DEAR DR. NERDLOVE:, first off I’m a big fan of your site and really appreciate all the healthy dating advice you give. I’m a 26 year old straight male and I’ve basically had intense shame about my sexuality for my entire adult life. It’s really held me back and makes it extremely difficult/impossible for me to seek out relationships.

Some background, and apologies if this is a bit long. I got my first girlfriend back in college when I was 17. We dated for about 10 months and I didn’t realize it at the time but it was an INCREDIBLY unhealthy relationship. I’m now fairly sure she had something like borderline personality disorder, but being naive I mostly just took it upon myself to change to make her happy. She was extremely jealous and passive-aggressive, would accuse me of cheating if I so much as talked to another girl, would constantly explode at me over the tiniest things, made me basically cut most of my friends out of my life, etc. She also very early on (within a few months) started to frequently pressure me to agree to marry her, which I was extremely uncomfortable with but eventually gave in to and said I would consider it. But the worst of the problems revolved around sex.

Initially she seemed very interested in sex (she was not a virgin) and would talk about some kinkier stuff she wanted to eventually try. To my surprise, she said that she didn’t want to have sex until 6 months into the relationship, which I fully respected. However, she would somewhat frequently perform oral sex on me (never on my request, it was always her initiating) but would always turn down my offers to reciprocate. After 6 months we did start having sex, though it was very infrequent (I think maybe 4 times total). She always acted into it before/during, but afterward she would immediately call her mom and talk in front of me in Chinese (no idea what she was saying but it was very uncomfortable), and would seem upset/passive-aggressive for a while.

She had some really nasty sex-negative views which we would frequently disagree about. For instance she believed that a woman should only have sex with a man who was willing to marry her, otherwise she would be “devalued”, and that sex was a thing that women did for men to keep them happy. She would also slut-shame girls who dressed in revealing clothes.

Eventually, near the end of our relationship, she revealed that she apparently hated sex, thought kissing me was disgusting, and didn’t even like hugging me. Rather than being flattered/happy that I found her attractive, she basically took it as an insult. I said that we didn’t have to have sex or kiss anymore if she didn’t like it, so we stopped.

I should also note that during this time, my dad dumped my mom after 20 years of marriage for a woman 20 years his junior. It had devastating effects on my family, particularly my mom, and I hated my dad more than anyone in the world. I promised to myself that I would never be anything like him.

Finally after maybe a month or so of no sex, my girlfriend and I broke up, and she said some of the most hurtful things I’ve ever heard in my entire life: that I didn’t love her and that I only used her for sex, and that I was “just like my dad”.

Honestly, hearing this was my worst nightmare come true. Here’s why:

If a woman says no, I will absolutely 100% stop whatever it is I’m doing, and won’t push it.

If a woman seems hesitant but doesn’t say no, I will absolutely 100% stop whatever it is I’m doing and ask her if she wants to continue.

If a woman says yes/seems enthusiastic then I can trust that as a great sign to continue, right? … except I can’t.

Apparently for all those months, my ex-girlfriend hated sex and felt used/forced into doing it but said nothing. This is so incredibly horrifying to me. I was basically… forced to rape someone for months without realizing it.

On top of this, what my dad did, and the accusation that I was “just like him”, have caused me an incredible amount of shame over the mere fact that I’m sexually attracted to women in general.

After breaking up with my ex-girlfriend, I didn’t date or have sex or any relationships for over 5 years. I went into a pretty terrible depression and eventually got therapy for over a year.

I finally managed to find a girlfriend via online dating and we dated for a bit over a year and it was a MUCH healthier relationship.

However, it’s been about 9 months since we broke up and this deep-rooted shame is still really holding me back. I occasionally work up the courage to introduce myself to women and I’ve managed to go on a few dates via Tinder, but I’m absolutely incapable of making any sort of romantic/sexual moves, so the dates all just go nowhere.

