming and sometimes traveling to play.

One year ago, I decided to move out of my families place and moved in with my roommate. We were somewhat friends before hand playing fighting games together at times. My roommate bangs a lot of girls. Like, I mean everything within a 50 mile radius of our apartment. Almost every night there’s a new lady coming over. I know this because I end up meeting them or hearing them *cough*. They range from fairly overweight to super model skinny, ages 20-40, child-free or moms. Some of them nice and ditsy, or borderline psychotic.


There are two things to keep in mind here. First: it’s easy to rack up numbers when you’re willing to take on anyone.

Second: sheer numbers don’t mean much in and of themselves. The guy who has a 50 year relationship with one woman is as valid as the guy whose bed collapsed from all the notches in the bedposts. And just as importantly: the number of partners you’ve had isn’t a predictor of how good you are in bed. The reason why some folks have had lots of sex is because they’re great at attracting women but not so good at actually pleasing them. Their bullshit only gets them so far, and that doesn’t usually result in repeat visitors.
Sexual skill is far more about what’s between your ears than what’s between your legs and has next to nothing to do with the number of partners you have or haven’t had.

Apparently, he has a huge dick too since that’s what I hear from the women he bangs. Most of them bring him food, others come over just to bang, and some are there as possible girlfriend material.

My confusion sets in when he tells me he only bangs the women he has some connection to. That the women he brings home he likes something about their personality.

He also says that a lot of the women he bangs are his friends. That he talks to all these women, that he hangs out with them all and that he tells the women he’s with that he’s hanging out with all these other women. I mean, his phone is filled with messages from all these women and he tells me they are all his friends?


While I question that he’s telling the absolute truth here, this is actually a fairly positive philosophy overall. I’m a big believer in only sleeping with people you could enjoy talking to if sex weren’t on the table; it helps cut down on the amount of times you wish you could un-fuck someone.


It also helps when one recognizes that attraction is a multi-axial thing. Someone may not necessarily be in the top percentile in the looks department, but there are other aspects of them that gets your motor rev’d up and ready to go.

How does that work? How does every girl just accept this? He would have to be playing some game with them in my opinion.


I’m going to go ahead and guess that not all of them are accepting this. In fact, I’m going to go ahead and guess that many of these women don’t know the others exist.

It’s certainly possible that he’s leading some of them on. It’s just as possible that he’s playing semantic games and not disabusing them of the idea that there’s more to their relationship than just friendship and banging. Or there may well be people in his group that aren’t listening when he tells them that this is just a friends-with-benefits relationship.


The more likely possibility is that he doesn’t have that strong of a connection with them. While he may stay in contact with them initially at first, I would doubt he’s putting in the effort to keep a friendship alive and well.

But while I’m here, let me belly up to the side-bar: Lots of men like to think about trying to maintain a harem of FWBs and girlfriends; very few ever think about what that means, logistically. Anyone who’s been in a polyamorous relationship can tell you: trying to maintain a relationship with one person is tricky. Two requires varsity-level time-management skills and three (or more) is a full-time job in and of itself.


It’s easy to fantasize about having sex on tap with no real effort on your part. You call or text one of your regulars and they come over like you just ordered a pizza. In practice, however, what happens more often is that you find that women are willing to see you once or twice before starting to not take your calls or respond to your texts because let’s be real: the sex ain’t that good.

Even with pure fuckbuddy relationships, where sex is the only point, there’s some relationship maintenance involved. People don’t like feeling like a Real Doll with a pulse, even if the other person has a magical dick or gold-plated vagina. Treating someone like a person, even if the sum of your relationship is tab-a-into-slot-b. is a big part of what makes one person a masterful lover and the next a “God what was I thinking” story over drinks.


I suspect if you were to track your roommate’s various partners, you’d see that there’s a much higher turnover than you realize. Getting someone into bed isn’t the same as being able to get them to come back.

Another thing is he was telling me that he has a dick pump and that it’s saved some of his relationships when he couldn’t get hard.


That… kind of puts a bit of a lie to what he said earlier. A hard dick isn’t the end-all/be-all of attraction, but if he’s having to break out a pump, cock-ring or pill on the regular with women he’s bringing home or someone he’s dating… well, that’s a sign that maybe he’s not as into them as he claims.

That his relationship with his former girlfriend wasn’t working out cause she gained some weight and he couldn’t bang her any more cause he wasn’t attracted to her any more. Also because of some weird personal feeling towards each other I guess?


It’s weird cause I moved in after they broke up and she would still come over and hang out. They still shared a vacuum cleaner, letting her borrow it from time to time (months at a time) for some reason.I ended up buying a vacuum cleaner because I got sick of not being able to keep the house clean, then all of a sudden she stopped coming over, which I thought was odd.


