DEAR DR. NERDLOVE: I’ve been a big fan of yours for some time and your advice has helped me through some of my dating misadventures of the last few years.

My current issue is probably not too unfamiliar for your readers. I have a big crush on someone. We were casual acquaintances in college, and about 1.25 years ago I asked her to meet up, knowing that I had some interest in her. We’ve been meeting irregularly and getting to know each other. Recently she has been saying how much she enjoys meeting with me and we’ve picked up our text conversations since the lockdown. I know I want to see those as signs she is interested in me in a romantic fashion, but I also know my mind can make any evidence favorable when properly motivated.

Adding to this is my realization thanks to your advice what one of my biggest stumbling blocks is: I’m boring. I have a very hard time being flirtatious or playful with people I like. I get very anxious about crossing boundaries. I’m not very expressive in my speech in the everyday unless I feel comfortable with someone, and being around my crush is the opposite of comfortable, even though I really like her.

Just trying to find a way to show how I feel and express my attraction and hopefully wring a relationship out of this mess.

Thanks

Tongue Tied

DEAR TONGUE TIED: At the risk of pointing out the obvious TT: you don’t really have a problem here. It sounds to me like your biggest issue is that you’re too caught up in your own head and overthinking things.

One of the mistakes people make is that they tend to assume that there’s only one way to flirt. They see flirting as a specific process, one that looks exactly like, say, George Clooney seducing Jennifer Lopez in Out of Sight or the witty banter of Nick and Nora Charles or the joking style of Will Smith or Ryan Reynolds. In reality, there are as many ways of flirting as there are people. At its core, flirting is simply communicating to somebody that you are attracted to them and like them as more than just a platonic friend. For some people, that means banter and jokes. For others, that means physical touch and connection. For still others, it’s a declaration of interest, telling someone why you like them or how enchanted you are by them.

The way you flirt is going to be as individual as you are, and finding your flirting style simply means finding the way of expressing interest that is most congruent with who you are as a person.

The problem you seem to have is that you don’t believe that your friend could actually like you… all evidence to the contrary. The fact that you met up frequently before the lockdown, that your text conversations have continued since and she’s telling you how much she enjoys seeing you? I mean… I guess she could hire a plane to fly a banner saying “ASK ME OUT, YOU FOOL” over your house if she wanted to be a little more obvious about it, but that might seem a little gauche.

The easiest way to find out if she’s interested is simply ask her out on a date. Now, considering that we’re in the era of social distancing and self-isolation, traditional dates are going to be off the table for a while. But that doesn’t mean that you can’t tell her that you like her, that you’d like to go on a date and see where things go. I recently released a workshop on dating during the COVID-19 pandemic, which you can find over on my YouTube channel. I suggest you check it out; I give a number of ideas for potential dates that you can have via Skype or FaceTime. One date idea that can be fun is to cook a meal together. Set up your laptop or your tablet in the kitchen, open a video chat and the two of you try cooking the same meal… just in your own houses. It’s a way of capturing the feel of preparing a romantic, candlelit dinner together, even if you can’t be there physically. It’s fun, it’s unique and even the potential for mistakes adds to the enjoyment as long as the two of you can laugh it off.

But none of this can happen unless you use your words. They don’t have to be flowery or silly or witty; you just have to make it clear that you like her as more than a friend and want to possibly pursue a relationship. And honestly… I think she’d be very interested in that.

Meanwhile, as a word of advice: part of how you make sure that you don’t cross someone’s boundaries without wracking yourself in anxiety: pay attention to her comfort. If she starts getting uncomfortable, apologize and dial it back. A simple apology and not making the same mistake again will keep you from being a creeper. And if you’re worried that you don’t know whether something is too far — making a flirty or slightly sexual joke, for example — then give her room to decide where the line is. If you metaphorically lean forward 40%, you give her the opportunity to either take it the rest of the way, or to leave things where they are.

Good luck.