In my mind, making a move = creepy, sexual assault, unwanted sexual objectification, irremediably insulting. I know it’s not rational or true, but it’s what I’ve been conditioned to believe. (It probably doesn’t really help that in an attempt to learn how approach dating/sex in ways which are respectful toward women, I spent years reading radical-feminist-esque dating “advice” articles which were basically just big lists of all the ways men should stop being horrible, but no actual advice on what is desired/considered okay.)

Honestly at this point I don’t know how to move past this. I know that it’s unhealthy to focus on the worst possible outcome, and besides, as everyone seems to say, what’s the worst that could happen? You try to make a move but get rejected and it’s a bit awkward, right? Nope, the worst is FAR worse, and I know because it was my experience. I take rejection incredibly well. In fact, I almost prefer being rejected because at least I know that “no means no”, which is way better than “yes but secretly I feel violated/used/raped and I won’t tell you until after/possibly ever”. To make a move on someone means risking that they may feel violated, even briefly, and after my experience with my ex-girlfriend, taking this risk just seems completely incompatible with my drive to be a good person.

At the same time, the fact that I feel this way makes me feel like a nasty sexist asshole because it implies that women are fragile flowers who are incapable of handling a moment of discomfort. Obviously I don’t believe this on a rational level, but it’s the logical conclusion of my deep-rooted fear, and this also makes me feel like a bad person, because I do not want to be sexist.

In the words of Andy from The 40-Year-Old Virgin: “You know what? I respect women! I love women! I respect them so much I completely stay away from them!”

As I mentioned before, I did therapy for a while and it helped me sort out the reasons why I have all these hang-ups, but ultimately I can’t seem to move past the fact that my worst fears were actually proven true, and could happen again.

Do you have any words of advice to offer?

Sincerely, 

- A Guy With Issues

DEAR A GUY WITH ISSUES: Before I get too deep into this GWI… I’m so sorry all of this happened to you. You were in an emotionally abusive, toxic relationship. The behaviors you list at the start of your letter – the explosive jealousy, the way she isolated you from your friends, the emotional mood-swings that always left you afraid to set a toe wrong – are all classic signs of an abusive relationship. The fact that she didn’t hit you or physically abuse you doesn’t change the fact that you were abused.

The things your girlfriend did to you are not your fault. Your ex – and thank all the stars that she’s your ex – was hitting you where you were the most vulnerable. She was going out of her way to make you feel as though you were the bad guy in a relationship. Maybe she legitimately believed it. Maybe she was being deliberately manipulative. Doesn’t matter. She was abusing you and this was not your fault.

Maybe she changed her mind about sex. Maybe she had a bad association with sex. Maybe she was sexually active at first because she had to be but later realized she was asexual. Maybe she was dealing with religious or cultural shaming around sex. Still doesn’t matter.

She was abusing you and this was not your fault. 

You weren’t “forced to rape someone”, GWI. You were dating someone who was at best, dealing with a head full of bad wiring and emotional issues. At worst, you were dating someone who decided to leverage your anxieties against you as a means of control and punishment. You were abused and this was not your fault.

Your father leaving your mother was a tragedy and – again – I’m sorry it happened to you. But what your father did is nothing like what happened with you and your girlfriend. Your feelings around your father were another hammer that your ex used to hit you with. She leveraged the things that you feared and hated most and turned them around on you because this is what abusers do. They gaslight you, they convince you that you’re the bad guy, that you deserve the abuse because of all of your sins and crimes against them. They isolate you from your friends and loved ones so that you don’t have anyone else to turn to, who might have more influence over you than they do. They keep you off balance so that you can never feel comfortable or secure; you have to remain hyperaware of their moods lest they explode at you again. They make sure that they are the only thing you pay attention to or else.

You were abused and this was not your fault. 

You need to accept that damn near everything your ex told you was a f---ing lie. You can’t trust anything she told you to be real because it was all part of the patterns of abuse. It was a way of controlling you and punishing you and keeping you compliant and servile.

