DEAR DR. NERDLOVE: I am a 21 year old girl with severe self esteem issues. I have a full face that is extremely plain and my smile is hideous. My hair is nice, except for the color, it’s a clingy orange/yellow color. I can’t bear to look in the mirror or see pictures. I almost cry every day. So now that you know a little bit about me, here’s my problem.

For the past three months, a really good friend of about 3 years and I have started texting regularly. And texting a lot…. first thing in the morning and sometimes all the way to night. I’ve liked him for a while – he does not know this. Sometimes I feel like he is flirting with me but I don’t know. I refuse to admit he likes me because why would he? I am not attractive and I don’t really have anything going for me. I need to tell him I like him, I can’t be just friends anymore. I have what I’m going to say all worked out.

But I don’t know if I can bring myself to do it. I don’t think he could ever like someone who looks like me…..

What should I do?

Too Much To Hope For

DEAR TOO MUCH TO HOPE FOR: If I’m being honest, TMTHF, I think your first step should be talking to a counselor. I fully acknowledge that’s something I say a lot around here, but there’s only so much a loudmouth with an advice column can do — especially, as I’m always saying: Dr. NerdLove is NOT a real doctor. If you literally can’t stand to look in the mirror and you’re crying every single day… that’s honestly the issue you should focus on. Even if we’re strictly cold-blooded about this, the ratio of effort-to-outcome and the knock-on effects of dealing with your feelings of low self-esteem and emotional despair far outweigh telling your crush that you’re into him.

I mean, pretty much everything about how you describe yourself and your feelings in your letter screams depression to me. But even if it’s not, having a professional to help you unpack these feelings, pick them apart and figure out ways of addressing them is going to do you a world of good. And if you’re currently a college or university student — and your age certainly makes that more likely — you have the advantage of having your school’s health center and attendant resources. That makes it a lot easier (and cheaper!) to find a counselor than if you have to start from scratch or with a referral from your GP.

Now as for your friend… sometimes you have to be willing to accept “yes” as, if not an answer, than at least a possibility. As I’ve told ROTFML and many, many others: just because you feel a particular way, especially about yourself, that doesn’t mean that it’s true, or even accurate. You are convinced that you’re plain with a hideous smile and weird not-quite-ginger hair. That doesn’t mean that’s the case, nor does it mean that people don’t or couldn’t find you attractive. It’s more about letting yourself believe it, especially when an opportunity drops into your lap and starts to wiggle.

Is he into you? Is he flirting? Would he respond positively if you told him you have a crush on him? I couldn’t say. What I can say is that, as a general rule, people don’t text all day, every day, from dawn until dusk, with folks they don’t like. Maybe you and he are just really tight friends with a strong connection. Or maybe he’s caught some feels. After all, science has found that people become more attractive to us as we get to know them better. It’s certainly well within the realm of possibility.

Now, my personal philosophy is that I’m not a huge fan of declarations of feelings… not, at least, in isolation. While it makes for great dramatic moments in shoujo manga or CW shows, I find that in practice, it tends to come across as “Here are my feelings, now you need to do something with them.” That can often put a lot of pressure on someone to decide right then and there what kind of relationship they want to have, possibly before they’ve thought beyond “Well, I’m interested in trying something with them.” I’ve found that what works better is to ask someone on a date — not to hang out,  not to get together some time, but a proper date. This tends to be a much easier ask; all they’re agreeing to is an evening, not to try to figure out the entire relationship. Plus: the romantic and/or sexual interest is implied; people don’t generally ask folks they don’t like out on dates.

There’re a lot of ways to frame this, especially considering you and he have been friends for a while. Personally, I prefer to do what’s known as “inviting the ‘no'”. That is: you make it clear when you ask them out on a date that it’s totally ok for them to say “no, thank you”. This helps dial back both the potential “feelings out of nowhere, what do I do??” overflow error and the fear that saying anything other than yes would ruin the friendship or make things awkward. So in your case, what you could do is say “Look, maybe I’m completely misreading things but I feel like there’s kind of a flirty vibe going on between us and I’m into it. I really like our friendship and what we have and I would never want to lose that, but I’m interested in seeing if maybe there’s more. It’s totally ok if the answer is no, but would you be interested in going on a date and seeing how things go? If not, that’s totally ok, and maybe it’ll be a bit awkward for a little but we can resolve to power through the awkward. What do you think?”

And then the ball’s in his court.