DEAR DR. NERDLOVE: Big fan of your work. Really interesting social insights on modern courtship that goes beyond fallacy-riddled generalizations the average internet user is prone to believe and spread around. 

I’m writing this hoping to get some advice from you about this person at work who I’m having a “unique” case of Oneitis on. I say “unique” because all I’m really after is a physical relationship, and not even an exclusive one at that.

Short history; I met her a few years back in a language class I was taking before I entered this new company. She didn’t really stand out then, as she was always tired from work and wasn’t really participating in that class anyway and I was pursuing someone else at the time. That didn’t work out, by the way, and I’m still single up to this day. After that I was surprised to find out we were going into the same company. 

Fast forward a few months later and I was working with her almost everyday. Tried flirting, even spent some after-work time with her and with another friend. After that she was cool enough to clarify that she wasn’t looking for a relationship. That was my first time being active compared to the old style of just hoping fate would hand me a relationship, so I had to deal with the rejection, which in retrospect was not the worst way anyone can reject someone. I got over it, did some introspection, pursued some other interests while still continuing work with her.

That’s when I realized there was little chemistry to make it work as a standard relationship in the first place anyway and I was just intensely curious on what a physical relationship with her would be like because she hits all my major ‘characteristics I’m physically attracted to’. To sum things up bluntly: she makes me really horny. I totally own my desires, even if it all just looks like fodder for the ‘the power of boners are strong’ stereotype. Of course I’m aware this could be something to consult with mental health professionals with but beside wanking off occasionally it’s not getting in the way of work or social interactions. I did stop the flirting after she told me she wasn’t interested and backed off trying to act normal work. Of course, I can’t dismiss the notion I’m only seeing her not as a person, but as someone to be sexual object and that’s just sad for everyone.

What do you think, doc? Is it worth clarifying the relationship I’m interested in or should I let this one go? How do you usually deal with these kinds of desires

Yours truly,

Jalapeño Horndog

DEAR JALAPEÑO HORNDOG: Here’s the thing, JH: if there’s not enough chemistry to make a romantic relationship work, then there’s almost certainly not enough to make a sexual one work. While asexuals and demisexuals certainly exist, it’s a safe assumption that the former is going to come bundled with the latter.

But in this case, there just wasn’t any interest there, period.

If her objection was at having a romantic relationship but she was interested in having a purely physical one with you, she would’ve given you the heads up. “I’m just not looking for a relationship” almost always comes with an unspoken “with you” appended to the end. It’s a softer way of saying that she’s not romantically or sexually attracted to you without being rude or confrontational about it.

Your being attracted to her is perfectly normal. But as I’m often saying: attraction isn’t a commandment. You can be turned on by someone and not do anything about it. You can fantasize about someone all you want, but otherwise you need to let this one go.

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 am not sure how to address this problem and I am hoping that you can offer guidance.

I am a single retired male in my 60s. I live alone and have never been married. I would like to date and I would like to be in a relationship. However, sexually ….. I am not able. No, not even with blue pills.

So my question is at what point in a relationship should I bring up this topic? Certainly not when I am introduced, certainly not after we are married.

I want very much to be in a committed long term romantic relationship. I would feel very uncomfortable getting deep enough into a relationship that sex is about to happen, and then stop and explain and apologize and leave her unsatisfied and confused and probable angry at me.

I don’t know how or when to bring this up. It is stopping me from even trying to find someone and I am here by myself unhappily alone.

Your advice would be appreciated.

Thank you very much.

Lacking Important Marital Possibility

DEAR LACKING IMPORTANT MARITAL POSSIBILITY: Erectile dysfunction can be a motherf

ker, LIMP, not going to lie. One of the toxic tropes about manhood and masculinity is that men are satyrs, ready to bang at the drop of a hat. We’re supposed to be so continually hornt that a strong breeze is enough to get us harder than Chinese trigonometry, ready to go with absolutely no warning. So when you don’t, or can’t, rise to the occasion, it can feel like a direct assault on your identity as a man. It can screw with your sense of self-esteem, your belief in your value as a man and even make you feel as though love, dating and relationships are simply not in the cards.