I’m not the least bit surprised that you’re carrying around scars and anxieties from this, GWI. You were hurt, badly, by someone who you trusted and cared for. She deliberately inflicted pain on you in the most damaging way that she could. The shame you’re feeling isn’t real and it isn’t deserved, it’s the after-effects of what has been done to you.

But knowing this doesn’t make it easy to shake off. Those scars run deep, and the scars you can’t see – the ones that are inflicted on your mind and soul – are the hardest to overcome. This isn’t the sort of thing you can just will yourself past, nor is it something that can just fade with time. To really start healing from what was done to you is going to take professional assistance, preferably someone who has been trained to deal with these specific issues. It’s good that you went to therapy, but if you didn’t tell your therapist that you were coming from an abusive relationship – especially if you didn’t or haven’t realized it yet – then you weren’t going to get all the help you needed.

You need more than a loudmouth with a blog, GWI. You need someone who’s trained to help victims of emotional abuse and sexual trauma. Fortunately, you can find them. I suggest that you go to the American Association of Sexuality Educators, Counselors and Therapists website; they have a directory of therapists who specialize in issues surrounding sexuality and sexual shame. Find one in your area who deals with victims of abuse. And don’t forget: you can fire your therapist. A relationship with a therapist is like any relationship; if you two don’t click or get along, then it’s not going to help. If the one you’re working with isn’t helping you or you’re not comfortable with them, then find another one.

Don’t let the fact that you’ve been traumatized by this fool you, GWI. The scars you are carrying don’t mean that you’re weak. Quite the opposite: you’re strong. Stronger that you realize. They’re a sign that you survived. You got out of that relationship and you realize that you need help. That’s an incredible strength. You can heal, you can feel better.

Give yourself permission to take time out from dating. Forgive yourself for what your ex did to you. Forgive yourself for buying into her lies. Recognize that you were abused and this was not your fault.  Find yourself a therapist and focus on your healing for now.

You will be better. And write back to let us know how you’re doing.

All will be well.

DEAR DR. NERDLOVE: I want to help my best friend of 10 years. Let’s call him S. He’s gay, came out of the closet back when we were in high school (2009/2010), and has a very supportive family. However, S has always had some self-esteem issues and many of his partners have cheated on him. He often uses dating apps to find his partners.

Just over a year ago he started seeing this guy, we’ll call him D. For the record, I haven’t met D, but I’m my S’ confidante and have seen text messages etc. There are a number of reasons I haven’t met D, the primary one being that he is currently cheating on his live-in girlfriend and no one in his life knows about his relationship with S. If that wasn’t bad enough, he also has 3 kids from two other different women. He doesn’t have custody of any of them (yet), but 1 who has some learning disabilities is moving in with him this summer.

There are a number of excuses that D uses for why he can’t be with S but why he continues to see S anyways. They include: the fact that his girlfriend co-owns the house with him, the fact that he doesn’t want to upset his kids because they are close with the girlfriend, and his business related ventures that always make it an inopportune time to break up with the girlfriend. S stays because he is madly in love with D and because D claims that he’s from an older time and can’t possibly come out of the closet (even though he’s had sexual relations with men before S).

I have called bullshit on D, and explained that at the very least he could leave his girlfriend without coming out of the closet but S always makes excuses for his behavior. I get that kids are involved and should come first, so that part of D’s behavior I can forgive, but it still comes down to the fact that S is clearly the lowest on D’s priority list. I’m also worried about S because whenever they fight D preys on S’ insecurities and often will gaslight S telling him that he’s being too demanding or crazy when S questions D’s feelings for him.

How do I get S to see that he’s just wasting his time and is going to eventually have his heart broken again?

Sincerely, 

Already Tried Intervening

DEAR ALREADY TRIED INTERVENING: So you know that Percy Sledge song “When A Man Loves a Woman”? It kind of applies here: a person in love is often willing to overlook all kinds of BS because love isn’t just blind, it sticks its fingers in its ears and goes “LALALALALALALALALALALALA I CAN’T HEAR YOU”. And that is intensely irritating for everyone around the fool in love because sometimes you’re yelling at them that they’re about to do a Wile E. Coyote off a cliff.

