DEAR DR. NERDLOVE: I’m sure you get messages like this all the time, but I’m at a point where I feel like nothing will get better for me. I’ve always felt like a social reject, although I don’t struggle with socializing or making friends, I do struggle with relationships & sex. I’ve always had low self-esteem and a firm belief that I was unworthy, and too ugly for intimacy. I was made fun of for being an introvert, soft-spoken and also my ethnicity. This caused me to lack confidence growing up. I had hoped to deal with all this by the time high school ended, but things just got worse. My college experience was mentally depleting too, I went to parties, but never had sex. At this point, I knew I was abnormal. It kind of confirmed my worst fears that I’m undesirable, and nothing would change. I’m not particularly hot, but I have always had a muscular build (played rugby), and I assumed that I’d eventually stumble into something. Maybe I took rom-coms too seriously, I don’t know.

I did have a relationship at 26, going on 27. I had some performance anxiety issues, and felt so humiliated. My partner was supportive, but I still felt emasculated, like a failure. I was able to please her consistently, and make her cum through fingering and oral. Although I was hard at times, I just was too nervous for intercourse. I still feel like a “virgin,” and beat myself up for not being better. Notably, this woman had some trauma from sexual assault, so intimacy was difficult. She was kind of stiff and uncommunicative in bed, and I am glad that I was able to give her pleasure. I experienced a genuine connection with her, but am deeply dissatisfied. Part of me fears I’ll be a punchline with her friends and future partners (“limp dick loser” etc..).

The relationship ended because she felt I was too distant (in terms of location and mentally). My first meaningful relationship with a woman ended without intercourse, which is something I dwell on everyday. To clarify, she never made fun of me, and said affirmative things about me I’d thought I would never hear. Sex is a two-way street, and she had clearly been through a lot. I’m glad I could provide her some comfort, but I did not enjoy myself. I’m rambling, but I don’t struggle to get an erection, I just rarely feel that desire/arousal anymore.

Ultimately, I feel deflated at starting so late, like an inept idiot. I don’t feel like a real man. I’m now 29, and going to be 30 this coming March. I feel like I’ve wasted my youth and my 20s, which is difficult to come to terms with. If I was not deemed attractive in my so-called prime, how will things ever get better? In real life, I’ve been on many dates, get lots of matches on apps, and even hit on at bars. These occurrences do nothing to improve my mental state or outlook. I still feel like there’s a massive gulf in experience with other men. I do struggle with initiating or expressing interest in someone, because I still think I’m an ugly nerd. I’m just exhausted about feeling so invisible.

I really don’t know what to do. I feel like I’ve missed out on so much. I am on anti-depressants (SSRIs) and have lost my sex drive. To me it’s not about pleasure anymore, just a source of insecurity and inadequacy. I don’t like thinking about sex, because it makes me feel inferior. I feel like I cannot recover from this, and am always bitter, and resentful of others. It seems so much easier for most men. I had the tools to succeed. Had the ability to be a good partner, I know I can please a woman, but I feel like a lost cause.

SSRIs have brought some stability to my life. I have been suicidal, and lost close friends and family members during my 20s (untimely deaths). I just feel like a bundle of grief and regret on certain days.

I’m not sure what I’m asking here… I want to get better and have the attributes to be a decent catch or boyfriend. Things just never added up for me. I don’t know how to shed this negative self-image. This quarantine period (stuck in a small town where I don’t know anyone) has been very, very trying for me. I imagine it’s the same for many others.

Thanks for all you do,

Hopelessly Adrift

DEAR HOPELESSLY ADRIFT: First and foremost HA: there is absolutely nothing wrong with having not had sex or having been a virgin slightly older than the average. I mean, even just counting the number of letters I receive from people just like you and clients I’ve worked with who have been older  than the national average, you are emphatically not unique or even uncommon. Lots and lots of people didn’t have sex or relationships until their 20s, even 30s and 40s. That’s not “abnormal”, my dude. That’s just that you’re someone who is a little shy and soft-spoken and who was apparently surrounded by assholes.

The biggest problem you have is that you’ve taken bulls--t ideas about “what it means to be a man” and internalized them to the point that you can’t bring yourself to take the wins when you have them. Take, for example, your first partner. Not only was she caring and supportive, but you were able to please her, sexually. But the toxic idea of what a “man” is has convinced you that since you didn’t do it just with your penis, it doesn’t “count” somehow and you believe that she’s going to mock you for having only pleased her with your hands and mouth. Which is, again, for the cheap seats, bulls--t.