What we rarely talk about is not just how common erectile dysfunction can be, but how easily it can be triggered. Dicks are like Pavarotti: if things aren’t perfect, they often don’t want to perform as expected, and the things that can affect a person’s erections are vast and varied. Alcohol is the most obvious — damn near everyone has either heard of or experienced the dreaded “whiskey dick” phenomenon before. Stress is another potential boner-killer. So too are issues with blood pressure, weight gain, cigarette smoking, hormone imbalances, prostate issues and a large number of commonly prescribed medications.

In your case, LIMP, if medication like Viagra or Cialis can’t resolve the issue, then it’s likely that you have structural problem. It might be a case of damage to the spongy tissues around the penis, an inability to get sufficient blood flow to cause and maintain an erection, even prostate surgery. This doesn’t necessarily mean that erections are permanently off the table, ranging from using a cock-ring to keep the blood flow from leaving the tissue in your penis to surgical implants — all options that you would have to discuss with a urologist, not a loudmouth with an advice column. However, the fact that you can’t get an erection doesn’t mean that sex and relationships are off the table for you. After all, plenty of folks without penises — men and women — have loving, fulfilling and sexually active relationships… and you can too. Yes, even if erections are physically impossible for you.

The first step is to adjust your ideas around sex. You, like a lot of folks, are equating sex with penetrative intercourse — particularly penis-in-vagina penetration. While this is the most commonly accepted definition of sex, it’s also the most limiting. Sex, especially good sex, is far more about “Insert tab-A into slot-b, repeat”. In fact, penetration is often the least effective way to please a female partner; less than a third of women can reach orgasm through vaginal penetration and 45% of women can’t orgasm from vaginal sex at all. This is no small part of why fewer than 2/3rds of hetero or bi women achieve orgasm via penetrative sex, while 98% of straight, cis-gendered men do. Taking the emphasis off penetration on the other hand, changes the equation entirely; 88% of women who sleep with other women reach orgasm regularly. The difference is that in those encounters, there’s an emphasis on foreplay, deep full kissing, manual stimulation and oral sex… all things that you’re perfectly capable of providing, LIMP. If you’ve got a mouth, hands, a can-do attitude and a willingness to follow directions, you’ve got everything that you need to be an incredible lover for any of the women you ever date.

And penetrative sex isn’t necessarily off the table either. You may not be able to achieve penetration with your biological penis, LIMP, but there are plenty of substitutes out there that you can employ instead. Sex toys — starting with simple vibrators and dildos — can provide the penetrative sex that your partner may want. And if you both want that old-school sensation of body-to-body thrusting, there’re harnesses designed for men that let you situate a strap-on toy over your groin; put that sucker on and you don’t just have a cock that’ll never go soft on you, you can custom-fit it to the needs of the evening. Does your partner want something long and girthy for that “incredibly full sensation”? Those are available. Does she want something designed to stimulate her clitoris during penetration? Those are ready and waiting for you. Hell, you can even get crazy, non-human toys from companies like Bad Dragon in case you and your lady friend feel like getting a little freaky.

Nor does your inability to achieve erection mean that YOU can’t have orgasms either. Digital stimulation of the prostate gland — whether with a well-lubed finger or a prostate massager — can help you reach orgasm and ejaculation, even if you can’t physically have an erection. Plus, there are toys like the Pulse Solo or Duo, which are designed to be used with a flaccid penis; they use vibrations to stimulate the frenulum on the underside of the penis. The Duo even comes with a remote control, allowing your partner to be directly involved with your orgasm.

And while we’ve focused on how sex isn’t an impossibility for you, there are people who have romantic relationships without sex. Many people, especially older couples, have companionate marriages; their relationships are about love and companionship and emotional intimacy, but don’t have a sexual connection. These are a perfectly valid and satisfactory relationship model for more people than you’d realize. They might have an open marriage, where one or both parties are allowed to seek outside sex partners, or one or both partners may fall on the asexual spectrum and simply aren’t interested in sex. Asexual women do exist, after all, and many of them despair of finding love, companionship and marriage because they don’t want or like sex.