Unfortunately, you can’t force someone out of willful blindness. Because that’s what’s going on here: your boy S is being willfully blind. Maybe it’s sex-fueled thinking, maybe it’s issues about deservedness that lead him to chasing after someone he knows he can’t have. Whatever the root cause may be, S has chosen to pursue this guy and you can’t make him change his mind. S is going to keep walking off that cliff until the day he looks down and gravity kicks in again. Which will happen.

It’s glaringly obvious that D is not going to leave his girlfriend or come out of the closet. This puts S’s relationship with him on a timer that’s going to run out, sooner rather than later. It’s only a question of when it ends – likely messily and all over the place.

You can’t argue S out of wanting to be with him, nor can you stick toothpicks under S’ eyelids to force him to see. He will always point to D’s reasons. But D’s reasonings – whatever they may be – don’t really matter. They’re just excuses. What matters is that D is hurting the people in his life – S, his girlfriends and also his kids. And someone who’s willing to do that to people who love and care for him is someone who has stamped themselves with DO NOT DATE.

The only person who can make S realize that… is S. Pushing harder against this will ultimately run the risk of pushing S away because let’s be real: nothing makes love more appealing than when the world is telling you that you can’t have it. Sex almost always wins in the end. And the last thing you want to do is push S away because when this blows up – and it will – he’s going to need you, more than ever. So have one last conversation with S on the topic. Point to the ways that D is signaling that he will never leave and that the relationship will never be what S wants. And then… drop it. Let him know that this is the last time you’ll discuss it with him, but you love him and support him and you’ll be there when – not if, when – he needs to talk with you over this.

And when it does blow up… don’t tell him “I told you so,” ATI. He’s already going to feel used and humiliated; don’t rub it in. Just be the friend he needs – even if he didn’t listen to you when he should have.

Good luck.

Dr. Nerdlove is not a real doctor. 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 in my late 20s, “pushing 30” as they say. I’ve never been in a relationship or had sex. I’ve suffered from anxiety, low self-esteem and depression much of my life, though I am taking medication and going to therapy. My dating life can best be described as a series of disappointments. All my attempts to ask women out in person (admittedly few in number) have ended in rejection, and my online dating history has hit a wall in the past year. I was having some success with online dating, but nothing that went beyond three dates. I haven’t been on a date in about a year now, partly due to the fact that I’ve been coping with the death of a close loved one, which basically shut me down entirely for a few months.

I think I have a high sex drive. I masturbate almost daily, sometimes multiple times a day. But Doc, all I’ve got is porn and Instagram models, you know? I’ve never so much as touched a titty or had an intense make-out session. I’m so far behind when it comes to sex and dating. So many people I know are getting married, and I still haven’t even had a single relationship yet.

I had always hoped I could lose my virginity to someone more experienced than I am who would help guide me through it, you know? But it feels like the older I get (again, pushing 30 here), it’s less endearing being a man with such little experience, and more like a glaring red flag.

I would like to gain more sexual experience. I’d like to play the field and have lots of casual sex. But first of all, I’m not hot enough to pursue casual sex (I’ve struggled with my weight my whole life, a huge factor in my poor self-image and lack of self-esteem and confidence with regard to dating, and I’m technically obese according to BMI). I know there are women out there who like bigger men, but that seems like kind of a niche subset of woman. It seems most women want either a guy with abs or a skinny Timothy Chalamet type they can baby. I’m SOL in that regard. I’m hitting the gym, but it’s going to take months, if not longer to begin to be in the kind of shape I want/need to be in to search for hookups. Second, I’m of South Asian descent. I don’t want to harp on this too much, but I know we’re not exactly the most popular ethnic group in the west, and I’ve read the statistics on response rates in online dating. Generally, I’m under the impression that most women simply aren’t interested due to my ethnicity. Add in my weight, and I’m already at two strikes while at the bat.