I’m going to go with “hey, you don’t make my penis smile so get out,” here.

He also still uses her Amazon Prime account to buy things.

I’m starting to take back my praise for his philosophy.

I had asked him for advice on Tinder once and he helped me put together a profile to help me meet women. The problem was the stuff he wrote for me didn’t really sound anything like me.


And that’s going to be a problem. One of the common mistakes people make when they write dating profiles, whether for Tinder, OKCupid, Bumble or Coffee Meets Bagel, is that they focus on what they think women want instead of selling who they are.

This is fine if all you want to do is jerk off your ego over how many matches and messages you are getting. But the point of online dating is the dating part. At some point you’re going to actually meet and that’s when you have to actually live up to the bullshit you (or he) wrote.

Like the material itself was really good and I could see it being enticing to most women, but I felt it really wasn’t saying anything about the kind of person I am. It felt more like a lure just to draw women in. It said something about “Power tools and commitment” and some other well written generic bullshit.


On the one hand, that’s a good line. On the other hand, that’s also a line that’s going to get you called out for using a line. And while that can work — I’ve used similar lines specifically to get people to respond — if you don’t have the personality to fire back in an appealing way when someone calls you out, it’s going to go over like a lead balloon.

I know how to use power tools and all that, but it just felt like an uncharacteristic thing about me.


Trust me: knowing how to use power tools is the least of your problems here.

I also don’t really have that many pictures of me personally available digitally on Facebook or anything, so the few single shot pics of me I used were from 2 or 3 years ago. He said it may be “somewhat fake”, but it’s suppose to draw if women so when we actually talk, they can get to know me then.


Funny thing about this technique: most women aren’t going to appreciate the fact that you were bullshitting them, especially once they’ve actually taken the time out to come meet you in person. That’s time that you’ve wasted, time they’re not going to get back. Time that could be better spent doing more important things, like comparing toilet paper brands.


The number of women who’ll be ok with the fact that you lied to them is so small that I’m not sure scientists have actually invented it yet. And the ones who are ok with having been lied to are sending up signal flares that they are not women you actually want to date.

The problem is that you are still somewhat lying to them and that doesn’t make me feel good about it.


Adding an inch to your height is “somewhat” lying. Creating a profile out of whole cloth and outdated photos is a lot of lying.

In the end, I never actually swiped or talked to anyone. I just deleted my whole profile.

I ended up telling him that I hadn’t really done much with Tinder and got rid of my profile. He told me to look at his to maybe get ideas. His first pic was of him with no shirt on, head cut off in the picture, holding a belt, wearing jeans, and kneeling on his bed. The rest were normal pics and one of his dog.


The dog will work far better than literally anything else he’s suggested. Also: do not borrow someone else’s dog for your dating profile.

I asked why he had the cut off head pic? He said it was to dodge any of the other women who came looking for him that were angry with him.


This is the point where I would’ve stopped listening to his advice and started trying to back away slowly.

Also he had a different name.

… so at what point did you start questioning the wisdom of listening to your roommate, exactly?

I thought it was a bit odd,


but there was the on lady he banged that ended up sending him death threats on his phone so he had to get a new phone number.


My roommate is also a weirdly hopeless romantic (I think).

I agree with two thirds of this.

I really have a hard time believing anything he says.

Then why in pluperfect hell are you asking him for advice?

He says he wants a serious relationship and to settle down with someone. When he finds a girl he likes, he ends up deleting all his apps and dating profiles (I’ve seen him do it). He then gets serious and it’s all about her. At least, until the girl says he can bang other women.


The professional term for this is “douchebag”.

He says he can still hang around and bang other ladies until their relationship is finalized as boyfriend-girlfriend.


While this is technically true — I’m a firm believer that you aren’t exclusive until you have specifically had the Defining The Relationship talk — something tells me that your buddy is letting women believe they’re exclusive, even when they aren’t.

To me personally, that seems a bit odd. A lot of his more serious relationships have lasted from between 3 - 7 months outside of his last ex which was for 3 years.


That seems about right; this is approximately the length of time it takes for the New Relationship Energy to quit papering over the fact that he’s kind of an asshole.

Being that me and him are (technically) friends, we also hang with some of the same group of people. The problem is he doesn’t really hang around anyone that doesn’t have a vagina for very long. Our friends we’ll be like “Hey, come over today or tomorrow” and it’s always “Sorry, I have pussy plans tonight.”


Like, I get that if it’s every once and a while, but it’s every single time he’s invited over to hang out. The man is reclusive, returning to his room to watch Netflix, only leaving when the ladies call. He literally does nothing but fuck, eat, Netflix and sleep. After a while, he also stopped playing video games all together, never playing fighting games with any of us.