But regardless of the options that work best for you and your needs, none of this can happen without your using your words first. You’re going to need to be willing to talk with your potential partners about what you do and don’t have to offer, what you need and what you can provide them. The ideal time is going to depend on the relationship and the person involved. This isn’t a conversation that I would roll out on the first date, but it’s not one I would necessarily hesitate on. My rule of thumb would be that you would want to have a couple of dates first before bringing up the subject. This gives you and your date an opportunity to get to know each other, decide if you have sufficient chemistry and interest and, importantly, decide if this is a relationship you even want to pursue in the first place.

If you both decide this is something you’d want to pursue, that’s when you have The Awkward Conversation. Schedule a time for the two of you to get together in person, when you won’t be interrupted, then sit down and explain your situation in a calm and matter-of-fact manner. Tell her exactly what’s going on — you’re not capable of having erections — but also what you can do, the kinds of sex you can have and enjoy having. Then give her a chance to share her side. Let her ask questions, share what her needs, must-haves and boundaries are… then move forward from there.

What you don’t want to do is roll this out as though you were broken or to treat this as something shameful or a deep dark secret. The fact that you can’t have erections isn’t something to be embarrassed about, nor is it the totality of who you are as a person. It’s just a single fact, a datum in the constellation of you as a hollistic man. If any potential partner finds that one thing about you to be a dealbreaker, then all that’s happened is that she’s proven to be someone who simply isn’t right for you. She’s self-selected out of your dating pool and now you’re free to find someone who is a good match for you.

Oh, and one more thing, LIMP: I think it might not be a bad idea for you to seek out an escort or sexual surrogate. Visiting a sex worker or surrogate who are experienced in non-penetrative sex can help you get in touch with the kinds of sexual experiences that you enjoy and would want to have with your future partner. Having a good understanding of what you want or enjoy makes it easier to share your needs with the women you want to date. Being able to walk them through what sex with you would look like from a position of experience can help make that conversation easier. It’s a little less intimidating if your partner can say “here’s exactly how we can do X, Y or Z” instead of worrying that you’re going to have to try to make it up as you go.

I realize it can feel overwhelming or hopeless, but you have far more options and opportunities than you realize. There are some amazing adventures and relationships waiting for you, LIMP; all you have to do is reach out for them.

You’ve got this.

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 looking for advice because although I’m not 40 years old, I will be next year and I’m dealing with a problem I’ve been avoiding most of my life and I’m starting to realize that if I don’t address it now I will be alone forever.

The actual status of being a virgin doesn’t bother me so much as not being able to get started. I’ve somehow gone 39 years on this planet not being able to form a single relationship with another woman. I’ve never been on a date in my life, I’ve faced rejection all my life and sometime in my early 30’s, I just stopped. I wish I could adhere to the “Never give up” philosophy but the truth is that after a lifetime of failures and not a single success to latch onto, I don’t know any other way and I just stopped. I’m tired of being rejected, of being unwanted, dating and relationships became something other people did and I need not concern myself with it.

Now as I’m approaching my 40’s I’m facing the problem of loneliness and not being able to take action when I think I might actually have a shot with someone.