I can’t stand the dating apps anymore, so I want to avoid that avenue. But I just can’t see myself going to bars or clubs trying to convince someone to hook up. But I NEED sex, Doc. I’m going insane just jacking off. I’ve been seriously considering hiring an escort or flying out to Reno just to get the deed done. Maybe it’ll help “clear my head” and put me in a better state of mind to pursue sexual intimacy once I’ve actually done it. Just some intense petting and making out would probably do it for me at this point, doesn’t even have to be full-on-sex. What should I do, Doc? Should I pay for it to get it out of the way, or are there other venues I should try that aren’t online dating or bars? I feel like I’m running out of time, and that’s what scares me most of all. With every day that passes, I get closer and closer to being a 40 year-old virgin, and right now that seems the most likely outcome.

Unicorn Bait

DEAR UNICORN BAIT: Alright, I’m going to do something that I don’t do very often, UB: I’m going to give a bit of behind-the-scenes access here. This isn’t personal, so much as you just happened to be the lucky thousandth or so letter on the topic.

I picked your letter specifically because at this point I’m getting more than a little tired of getting questions about virginity that are so cookie-cutter and following the same tropes and complaints that it’s hard not to notice they follow a formula and they’re more or less all stemming from the same place. So rather than talk about what you should do, I’m going to talk about what these questions are actually about.

Spoiler alert: it’s not about sex. It’s about being validated.

9 times out of 10, literally, they bring up the same worries, the same complaints and more often than not, weird “nobody will ever touch a virgin because if someone else didn’t that means that there’s something wrong with them”.

Bonus points if they try to justify it by complaining about how it makes women think they’re a terrorist because of incels like Minassian, Rogers, etc.

This is frequently paired with complaints about how women only want certain body types or guys who look a certain way, frustrations with online dating and of course, the difficulties of navigating the bar and club scene.

The thing is, virginity is a money-soluble problem for men; sex workers exist, after all, and is legal in many places. As you say in your letter, UB: a trip to Nevada is relatively cheap (airlines have regular sales) and most of the legal brothels will even send a car to pick you up at the airport. It neatly solves all the problems someone might encounter if what they’re looking for is to lose their v-card status – you take away any question of whether or not sex will happen, you know exactly who you are going to sleep with, that they’ll be attractive to you,  and more often than not, it’ll be a positive experience because your partner will be focused entirely on your pleasure. As a bonus, most escorts are going to understand the issues most likely to come up (loss of erection, premature ejaculation, good old-fashioned stage fright…) because they’ve seen it before and handle it with grace and compassion. Many even offer what’s known as a Girlfriend Experience (that is: a session that feels more like time with a partner rather than a commercial transaction) or focused around first-timers.

But this is almost never the route the virginity-afflicted choose… not because of money or inconvenience – you’re likely paying more over time for roses on Hinge or Tinder Gold subscriptions and getting less for it – but because of what it means. Specifically: that they didn’t lose their virginity in “an authentic way”. Amusingly, this isn’t that far from the discourse around weight-loss drugs like Ozempic, when people tut tut over not losing weight “properly”; if the concern is truly about whether or not someone’s a virgin, why would it make a difference if their first time were with an escort rather than, say, a semi-drunken fumble with someone who was looking for the least objectionable warm body after closing time at the bar?

This is, to my mind, the single greatest example of how virginity is a social construct. If meeting the commonly held definitions of penetrative sex – tab a into slot b, repeat – can be disqualified because someone paid for it, then the issue isn’t virginity.  

The real issue is the desire to be chosen. To have their inherent desirability validated by the fact that someone chose to have sex with them, instead of with someone else. It hinges, in no small part, on the idea that women are the “gatekeepers” of sex and thus the ones who bestow validity on someone by f--king them.