(Also, just to be clear: that’s how the majority of women reach orgasm during partnered sex. Most women don’t achieve orgasm through penetration alone; they need clitoral stimulation that’s most easily and efficiently achieved through oral sex or manual masturbation.)

You had sex, my dude. If you weren’t 100% hard during penetration or you lost your erection? You still had sex. Even if you didn’t have penetration at all, you still had sex. Virginity is a f--king construct my dude; it’s not a quantum state that’s only changed by getting a diamond hard P into someone else’s V. Otherwise there’d be a whole lot of folks who have a metric f--kton of sex who’d be virgins for life.

Just as importantly: you haven’t wasted s--t. Hey, you didn’t party like movies tell you you’re supposed to in your 20s… big fat hairy deal. That doesn’t mean your 20s were wasted, it just means you didn’t party or f--k around. That’s all. You were doing a bunch of other things that are just as valid, just as real and just as legitimate. Did you learn about yourself? Did you grow and improve? Did you try new things, have new experiences? Congratulations, you didn’t waste your 20s.

And like the sage once said:

You young boys gotta chill

30’s the new 20, —— 

I’m so hot still

Let me reassure you: the only people who give a six-legged rat’s ass about how much “experience” you had are a) asshole dudes and b) you. Women, on the whole, don’t give a damn about your sexual resume. The women who are going to date you and sleep with you aren’t dating your number, they’re dating the whole you. The only reason why this would be a problem would be if you pre-reject yourself or — worse — insist that a woman doesn’t like you even as she’s insisting that she clearly does.

Plus: as someone who did a lot of unlearning and re-learning in my late 20s and early 30s, I can tell you from personal experience: my 30s were way better than my 20s would’ve been, if only because I had more life experience and better credit.

And by the way: a big reason why you’ve lost your sex-drive is because you’re on SSRIs. Trust me, been there, done that. It’s a known side-effect of a lot of anti-anxiety meds and antidepressants.

Now what should you do? Well, this is a time when you talk to a therapist and work on these issues. Clearly you’ve talked to someone to get on the meds… if they’re not helping you, then it’s time to find a different therapist. I highly recommend checking the American Association of Sexual Educators, Counselors and Therapists’ referral directory to find a sex-positive therapist near you who’ll help you work through those issues. And, incidentally, there are other antidepressants and anti-anxiety meds that will help you without killing your libido dead.

Just as importantly: work on getting to know some of the folks around you. Yeah, the pandemic makes it difficult, but I’m willing to bet that there’re MeetUps and other organized events that’ve moved to Zoom and other apps. Now’s a good time to start making connections in your area; not for dating, but simply so that you have more friends; having a social circle and support network is important, both for your mental and emotional health but also just for your overall well being. Meet some awesome people, make some cool friends and you’ll realize just how much you’ve been beating yourself up for no good goddamn reason. And the better you start to feel about yourself, the easier it will be for you to start meeting some awesome women who are dying to meet a guy just like you.

You’re in a tough place man, I get it. But trust me: those feels aren’t reals. It’s just toxic masculinity f--king with you. You’ve got far more to offer and far more going on than you realize. The more you’re able to dig out the bulls--t you’ve internalized, the happier you will be. And it will all go much faster than you realize.

You’re ok. I promise.

All will be well.

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 thought about writing in before but I’ve never had enough real motivation until now. I’ll try to keep it brief. 

Over the last 7 years (woof, that long already) I’ve developed a FWB situation with a woman I met in undergrad. We texted on and off for most of the first half of the decade until we lived closer to each other. Then we began hooking up in 2017-2018 until she called it off in fall of last year.

We’ve become pretty good friends over the course of us knowing each other, and I care deeply about her. However, she’s not really as invested, which is why she called it off , which is fine. That’s normal. Stuff like that ends. It’s just begun to feel unhealthy in the last year.

After she called it off, we agreed to give each other some space, but we keep coming back to text each other. Neither of us want to admit it, but she likes the attention I give her, and I like being in close contact with SOMEONE who cared enough to f--k me. I’ve tried to tell her that it’s often painful for me to continue talking to her because I’m not over her, but she won’t stop. And I give in every time because I’m craving SOME kind of intimacy (even if it’s just a ghost of it).

Is there a way I can break this off? I feel kind of used for attention. She’ll even sometimes send me music that she knows will turn me on. Like. In a flirty way. But sometimes she’ll shut me down if I try something similar. I can’t let her go and it’s starting to feel kind of co-dependent. What should I do?

One Sided Affair

DEAR ONE SIDED AFFAIR: This one’s easy, OSA: boundaries, boundaries, boundaries. You need much stronger boundaries with your former FWB.