I’ve been crushing hard on a female friend and I don’t know how to handle it. She confides in me, she inspires me and I’m fairly certain she wants me to make a move on her but I just can’t. I’m quiet and mostly keep to myself but she approaches me and even offers to drive me home sometimes and isn’t repulsed if I ask for a hug. I’m confident at least that she likes me as a friend but I’m paralyzed with doubt and fear. I’ve told myself for 2 years this is just some infatuation, I’m crushing on a woman because someone finally started giving me attention and is being friendly and I’m being ridiculous. I tried to wait it out and let the feelings die like these intense feelings usually do, but this isn’t going away and she opens up more and more about her struggles to connect with people and start a relationship due to only being in 1 LTR in her life, if only she knew……

The more I think about it, the more I convince myself to just say something and ask her out or tell her how I feel, the more I realize that I’m just scared. I’m scared of rejection, I’m scared of her getting a boyfriend and yet would feel relief if that happened. But mostly, I think I’m scared she will say yes. Then I will have to spend time with someone and it’s all uncharted territory. I’ve never dated before at all. I went to some bars and clubs in my early 20s with friends and it was among the worst experiences in my life. I’m not social and she is among the few friends I have. I don’t know where to go, what to say, what to wear, what to do, and most of all, just being vulnerable and opening up to someone is terrifying. The anxiety is overwhelming and I find the best recourse is just to avoid her until I’ve cooled down and I’m almost certain if she has feelings for me she must feel awful if I’m never acting on them.

So yeah, whatever advice you can give, I’d love to hear it. All I know is that I have to do something soon because if I don’t, nothing will ever change.

Untouched at 40

DEAR UNTOUCHED AT 40: I suspect the biggest issue you have is one of deservedness, Ua40. A lot of folks, especially late bloomers like yourself, tend to have a hard time in believing that they’re someone who deserves a relationship. The logic — such as it is — tends to be an assumption that if they were worthy of a woman’s time, attention and affection, it would’ve happened by now. Since it hasn’t… well, it must be a sign that there’s something wrong with them.

In reality though, it’s nothing of the sort. More often than not, the thing that holds people back is fear. Not just fear of rejection — which feels obvious — but also fear of success. It sounds absurd; why would someone be afraid of getting what they want? But the thing is: as long as something is only a fantasy or only potential, then you can’t screw it up. A fantasy can be as perfect as you want it to be. Potential means that it could be EVERYTHING and ANYTHING; making it real means that you might make mistakes and have it all fall apart on you.

This is in no small part why some guys end up with crushes on people that either they never ask out on a date or who they know to be unavailable; it’s easier to stick with the known, even when it’s painful, than to try to live up to your fantasies or ambitions.

At the same time, that lack of deservedness can cause you to end up with crushes on people for the wrong reasons. When you feel like nobody could possibly like you or that you’re not “worthy” of love, sex or relationships, it’s incredibly easy to latch onto anyone who shows you a little affection or interest. It becomes almost a recipe for heartbreak because you crave something so badly that the hint of it makes you overlook issues like basic compatibility or mistake platonic affection for romantic affection.

And y’know, I get it, especially the sense of knowing nothing but rejection. That can be incredibly disheartening. And while my general philosophy of rejection is that many — if not most — of the time, rejection has nothing to do with you as a person, sometimes that rejection is a sign that it’s time to do things differently. If you’ve been approaching meeting women and dating the same way and getting the same results… well, sometimes that means you have to take a look at your approach, at all the commonalities and decide to make changes.

Now for you, part of what I would suggest would be to find a counselor or therapist. The fear and anxiety you have is the sort of thing that’s best handled by talking things out with a trained professional, not just a loudmouth with an advice column. But another part of what I would suggest is being willing to go back to first principles and work on not just yourself but your perception of yourself. Who you are as a person doesn’t necessarily need to change, but how you see yourself does. Many times, the reason why guys struggle with dating isn’t because they lack the skill or the courage to date but because they don’t let themselves do what they’re truly capable of.

Part of what people think works about things like pick-up artists or The Red Pill or other systems that teach you how to date and meet women isn’t inherent to the system. It’s not that, for example, Mystery’s advice to dress weird was making people more attractive or that using pre-scripted material made you a more interesting person. What it was almost always doing was forcing you out of your comfort zone and into doing things that you might never otherwise do. Peacocking didn’t make you more attractive, it forced you to think differently about how you dress and to try things that would otherwise be “out of character” for you. Canned material didn’t substitute for a personality, it just gave you the feeling that you could talk to women. Even bulls

t ideas like negging or attitudes about “being alpha” were functionally about getting you to behave differently than you would otherwise.