It’s not really a surprise, then, how often these letters follow the same tropes and complaints. After all, they’re frequently coming from the same place – literally and metaphorically. They’re coming from people who have absorbed toxic ideas about what it means to be a man, mistaken ideas about women that, likewise, come from other men rather than from women and then buttressed by giving credence the worst or most reactionary takes that social media algorithms can throw at them without ever stopping to consider that maybe the subreddits or Discord servers they’re frequenting aren’t a reasonable or even representative slice of humanity. Especially when it doesn’t take much to go outside, look around and see how many imperfectly-shaped people are having sex, having relationships and otherwise living their lives despite not looking like INSERT_MALE_CELEBRITY_HERE.

This gets all the funnier as folks decry that women only want whichever celebrity they’ve zeroed in on, while women are out there talking about the horrible things they’d let Matt Berry or Jesse Plemons (or other folks who don’t look like they were carved out of marble and abs) do to them.

You’re not going insane from a lack of sex, UB. You may be horny, sure… but the issue isn’t going to be solved by a sloppy make out or a blowjob in a dive bar toilet. It’s not going to “clear your head” and make you feel less anxious, because the issue isn’t “haven’t had an assisted orgasm”. The issue is how you feel about yourself and the fact that you’re looking for someone else to validate you and tell you that you’re worthy.

But as I’m always saying: women aren’t Mjolnir. Women don’t just sleep with “the worthy” – and honestly, you just have to look at the relationship problems women write in about. They have sex for a voluminous litany of reasons, just like men do. Nor are women the “gatekeepers” of anything. While women are often the passive partner when it comes to initiating approaches with an eye towards relationships or hook-ups (for sociological and safety reasons, not lack of desire or a wish to see men dance to their tune), who approaches and who is approached doesn’t decide who the “gatekeeper” is. The approach is just the start of the conversation. The decision about whether they want to have sex is double-opt-in; the only difference is that men don’t think of the times they’ve opted out as counting because they’re more focused on the ones they’ve chosen.

Any woman, however, who’s had an unrequited crush on a guy or a guy who completely missed (or ignored or rebuffed) their attempts at signaling interest can tell you: guys are just as much the gatekeepers of sex as women are.

Your problem, UB, isn’t that you’re looking for loving in all the wrong places. There aren’t going to be magic venues that will eradicate the problems you’re facing, because the issue isn’t where you’re looking, it’s how you feel about yourself and the presumptions you’ve made about women. Your age isn’t the handicap you think it is, because it’s not the age that makes an “older” virgin less and less appealing, it’s their own attitude and beliefs about themselves.

Considering that you don’t consider yourself to be a catch, it’s going to be a lot harder to find women who will respond positively. Not because you’re right and there’s something unappealing about you, but because if you don’t think you’re good enough to sleep with, why would someone else think that? Nobody buys a brand of chips because they marketed it with “we kinda suck but maybe you’ll like us?”

This gets paired with the fact that your biggest handicap with dating involves the women you’ve made up in your own head to reject you. Your letter is littered with suppositions and guesses – “it seems”, “I feel like”, “I’m under the impression that…”. The only person who’s decided that you’re “two strikes before you’ve even gotten up to bat” is you. You and you alone are the person who’s decided that this has already happened and so now you’re barely willing to give things an honest try to the best of your ability. You’re half-assing your attempt to get ass; it’s hardly surprising that it’s not working out.

It also doesn’t really help that you’re hoping for two, relatively incompatible things. The odds that you’re going to find someone who’ll ‘show you the ropes’ but then won’t be an impediment to your then taking your newfound knowledge and going out to just carve a swath through the bars and clubs are low. You’re much more likely to find someone who’s going to be interested in teaching you what to do in the context of a relationship. Sex, as a general rule, tends to be better with someone you actually know and have a continuing connection to; you’re learning more about what they like and what you like and what works for both of you. A relative stranger isn’t as likely to have the same investment in guiding you through things – especially if it’s going to be a one-and-done. While you do occasionally find someone who’s willing to be an an angel investor in the startup that is your sex life, they’re few, far between and not likely to be doing so with someone who mostly views themselves with a mix of contempt and self-pity.

