Ask Dr. Nerdlove by Harris O'Malley

How Do I Ask My Crush For A Date?

DEAR DR. NERDLOVE: I am pretty young at 18 years old still in high-school during my senior year. I think I look pretty good in the face, but I am very skinny for a guy of my height of 6’4. To give a image, if I was any skinner I would probably look like one of those starved POWs in those war crime pictures in history books. I am not anorexic, but I am afraid that whenever I get intimate with a girl she will go “ew”. I haven’t had a problem with that with any of my exes, but I don’t know what they really thought in their minds…

Anyway enough about me and to the meat of my problem. Senior ball is in February of next year near Valentines Day. I missed my junior prom due to my most recent ex breaking up with me a few weeks before it. This girl I am talking to right now is a really sweet person, but I don’t know how to connect with her. Well I have known her for a year, she has flirted with me before but I never really got around to asking her out since I usually dated someone, or she dated someone. We aren’t close friends in the same social circle.

Well I decided to ask her out early in the year to senior ball, so I wouldn’t have to stress over it when the time approaches, and because I want to date her. Well she did agree to go with me. Everything seems fine right? Well no, because just because she agreed to do that doesn’t me we are dating yet. I am planning on asking her out pretty soon, but there is a problem…..How do I know she likes me enough to date me?

I am a pretty shy person doc, and you have probably heard this before, but it seems like there are FEW girls in my area that share my interest….and that are decent looking. How many girls do you know that live in rural south that collect Warhammer 40,000 miniatures, while reading every 40k book that comes out? Not many, and while I don’t need a GF that likes 40k, I just can’t really relate to many of them besides personality.

So in the recent days I have been texting her, and one time we were in a middle of a conversation about animals since she is a avid animal lover, and she just stops texting back. Granted it was late at night so she could have just fallen asleep, but its been a day since then and she hasn’t replied back even though she has been online recently. I just feel like she’s not attracted to me enough for a real relationship, and I really don’t want to go to the ball or prom alone this year, so I don’t want to push too hard too early and ruin that chance. When we talk in person it just seems awkward, probably because I am slightly nervous. There aren’t many people I am interested in, and the few that I am are either taken, or I have no idea how to approach them.

I can’t make a move, I can’t think of what to do next, and I sure as hell can’t flirt. I don’t know what to do Doc.


No Game No Life

DEAR NO GAME NO LIFE: First of all, NGNL, do yourself a favor and do an image search for Sid Vicious. Notice that he’s heroin-addict skinny? (Understandably, seeing as he was a heroin addict…) That didn’t stop him from being sex on legs to a very large audience. There are a lot of women who love them some tall, lanky guys, just as there’re women who dig them some bears or otters or just about every other body type under the sun. By all means, eat healthy and exercise so your hip bones aren’t going to poke somebody’s eye out, but don’t stress the skinny, especially since, y’know, you haven’t actually had that problem.

Besides, if a woman wants to sleep with you, by the time the shirt comes off, it’s pretty much fait accompli anyway. They’ve already got a pretty good idea of what to expect.

But let’s get to your question, NGNL. You’re pretty deep into reading the tea leaves and looking for answers and that’s not going to help you. There’re all kinds of plausible, even likely reasons why she dropped off the conversation and hasn’t been responding, most of which have nothing to do with you. If you spend too much time trying to what-if your way into her head, you’ll drive yourself insane.

But there’s a simpler answer. Here’s the DNL all-purpose guide on how you find out if someone’s interested in you: you grab yourself by the balls or the ovaries, depending and ask them out. While women can and do give a number of signals about whether they’re interested or not, the longer you wait and try to read the tea leaves, the harder it gets to just pull the damn trigger. The question starts to loom larger between the two of you, making you feel awkward and nervous because you don’t want to throw away your shot but you don’t know. Meanwhile, the longer you wait, the greater the chances that someone else will ask her out first and – well, she may like you, but you’ve never given her any real sign that you like her that way, y’know?

So ask her out. Either she says yes, and blessings on you both, or she says no and now you don’t have to ask whether the cat in the box is alive or dead. You’ve gotten your answer and now you can move on with your life instead of being stuck in this perpetual state of “Well maybe” and “What if”.

And on a personal note: trust me when I say that prom’s fucking overrated. If I knew then what I know now, I would’ve skipped most of my school dances and gone and played Lazer Tag with my friends instead. Would’ve had way more fun too.

Good luck.

DEAR DR. NERDLOVE: I am a thirty-five year old male virgin, and I have no idea how to go about changing that. Looks-wise, I think I’m fairly average — pudgy without being significantly overweight, anyway. My main problems are inside my own head. I’ve struggled my entire life with depression, anxiety, low feelings of self-worth, and difficulty with making human connections. I know all that indicates I should work on myself first, and that having major relationships would be more likely to fuck me up more than anything… but I’ve been trying to do that my entire adult life, and I haven’t gotten nowhere. So I don’t know what to do with myself.