You’re 100% correct: she’s digging on the attention you give her. She may not be emotionally invested enough to keep up the benefits part of the relationship, but she’s clearly not willing to give up the charge of knowing that you still want her. That’s why she’s playing this game of “go away a little closer”; she’s giving you just enough of her attention to keep you hooked, but without ever actually paying off what she’s offering. That’s why she’s willing to flirt and flirt and tease and tease, right up until you start to make noises about taking this somewhere more interesting with accompanying squishy noises. She doesn’t want the affair, she just wants the knowledge that you want her, even though she doesn’t want you.

Quite frankly, it’s a power-trip for her. As long as you’re letting her get you wound up, she has power over you, power that she expresses by teasing you and then shutting you down. And, y’know, if you were into this sort of weird ass orgasm-denial play or you had consented to it when you ended your FWB relationship, that’d be one thing. But you aren’t, you didn’t, and this is actively hurting you and making it harder for you to get over her.

Similarly, it’d be one thing if she didn’t realize how much this was hurting you. But she does. You straight up told her. And she’s continuing to do it anyway.

That tells me pretty much everything I need to know about her. And it tells me what you need to do.

But you aren’t going to like it, my dude.

As much as I hate to say it, she didn’t just end the “with benefits” part of your relationship; she also ended the friendship. The way that she’s treating you is not how you treat a friend. She’s actively disrespecting your request that she stop teasing you and flirting with you because to do so would be inconvenient for her. It would deny her whatever thrill she’s getting from your continuing to be in her life and continuing to want her. It’s cruel and it’s unfair to you and if she actually cared about you, she’d goddamn listen when you said “stop“. But she didn’t.

Just because y’all had a casual relationship doesn’t give her the right to treat you casually.

The only way to break this off is to make a complete and clean break. First: tell her, straight up, that you’re ending things and why. You can’t have her in your life when she ignores your very reasonable requests to stop flirting with you. You especially can’t have her in your life when her behavior hurts you and makes it harder for you to get over her and your relationship together. Send her an email, a text, something, and them immediately take the Nuclear Option. That means blocking her on social media, blocking her number on your phone, deleting her Skype handle, taking her off your Venmo… every way she has of getting in contact with you or worming your way back into your life. And it needs to be immediately after you send that last email. You will feel as though you owe her the chance to explain or to make things right. You don’t, and she won’t. This will just give her the opportunity to do what she’s done over and over again: reel you back in. You already know that you have a hard time saying no to her, so don’t put yourself in the position of having to. She f--ked around, and now it’s time for her to find out.

The thing to keep in mind: this isn’t about punishing her. This is about enforcing your boundaries. Boundaries are useless if you don’t actually enforce them. If you draw a line in the sand and don’t do anything when someone steps over it, all you’ve done is tell them that your requests are optional. Having strong boundaries means that there are consequences to actions, yours and theirs. In this case, the consequences of her actions mean that you cut her off. The consequences of you enforcing your boundaries means losing a friendship you’d rather not have to give up. But, unfortunately, she’s proven that she’s not worthy of being friends with you. She has given up that right through her actions, and it’s time for you to do what you need to do in order to protect yourself.

As a wise man once said: “I may love you, yeah, but I love me more.”

It’s time to love yourself enough to tell her to go away and make it stick.

It will suck now, but you’ll be better for it — both in the short term, as you get over her, and in the long term as you learn not to let someone treat you this way.

It’s a sucky situation, and I’m sorry that it’s come to this, OSA. But this is the best thing you can do for yourself.

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 have been an avid reader of your blog for a few years and have finally mustered the courage to ask for advice. I really enjoy the laidback approach to answering some really serious matters, and the fact that you provide pictures of cute animals when things get really serious or disgusting. And of course the nerd culture references, especially anime references.

I understand that while I am from India and given the different social and cultural customs it might not be the wisest idea to ask someone living in the US for non academic advice, right now I would appreciate your advice. I honestly haven’t found any Indian contemporary who is not misogynist or believes women are a hive mind.

As for my background, I am a 25 year old dentist planning to pursue a master’s degree. I live with my parents and elder sister, which is pretty normal in India.

My parents are a classic example of everything that can go wrong in a relationship. My father is financially opaque and allegedly is more involved in his brother’s family and way more interested in chatting with strange women on facebook and watching really crude porn (he always downplays it by saying that he pressed some weird link, but that is all a lie, he is tech savvy enough to know how to block his facebook account) and complaining about my mother to anyone and everyone he meets, including me. My mother sees that as tantamount to cheating. Even prior to that she has felt that he is diverting more of his earnings to his brother’s family (who is employed).