You have a similar issue when it comes to finding casual encounters. The math that women do to decide who they might or might not want to have a quick fling with is less about objective hotness and more “is the sex going to be worth the potential risks”. Considering the orgasm gap that exists in most hetero pairings and the fact that a lot of guys who are looking for casual sex have a “got mine, screw you” attitude and don’t bother bringing their A-game, a lot of women are going to nope out without some serious signs that this is worth it for them. A guy who walks around with the attitude that he’s been pre-rejected before he’s ever said anything is not going to be conveying that Studly Good Night energy. That’s not about bedroom experience or hotness, it’s entirely about attitude and social skills. A virgin with a willingness to listen without ego and a can-do attitude is going to be more desirable than a dude with numbers that would make Wilt Chamberlin blush but who thinks that foreplay is something that happens to other people.

Now, that doesn’t mean that there can’t be challenges, don’t get me wrong. Asian men have long dealt with racist beliefs and portrayals of them as emasculated or less manly. Fatphobia is very much a thing. But as frustrating as those legitimate challenges can be, by accepting them as reasons why you’ve got two strikes against you is tacitly accepting that the other people are right, rather than seeing the folks who buy into it as wrongheaded (if aggravating) fools who are missing out on the best sex they’ll never have. If you’re going to start from a position of “they don’t like me and I have to work my way up to ‘neutral’” then you’re never going to have the confidence or sense of security necessary to actually get laid – certainly not to have sex that’s in any way fulfilling and enjoyable.

While you don’t have to think that you’re the hottest thing since World War III, you do need to believe in your own value, your own desirability and that being with you would be a good thing. If you don’t believe in yourself first, nobody else is going to be that invested in changing your mind – certainly not people you don’t already know. And as many folks who read this column can tell you: having to reassure someone that yes, you do bang like a screen door in a hurricane over and over again is incredibly tiresome and a libido killer.

So if you’re not going to go throw money at the problem via a guided experience with a sex worker, then your best option isn’t going to be dating apps or bars and clubs. It’s going to be working on yourself. Not getting Marvel Chris fit, but learning to not just love the s--t out of yourself, but to connect with people on a social, intellectual and emotional way. Develop your self-esteem and your social skills. Learn how to make people – not women, people – laugh, feel good and otherwise enjoy themselves in your presence. Focus on connecting with folks and also how to express not just confidence but desire with confidence. Don Draper – human trash fire than he is – is charismatic in part because he doesn’t feel ashamed of expressing interest in people.

Once you stop looking to others to prove that you’re worthy, you’ll find more people who’re going to want to see if they can lift your hammer.

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

DEAR DR. NERDLOVE: Growing up, I had a front row seat to my parents’ divorce. Calling it ugly would be an understatement. Everything, literally everything about the process was the start of a screaming match between them, from custody arrangements to dividing up the record collection. I watched what had been a loving and sweet relationship devolve into two strangers who apparently hated each other more than life itself and it left me terrified that I was going to have a similar fate if I ever got married.

Now it’s many years later, I’m 28, I’m engaged to an incredible woman and we’re just at the start of planning our future wedding. But I would be lying if I didn’t say that the specter of my parents’ divorce wasn’t always hovering in the back of my mind. That’s why I’m writing to you today. I want to ask my fiancée for a prenup before we get married and I don’t know how to bring it up.

I’m not looking to protect my non-existent assets, I’m not expecting her to cheat on me (or that I would cheat on her) or something and I’m not afraid of her taking everything in the divorce and I’m obviously not expecting us to ever actually need it. What I really want is to make sure that we know how things are going to proceed so that if we do get divorced, it doesn’t become the nightmare that I lived through as a child.

How do I tell my fiancée without making her think I don’t trust her or that I don’t have faith in us or our marriage? Is there a way to bring up a prenup that isn’t insulting or makes her feel bad?

Here Come The Lawyers

DEAR HERE COME THE LAWYERS: This is a tricky needle to thread, HCTL. Pop culture and celebrity gossip have taught us as a society that prenups are the domain of the uber-rich and famous, contracts to either penalize philanderers with various clauses and codicils or protection against gold-diggers who are looking to get rich the “old fashioned” way: marrying someone wealthy and then divorcing them. The constant drum beat of “this is for couples who know this won’t last” has functionally taught us that if you ask for a prenup, then there’s something about the relationship that doesn’t smell right to you but you’re going through with it anyway.