(Before you ask — no, I’m not an incel. I own my shit. I know better than to blame my failings on women being choosy or conspiracies or evolutionary biology or feminism or whatever. The root cause of my problems is me. And I refuse to put the onus for that on anyone or anything else just to salvage my own ego.)

Anyway, let me try and get to the point here. It’s hard to pair down an entire lifetime of issues into just a few questions, but here’s my best attempt:

– How do I overcome my insecurities about my lack of experience with love and relationships for my age? Is there still hope for me at this point?

– Is there any way for me to get where I want to go without pretending to be someone I’m not?

– How do I avoid sabotaging myself? I have a long history of only developing attractions to women who are clearly out of my league. Any advice on how to stop doing that, and how to stop my brain from nitpicking or expecting a perfect match?

Big questions without any easy answers, I know. But that’s where I am right now. That’s where it feels like I’ve always been.

Thank you for your time.


Lost, Alone, and Frustrated

DEAR LOST, ALONE, AND FRUSTRATED: The first thing I want you to do is go back and read my response to Volcanic Sacrifice on 10/17, because many of your issues overlap. I want you to pay attention to how the many of the answers you are looking for can be found by addressing the core anxieties surrounding the way that you’ve adopted “OLD VIRGIN” as an identity. Like I told Volcanic Sacrifice: the fact that you’re a virgin doesn’t say anything about you as person. Your virginity isn’t the source of your problems; if anything, it’s a symptom of a lifetime of dealing with anxiety and depression. It has nothing to do with your worth as a person, it’s a side-effect of your struggles to love yourself and to connect with others. I also want to drive this home: you’re not alone; I’ve known virgins of all ages and all over the gender spectrum; straight, gay and bi, cis and trans. And you know what? There has been hope for every single one of them.

And there’s hope for you too.

The first thing that I would suggest is that you read the excellent article “Embracing Newbiehood: How to Approach Dating and Sex in Your 20s With Little or No Experience” by Cass Bell over at Scarletteen; they have a lot to say that’s relevant to you. One part that I think is especially relevant to you is that you don’t want your being a newbie — or feeling like you’re “behind” — to push you towards relationships where you don’t bring your whole, authentic identity to the table. Your being a virgin isn’t something that you need to hide or be ashamed of; it’s simply one part of who you are, and not even an important part. But if you’re approaching relationships as though it’s something that you need to hide, then you’re going to be coming to them from a place of fear and anxiety; you’re always going to be waiting for that sword to fall, and I can tell you from experience: that’s no way to go through a relationship.

Similarly, you’re allowed to be discerning in who you choose to date or what relationships you choose to pursue. Some folks — especially guys — will pursue toxic or even abusive relationships solely because they feel like that’s “all” they can have; it’s their “best” or “only” chance to lose their virginity, so they’ll grin and bear it and suffer through it because they think they have no other options.

Other folks — like you — will chase after inappropriate partners, people who are ultimately unavailable because they’re unavailable. It’s not that they represent an impossibly high standard so much as that they represent guaranteed rejection. People who take this path do so because they feel like they don’t deserve happiness, and so they kneecap their own chances before anything could possibly happen.

And while I’m on the record as saying that you don’t necessarily have to tell people that you’re a virgin… I think it’s far better if you do. It takes a lot of courage and strength to be vulnerable to others, but in doing so, you’re living your authentic and genuine truth. That’s important, both in what it tells others… and what it tells you. It lets others know who you are and filters out people who are clearly wrong for you. But by the same token, it reminds you that there’s absolutely nothing wrong with being a virgin. You have nothing to be ashamed of LAF; you haven’t done anything wrong, you’re not deficient, you’re not broken and you’re not lesser than someone who has had sex.

I think you would do well to think of yourself less as a virgin and more as a newbie. You’re not deficient, you’re simply new to sex and sexuality and that’s fine. You have just as much of a right to discernment, to have and maintain boundaries, to advocate for your own needs and pleasure as someone who’s had one partner, ten partners or a hundred partners.

And like I’ve told many other folks who’ve been in your position: if you decide you want to just get it out of the way, then that’s cool; that’s as equally a valid choice as wanting to lose your virginity in the context of a long-term, committed relationship. But however you decide you want your first time to go, make sure it’s with a partner who’s compassionate, caring and giving — someone who’s invested in your experience and who’s willing to listen to you.

Good luck.

Please send your questions to Dr. NerdLove at his website (; or to his email,