In a very real way, a lot of pick-up et. al. was the sociological equivalent of Dumbo’s magic feather; it didn’t actually work, it just gave you permission to do things differently and finally discover your true capabilities.

Now here’s the thing: feeling like you have that permission and those capabilities will actually ease your anxiety. Feeling capable, feeling like you have the capacity and ability to succeed gives you a sense of control and agency, which in turn, helps give you a sense of certainty. Part of why you’re so anxious around your crush is because of the ambiguity of the situation; she’s both potential love and potential rejection. Being unable to resolve that sense of “what if” is what’s preying on your mind and on your calm. Getting an answer one way or another — even if it’s a “no” — would end the ambiguity and chaos and give you certainty. A “no, thank you” wouldn’t be the result you would hope for… but it would mean that you would have an answer and you’d be able to move forward.

And honestly, the longer you let situations like this go on, the more anxiety-producing they become. The more time goes by, the more you are invested in the outcome, which means that you’re also making yourself more afraid of a potential “no”.  And now you’re stuck between the fear of success, the fear of rejection and the anxiety of the uncertainty between the two.

So while I strongly suggest that you find a counselor to talk out some of your issues, I think it’s also time to start resolving to act out of character and force yourself out of your comfort zone, so you can finally unlock your true potential.

Part of that would be to take inventory and ask yourself: in an ideal world, what would you be like? How would you act, how would you dress, how would you feel about yourself? Then, as you list these qualities, start to brainstorm ways that you can incorporate them into your life now, instead of waiting for the day when you’re “allowed” to feel, dress or act that way. The more you work to manifest your ideal self now, the more you begin the transformation that will help you change your life for the better.

Another, and possibly more crucial part of making that change will be to internalize one of the lessons that Carrie Fisher left us with: “be afraid… but do it anyway”. It’s ok to be scared or to be afraid of rejection. But the truth of the matter is that the fear of rejection is more painful and more debilitating than the rejection itself. Risking rejection right away lessens the impact it has on you because you haven’t given it time to build and build until it becomes a giant monolithic entity that always lurks in the back of your mind.

And when it has already become this monster in your life? Then the key is to finally face it and get your resolution, so that the ambiguity doesn’t prey upon you the way that it does now. Even being told “no” is better than letting the fear build. While being rejected may hurt, getting that no and facing that pain will do two things.

First: you’ll realize that rejection may suck, but it won’t kill you. You WILL survive it.

Second: by getting rejected, you’ll finally be able to start to heal and move forward.

Resolving that ambiguity will mean that you won’t feel as anxious around your friend because you will finally have an answer. And if that answer is “no”, then you’ll finally be able to heal and move forward with your head held high because you had the guts to do the thing that terrified you. There is honor in that, and you will know more of what you’re truly capable of accomplishing.

That’s why asking your friend out on a date would be a start to transforming yourself into the man you can be. Tell her this:  “Hey, I really enjoy hanging out with you and talking with you and I love our friendship. But I’d also like to take you out on an actual date and see if there’s something more there. If you’re not interested, it’s totally cool to say so; I’m just as happy being your friend.”

You will stammer. You’ll feel your heart pound. But just by asking her, you will have started the process that will transform you. Simply asking the question — a seemingly tiny gesture — is your first step towards a better life. You will have proven that you can do things differently and challenged your limitations. Whether the answer is yes or no, you will have forced yourself outside of your self-imposed limits and put yourself on the path to make your life better. Because you’re right: you need to do things differently, or nothing will ever change.

And even if you crash and burn… well, the phoenix has to burn before it can soar as its true self.

You are untapped potential, Ua40. You are braver than you give yourself credit for, you’re stronger than you know and you’re capable of far more than you’ve ever believed. You just have to reach for it.

It’s time to let go of your earthly tethers and fly.

You can win if you dare.

Good luck.

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