In reality… well, yes, there’re folks who use them this way. But to ordinary people living every day lives, it’s really more accurate to think of them as insurance. Nobody buys home owners insurance or car insurance because they expect their house to burn down or because they are sure that they’re going to drive their car into a tree someday. They do it, hoping that day will never come but knowing that if it does, preparing now will save pain, hardship and inconvenience down the line.

So it is with a prenup and divorce. Divorce laws vary from state to state and they can cause all kinds of headaches if you are going in blind and unexpectedly. A prenup smooths out the process by saying precisely how things will go – Person A gets X, Person B gets Y, you agree in advance how you’ll handle Z. Even if the divorce is reasonably amicable, just the process of trying to divide assets or handle any number of unexpected details can bog things down. I watched a couple go through a very friendly divorce reach the point hair pulling frustration as they tried to navigate issues like dealing with the health insurance paperwork, differences in income and selling their house. Having arrangements laid out in advance may not make things more pleasant, but at least it can make things proceed more smoothly and leave everyone with more spoons to handle the unexpected.

But there is still going to be the initial gut-punch of “don’t you trust me?” or “are you having questions about going through with the wedding?” that are going to be hard to avoid. It’s so deeply ingrained in society that it’s almost reflexive.

So here’s what I’d suggest: use a modified version of the Awkward Conversation to talk about things before you have a lawyer draw one up. Schedule a time with your fiancée to talk about the future together. Lead with what you told me about your parents and their divorce – how ugly it was, how the process made everyone even angrier at each other and how it affected you. Then you make it clear that you don’t expect to get divorced and you are absolutely committed to this marriage, but neither of you can see the future and you want to be prepared if anything does happen.

You might want to frame it as insurance or preparing for disaster: not something you want or expect to happen, but because the world is unpredictable and being prepared minimizes pain in an already painful situation. Tell her that you’re bringing it up now, because planning things out when you’re both in a good headspace and able to discuss it rationally will be far less stressful and acrimonious – a way of being kind to your future selves.

Let her know how during your parents’ divorce, you watched the love your parents still had curdle into anger and bitterness and how you never want that to happen between the two of you. Emphasize that, in the event that you do decide to end the marriage, what you want is a road map and checklist of what is going to happen and how. You want things to be as smooth and pre-planned as possible so that it will be as conflict free as you can manage it.

Make it clear that you’re not worried that she’s going to try to take your stuff or that you’re trying to penalize her, just that you believe that by planning things out in advance, you will minimize the likelihood that the process of getting a divorce will make things worse and having this in place will make it easier for the two of you to have as positive a relationship as possible afterwards.

Then, when you’re done, you give her space to react. She may well have a whole host of very large, very loud emotions in the moment. Let her have them. She may have a metric f--kton of questions; let her ask them and answer them as best you can, and as calmly as you can. If she starts throwing accusations, do your best to take a deep breath and let them wash over you, recognizing that it’s more the shock of the moment than what she actually feels. Then, when she’s ready, let her say her piece.

And who knows? Your worries are understandable, but she very well may be on the same page as you. Considering the age we live in, she may not see getting a prenup as a sign of distrust, but as sensible planning. Depending on whether her parents are still married, or if either of them had gone through a divorce previously, she may have similar experiences or stories to yours. So while it’s good to be ready for her being upset, she very well may surprise you.

One more thing that will help: emphasize that you want her to have her own lawyer go over whatever gets drawn up. Making sure that she has her own advocate, independent of you, to look out for her best interests, may help her see that you’re coming to this in good faith, rather than out of suspicion.

It’s a tricky conversation and I don’t envy you having to have it. But if you get through it together, it will be one more moment where something that could have pulled you apart has only brought you even more firmly together as members of the same team.

Good luck.

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