But, regardless of whether he is interested in you or not, I think one thing you don’t have to worry about as much is ruining what you have now. A long-standing friendship that seems to have gotten closer and more intense is generally not the sort of thing that falls apart after one speedbump (or, in this case, one invitation on a date). I also think that the risks of not asking him mean living with the pain of uncertainty, ambiguity and wondering “what if”. Getting an answer, even if the answer is no — and I’m definitely not saying that it would be — is almost always better.

But seriously. Prioritize talking to a counselor above everything else. You deserve to feel better about yourself and to treat yourself better than you are right now.

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 a 46 year old man and, for no obvious reason, I’ve never had sex. I’ve made out with three women my entire life. I’ve pretty much given up trying to lose it at this point.

Whenever I tell women I’ve never had a relationship, they don’t return my calls. I’ve only told a couple of girls I’m a virgin, and they both glared at me like I was a circus freak. I don’t really know what to do anymore. I feel like I blew it. I don’t really think I can lose it anymore, I just wanna reconcile this so I can sleep at night. How can I accept this and move on?

Resigned, Regretful and Rueful

DEAR RESIGNED, REGRETFUL AND RUEFUL: So, a couple of things R3.

First and foremost: I can all but guarantee that you’re not getting the reactions you think you’re getting — and certainly not for the reasons you think. I am more than willing to wager the price of a double cheeseburger and fries that your jerk-brain is ramping up people’s reactions into ball-shrinking scorn. In fact, I’m willing to further wager the addition of a milkshake that the single biggest reason you get these negative reactions is because of the way you roll this information out about yourself to the women you’re talking to.

I mean, my dude. I can feel the despair and self-loathing radiating from your letter. It’s like Eeyore took a vacation to Pripyat before trying to chase Rick Jones off a gloom-ray test-site. If you rolled out any of this to them the way you did to me? Yeah, I can understand why people might feel a little weird around you. Even folks who are down to clown are going to be a bit put off by someone saying “it’s ok if you don’t want to f--k me. Nobody does. I wouldn’t f--k me either.” You don’t need to go around proclaiming that you’re the hottest s--t jumping out of the coffee pot, don’t get me wrong, but there’s a reason why advertising firms don’t sell products with “look, nobody else likes it but maybe you will.”

It’s one thing to be a virgin, even an older virgin. That’s not an indication of your value or your worth or anything other than “I’ve not had this particular experience”. It’s another entirely if you’re talking to people you’re attracted to and telling them that “oh by the way, nobody likes me and it’s probably because there’s some horrible flaw that women can smell on me”. All that does is signal a host of negativity that most folks simply aren’t going to want to deal with. Even someone who’s absolutely determined to climb you like a tree is going to have second thoughts.

But just as importantly, that negativity and despair that’s coming across in your letter utterly f--ks with how you see the world. As I’ve said many times before: your attitude is the filter through which you view the world. Not only does it affect your ability to perform and your ability to succeed, it also changes how you interpret the world around you. When you believe that there’s some inherent deficiency in you that others find appalling, your brain is going to interpret everything in that light. Polite laughter becomes mockery. Confused looks become glares. Even momentary discomfort or awkwardness becomes “glaring at you like a disease”

And that’s without any possibility of having brought it up at an inopportune or inappropriate time. That’s always going to be a factor as well.

And here’s the thing: as with a lot of folks who lament being “too old” to be a virgin… you could lose your virginity tomorrow if you wanted. Sex work is a thing. Escorts exist, including escorts who cheerfully take older virgins as clients. Even if you were worried about the legality or ethics of it, legal sex work exists too. Flights to Reno are cheap and the legal brothels will even send a car to pick you up at your hotel or even the airport. But the issue isn’t your virginity… not really. The issue is in your head and heart; it’s the way you feel about yourself and the way you clearly feel that being an older virgin is a mark of shame. Even if you were to find someone tonight who was going to ride you like a bronco in the rodeo… there’s still going to be that part of your jerkbrain that’s going to whisper “that didn’t count”. Because there will always be some reason why it didn’t count; it was a pity f--k, you paid for it and she would never have slept with you otherwise, she wasn’t having sex with you so much as using you for something… there will always be an excuse.

While I certainly don’t think that it would hurt for you to get your ashes hauled — professionally or otherwise — I think what you need more than sex is therapy. Not because you’re broken or flawed, but because you’re clearly carrying around a lot of pain and emotional turmoil and no amount of f--king is going to cure that for you. If you were to go out tonight, find the woman of your dreams and bang like a screen door in a hurricane, when you woke up the next day, you’d realize you’re the same person you always were. Again, not because there’s something wrong with you but because sex isn’t magic. It’s not transformative. It doesn’t change you on some fundamental level. Losing your virginity no more alters who you are than eating shawarma for the first time.