OK I want you to reread these last two paragraphs. Let them wash over you. Roll them around in your mouth like a fine wine. Now ask yourself: is this what you want life to be like?

This is a serious question; some folks will indeed want exactly that. But something tells me that this is not you. But this is the life he’s built for himself and everything he does is in service of living this particular lifestyle. All trying to emulate it will do is give you a life similar to his. And if that’s not what you want… well, then I’d suggest you stop listening to his “advice”.

I don’t know anymore who this man is. It feels like any time he gives me advice it’s more about getting the lady interested as quickly as possible with whatever means. I’ve seen him hit on ladies before and it just seems he ends up talking over them and using his pretty enthusiastic personality, but they end up going back with him to bang so does that mean his methods are successful?


It’s successful in that yes, he’s getting laid. Which, if that’s all you want, can work. But I can tell you from personal experience: that’s a pretty empty life.

Back in my PUA days, several of my friends and I were very much of the “get laid at all costs” school. Every single one of us hit the wall at speed because you can’t be that manipulative without giving up a big part of your soul. Quite a few had literal breakdowns because of it.


If what you want is meaningless sex, then that’s cool. You do you, my man. But there are a lot of people who think they want it, and the things that they do to get it mean that it comes at a cost.

Am I supposed to be using these uncomfortable Tinder strategies?


Is a dick pump worth anything?

If you’re having a hard time maintaining and achieving an erection and you can’t take Viagra or Cialis, then yes. Otherwise it’s worth about $39 with shipping and handling on Amazon.

Why does my roommate make me feel like these women aren’t really worth much?

Because it sounds like he’s treating these women as though they aren’t really worth much. Maybe he’s convinced himself that he really does have a “connection” with each of them. But all the behavior you’re describing is the behavior of someone who doesn’t give a six-legged rat’s ass about somebody else as long as he gets what he wants.

How the hell is anyone going to be okay with having sex with someone my age with no experience unless they are out just to take my virginity as a trophy?


Now here’s the thing, my dude: you’re way more focused on the “virginity” aspect than the women you date will be. Women don’t date your resume, nor do they date the notches in your bedpost. They date you. They are interested in you as a holistic person.

Being a virgin at your age isn’t common, but it isn’t rare either, nor is it a deal-breaker. I have known many, many women who are in long-term relationships with men who were older virgins. The commonality those men have all shared is that they didn’t make a giant production about being older virgins.


The truth is that your virginity will only be an issue if you make it an issue. If you treat it as some scarlet V or Mark of Caine that women can magically sense, then yes, women will see it as being a problem. Not because being a virgin is bad or a mark that something’s wrong but because you are making a production out of it.

The problem isn’t that you’re a virgin. The problem is that guys who are so hung up on being a virgin that everyone knows about it tend to have a host of other, far more visible issues that women watch out for. Guys who treat it as just one data point about who they are, on the other hand, do much better.


And let me assure you: being a virgin doesn’t mean that you can’t be an incredible lover. Being a great lover isn’t about whatever “tricks” you may have. It’s not about being able to do the Transylvania Twist, the Swirly-Go-Round or the Rusty Venture, it’s about a willingness to listen and a can-do attitude.

When in doubt: alway use your tongue. Communicate, communicate, communicate.

He’s offered to have someone be my “virgin surgeon” to get it over with

… and for some folks, that’s a perfectly legitimate option. If that’s something you’d be ok with, then hey, go for it.

or let me bang one of his ladies.

Ew. On many levels: ew.

I respectfully declined.

Oh thank God.

I just want to understand how any of this is right?

It isn’t.

How it feels as if ‘love’ isn’t a real thing any more? I’m lost and it always seems I have the wrong people helping me.



I get deeply depressed thinking about all these issues and it only further pulls me away from being able to have any confidence to actually finally ask someone out.


Considering that your roommate has specks of good advice buried in a mountain of bullshit, I’d say that this just means that you’re a functional human being…

(Ok so I asked one person out and it ended up not working out since she agreed to go out with me, but then stopped talking to me and went back to her old boyfriend after 3 days).


Don’t read anything into this. A lot of success in dating is entirely based on luck and timing. Sometimes you can meet the right person at the wrong time. Other times, it’s just pure bad luck and there’s nothing to be done. This is the latter.

I don’t know if I’m being silly about this or not. All I know is that I’ve lost hope.

Thank you for reading this long depressing rant. There are other things I can’t currently remember at the moment, but this is a good portion of it. Any help in this matter would be greatly appreciated.

Lonely, Lost Loser

You’re not being silly, L3. You’re a reasonable person dealing with unreasonable ideas. The advice your roommate is giving you is at times borderline sociopathic, and while he may be getting laid, he’s showing you that he can’t keep his partners around for very long.