This is not to say my mother is without blame. She has been narrating tales of all the injustices to me and my sister for as long as I remember, emphasizing how she sacrificed her pleasures after becoming a homemaker, while my father would be the representative of the family at all the gatherings of our extended families. I sometimes have felt sorry for my father who is never appreciated for whatever little he still does. Mother being a chronic complainer always sees the glass as half empty. 

Even my father has recently resorted to using emotional blackmail against me and my sister. For example, he likes to repeatedly mention how he gets emotionally hurt every time I have to physically shove him away from my mother when things turn nasty. When I reason that violence is not negotiable he counters by saying that I should atop mother’s nagging. It is like if mother uses words, he’ll use his fists. He wants to get a licence to hit my mother without consequences. And things get nasty, slapping, hitting with sticks and there was one time when he bit my mother on the arm.

For my parents, the house and the cyberspace are war zones and they must gather people to their sides. Their arguments stem from ridiculously petty issues but escalate to trash talking and in bringing up events that happened before I was born.

It comes as a surprise to me how I remained a good student all through my school years and eventually have become a dentist. 

The only impact of my parents’ toxicity that I am aware of is that I have grown to be extremely wary of expressing anger in particular and confrontations in general. My social life has been rather ordinary, even today I have a few friends from my school days with whom I am in touch. In dental school too I have been friendly with my peers, only the coming years shall tell me how many of them will remain in my life but I am optimistic.

What I wish to know from you is how should I approach dating. 

Seeing the disaster my parents are, I have no intention of getting matched with a person I have no compatibility with or to even have her live with them. I fear she’ll become just as bitter, resentful and toxic as they are. The conclusion I have made at present is to focus on my education and career, get a place of my own away from my parents and then think of dating. 

But I cannot exactly control when people come in my life. In India, most women get married before thirty and I fear that by the time I have enough money for a house away from my toxic parents (I assume i will be in my mid thirties by the time I become financially independent) there would be no single women left. Even during my years in dental school, three women got married and one of them gave her graduation exams while pregnant! It kind of like a biological clock for men.

This is what is always on my mind whenever I am interested in someone at the present moment. Though I fully understand that not all relationships will end in marriage and may collapse after that too, I don’t want to be the kind of person who is dating without any end point in mind. This may be an atypical thought coming from a man born in the late nineties by that is my old-fashioned way.

And I don’t think that anyone is there to “go on a journey to build and grow together.” Everyone seems to want the finished product, not a work in progress, financially or emotionally.

And to top it all off, it might all be pointless since the woman in question might be married off by her parents to someone else anyway. (Arranged marriages are very prevalent in India). Of course that applies to me too, but I don’t want to go down that path knowing how badly it can get when living with someone you are not compatible with.

I will appreciate your regarding my situation.

Thanks in advance. 

Joyless in The City of Joy

DEAR JOYLESS IN THE CITY OF JOY: So I’m going to have to give an obvious caveat at the start of this, JTCJ. Like you said: I’m an American and you’re living in India. There’s going to be a difference in outlook, culture and customs, and I’m going to be ignorant of circumstances on the ground that folks in Calcutta would find obvious. So I’m going to apologize for any blind spots in advance and recommend that you take my advice with suitable amounts of salt.

And with that, my thoughts.

My first thought is that arranged marriages aren’t automatically joyless or, worse, full of animosity. I actually have friends from India and Pakistan who chose arranged matches, and their relationships have been successful and happy. One of the keys for their success had been a willingness to take things at a relatively sedate pace; after they met people that they found interesting and compatible, they spent some time getting to know each other before getting married, with the acknowledgement that they could call it off if they had reservations. Another was that they (and their matches) focused on compatibility and mutual respect in who they were looking for. But most importantly were that they acknowledged that they were going to have to work to make their marriage successful. That meant that they were going to have to prioritize clear and open communication, to make sure that they understood each other. They also had to be mindful of how they handled disagreements and fights and make sure that they were actually resolving issues instead of just trying to stop the fight. That way, they weren’t going to be hoarding resentments and grievances like a passive-aggressive squirrel, storing hate-nuts for the winter. And they made a point of complimenting each other, admiring each other and expressing gratitude and their appreciation for one another; in fact, they made a point of trying to keep a fairly solid ratio of compliments to complaints. Complaints can trigger our inherent negativity bias, which makes them hit five times harder than compliments and gratitude. That makes it important to try to ensure that you don’t only appreciate or admire your partner, but that you express that appreciation, openly and frequently.