The problem isn’t your lack of relationships with others, it’s your relationship with yourself. You don’t need to reconcile being a virgin, you need to heal your heart and your mind. And the only thing that’s gonna do that is talking to a counselor or therapist.

My suggestion would be to visit the Association of American Sex Educators, Counselors and Therapists’ referral directory and find a counselor in your area. If that seems too much, or you can’t find one, you may want to consider an app like BetterHelp or TalkSpace; those can also put you in contact with licensed, professional therapists. But regardless of how you find one… that’s going to be the first and most important step. The sooner you start, the sooner you’ll find that your life is far, far better than you realized and you have more hope than you ever allowed yourself to believe.

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: This is my first time actually writing something like this, but I’ll do my best: 

I am a 20 years old woman, just turned 20 actually, and haven’t really dated any one or had sex or even kissed or held hands, or hugged a significant other. I don’t think it’s weird. My problem is, I know what I want in life and I’ve done a lot of research on how to talk to or meet potential SO, but never really executed them. 

When I watch shows, I even write down tips on how to flirt with people, but that never goes anywhere either. I don’t have much confidence in myself (possibly because I also call myself a raccoon, but that’s besides the point) I have less confidence when it comes to my approaching someone, but I fear if I don’t, no one would approach. 

I know I’m not cute, maybe a little on the unattractive side, I know that, but I try everything else to make up for that fact. 

Look, honestly, I don’t feel my situation is unique and I don’t think it is, but I desperately need some advice on what I should do to get more confidence in talking? 

Wallflower

DEAR WALLFLOWER: Here’s the thing about social skills, Wallflower: they’re skills. They’re not innate; they’re something that you can improve with deliberate practice. But you have to actually practice them. I know a lot of folks who can tell you all about how much studying they do, how much research they’ve accomplished, how many books they’ve read or even courses and seminars they’ve attended… but they’re still stuck. And the reason for that is because all the studying and theory in the world isn’t a substitute for actual boots-on-the-ground experience. You can take all the notes you want on how folks flirt on TV or in movies — God knows I reference plenty of them as examples — but none of that matters if you don’t put them to work.

That’s why you can’t study or theorize your way to confidence. Confidence is built through experience. Confidence isn’t about succeeding or knowing you can’t fail, it’s knowing that doing something won’t destroy you. Fear + survival = confidence, and that only comes from real-world application.

Now that being said, this doesn’t mean that you need to go out and start hitting on folks for practice. The great thing about social skills is that you can practice them in low-stakes, low-investment environments. At 20, you’re in a good position to actually practice being social. If you’re going to college or university, there’re an almost infinite number of opportunities for you to go to events or gatherings and just work on talking to people. Not to hit on them or flirt or find a partner, but to just talk, without an agenda. If you go with the mindset that you’re just practicing, that you’re only out to meet people and enjoy yourself, then it’s much easier. By not being attached to a particular outcome, you’re better able to relax and just be in the moment, instead of weighing every word that comes out of your mouth or the nuance of every gesture or intonation from other folks. All you’re doing is talking.

The more practice you get in just talking with people and joking with people, especially when it doesn’t “count”,  the better you’ll do when you’re in a place where you do want to flirt and joke and maybe see if someone wants to grab a coffee somewhere. The same skills you apply to joke and make friends are the same skills that ultimately help you find a significant other.

Even if you’re not going to college, you have opportunities to practice your social skills. A public-facing job — whether its in sales, customer service, even service industry jobs — means that you’ll have to talk to many, many people from all walks of life. It’s very hard to not become more socially fluent and at ease in those cases. You’re literally required to talk to people and put in the proverbial 10,000 hours of practice.

However, one thing you should definitely stop doing, even if you do nothing else, is talking yourself down. I get the impulse to insult yourself or make fun of yourself before anyone else can; God knows I’ve done it enough in my time. However, constantly insulting yourself, saying that you’re unattractive or that you’re a raccoon or what-have-you affects your self-image. Even if you’re only doing it jokingly, when you say and think things often enough, you train your brain to accept them as true. Self-deprecating humor quickly goes from being jokey-jokes to how you actually feel about yourself and how you expect others to treat you. Learning to love yourself, even hype yourself up is important, and it goes a long, long way towards helping you build up your confidence and self-esteem.

Good luck.

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