The fact is that this guy is no role model. I’ve seen plague rats I’d rather take advice from before I took it from this guy. The fact that even thinking of trying to follow his crap is making you miserable should be your first clue that it’s a bad idea. Like I said: if your Spidey-sense is tingling, there’s usually a reason for it. And in this case, it’s that he’s trying to teach you how to treat women like he does, and that’s not you.

I realize that “just be yourself” is the oldest damned cliché when it comes to dating advice, and honestly, it’s bad advice. After all, you’ve presumably been yourself all this time and it hasn’t gotten you anywhere yet. But the right answer isn’t “be someone else”; you aren’t that good of an actor, nor are you sociopathic enough to pull that off. Worse, women aren’t stupid; they can spot a faker a mile off and it’s going to make them flee in the other direction.


You need to be yourself, but you need to be your best self. This doesn’t mean you have to change, it means you have to improve.

Part of your problem is in what you do. Your life thus far isn’t that far off from your roommate’s. While he’s staying home to fuck, you’re staying home to play games. That’s great that you love games, but if that’s all you’re doing… well, there’re women out there who dig that, but they’re few and far between.


Part of what makes you worth dating is that you have a life that potential partners would want to be part of. One of the questions that women ask themselves about men they’re interested in is “what would my life be like if I were dating this guy?” Right now, the answer would be “staying in and playing Tekken.” Which, hey, if that’s what you want from life, more power to you. But how’s that been working out for you so far?

You need to do more than just get up > work > game > repeat. You especially need to do things that actually bring you in contact with women you want to meet and hey, spoiler alert: they’re not in your apartment. (Your roommate’s offers aside.)


The other thing is that you need to take some risks. One of the things I’m picking up from your letter is that you haven’t taken any chances. You’ve had that one woman who went back to her ex-boyfriend, but otherwise nothing. I get that making yourself vulnerable can be terrifying; it can feel like you’re asking to be judged on everything that makes you who you are. But the truth is that there is no reward without risk, and women can’t agree to date you if you never ask in the first place.


Your being a virgin isn’t nearly the dealbreaker that you think it is. You’re investing far more terrible and transformative power in having sex than sex actually has. Fundamentally, having sex isn’t any different than having sushi for the first time or leaping out of a perfectly good airplane. It can be an incredible experience… but it isn’t going to make you into a new person.

When you do have sex for the first time, you’re going to discover that you are exactly the same person you were beforehand. Your dick isn’t going to play the victory theme from Final Fantasy VII, you’re not going to get a new personality download, and you’re not going to turn into Brad Pitt from Fight Club. The only difference will be that you’ll have had a new experience. And you’ll probably need a shower.


You’re a virgin. Cool. This is part of who you are, but it’s not the totality of who you are. You have more to offer than whether or not you’ve had a particular experience yet. Treating this particular milestone as a millstone around your neck is only going to make it harder for you to get beyond it. And here’s a secret: women will almost never ask you for your sexual CV. As long as you don’t have an STI, 99.999% of women aren’t going to care about your sexual history. The number who will care is small to begin with. The number who will ask before you sleep together is so minuscule as to be statistically non-existent. I have been on more dates than I’ve had hot meals and I can tell you: not a single one of them has asked about how many people I’ve slept with.

While there are women who prefer not to date virgins, the truth is that those are women who you aren’t compatible with in the first place. The fact that you’re a virgin tells them one thing about you. Their reaction tells you everything about them.


Now, if you aren’t sure what to do to get to a place where you can ask women out on dates… well, that’s why I’m here. I’ve got years of archives to go through; start with the basics and work outwards from there.

But the thing to keep in mind is that your social success isn’t going to be predicated on lying — either about who you are or about what you have to offer to your potential partners. Your roommate may have a system that works for him, but it comes with a cost. And that cost is clearly far more than you’re willing to pay.


Develop your best self, L3. The more comfortable you become in your own skin, the better you will do. I realize that things can feel intimidating. I realize that they can be scary. Trust me: I’ve been there, done that and printed the t-shirts. But not only are you not hopeless, things aren’t nearly as bad as you believe. I’ve seen people who have less going for them than you go from kissless virginity to incredible marriages.

You have an amazing future in front of you. You just have to take that first step. All will be well. I promise.


Have you ever gotten terrible dating advice from a roommate or friend? Have you worried about telling people you’re a virgin? Share your thoughts and experiences in the comments and we’ll be back in two weeks with more of your letters.

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 on the Dr. NerdLove podcast. His dating guide New Game+: The Geek’s Guide to Love, Sex and Dating is available on 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.