My second thought is that, well, they f--k you up, your mom and dad. It sounds like your parents marriage was a nightmare to grow up with, and I’m sorry you and your sister had to go through this. But while you can’t change your past — or your parents — their marriage doesn’t have to be your destiny. In fact, you’ve made the conscious decision to try to avoid that, which is awesome. Having that template of “ok, here’s what I don’t want” gives you something to build from. Because you’ve seen the way that bitterness and resentment can fester, you can look at the behaviors, beliefs and attitudes that lead to your parents acrimony and make a conscious choice to do things differently. They’ve given you the map of the traps and pitfalls that their relationship fell into, and you’re in a better position to avoid them.

Of course, knowing what you don’t want doesn’t automatically translate into knowing what a positive relationship looks like. And while there are some things that you can only learn through experience, I would suggest is that you might want to look for positive relationship role models. Those may be the marriages of friends or the parents of friends who are happy and nurturing. Talking to them about their experiences may well go a long way to helping you map out what you’re looking for and how to achieve it in your future relationships. Or, failing that, you may look to examples in pop culture for the kind of relationship you would want to have and work towards developing the skills and communication that you would need to help encourage that sort of connection. They’re not a perfect guide — after all, those relationships work because the writers say they do — but they can go a long way towards helping shape what you would want your relationship to look like.

(And here, I have to confess: I have a fairly limited knowledge of Indian pop culture, so I don’t know who I could recommend; perhaps readers could provide some suggestions. Though I will always recommend Gomez and Morticia Adams as an excellent starting point…)

My third thought is to be careful about falling into traps of making assumptions about others, especially on the individual level. While there’s a strong tradition of women marrying young, that doesn’t mean that every woman is looking for someone who’s a “finished  product”, nor is that even necessarily what they’re looking for. One of the ways that men can make dating harder on themselves is that they often end up responding to what they think women expect or are looking for, rather than what women actually want in partners and relationships. This is one of those times when having women as platonic friends is incredibly helpful; it gives you a much more accurate idea of what women want, as well as what their dating and relationship experiences are like.

By that same token, while I understand that you’re worried that there will be a shortage of single women by the time you’re ready to date… well, I hate using this phrase but feels aren’t reals, man. This is an incredibly common — and cross-cultural — anxiety in men; they worry that if they don’t pair up by some artificial deadline (usually their late 20s) then they’ll have run out of available women to date. Why? Because they’ll all have settled down and found boyfriends and husbands.

Except that’s not true. Even in conservative cultures, or cultures where there are traditions of marrying young, there are still people who don’t follow tradition or who don’t want to get married that young. I suspect that your experiences and outlook on relationships aren’t as uncommon as you might think, for both men and women. In fact, I suspect there’re more people than you realize who feel the same way, and it may well be worth your time to seek them out. These could be networking events for young (and single) professionals, social organizations, even just clubs for people who dig movies, anime or what-have-you. Expanding your social circle will go a long way towards helping you meet more like-minded folks… including women who may well be looking for someone to grow with, rather than someone who’s “finished”.

But more than anything else: pursue relationships with intention, modeling the kind of relationship you want and the behavior you want to see from your partners. And don’t be afraid for you and your partner to write your own “rules” for your relationship. One of the reasons why relationships will often fall apart is because they try to force themselves into a relationship model that doesn’t fit them. But the great thing about life is that you don’t have to follow other people’s rules; your relationship is a collaboration between you and your partner. While other people may have opinions, they don’t get a vote. You and your partner can define for yourselves how you want this relationship to work, what rules the two of you agree to follow and how you want things to progress. When you find someone you’re compatible with, the two of you can decide what you want your relationship to be.

Now in fairness: sticking to your guns and making sure that you find the partner (and relationship) that you want may mean being single for longer than you’d prefer. It could take time to find somebody who’s right for you and who you’re right for. It’s understandable that you may want to examine your “must-haves” and decide that maybe you can be flexible on some of them. That’s a completely valid decision. However what you don’t want to do is drop your standards out of a fear of being single. Getting into a Somebody, Anybody, Everybody relationship — where you’re just trying to fill the hole marked “girlfriend” or “wife” — is a great way to end up in a bad relationship. It’s one thing to compromise; it’s another when your relationship is compromised from the start. Make sure that you’re getting into a relationship with someone because you want to be in a relationship with them… not because you want to be in a relationship.

You’ve got a lot going for you, JCTJ. You know what you want, you’ve made great choices and you’ve got a game plan for a solid life. That’s all to the good. Don’t let your worries overpower your goals; the fact that you’re worried about something doesn’t mean that there’s actually something to worry about.

Good luck.

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