Differential diagnosis of loveshyness

In my life coaching practice, I see a lot of male clients who have trouble getting dates (including fairly severe trouble, such as never having been kissed in spite of being in their thirties). Here is the differential diagnosis I use, in case it is helpful for others in diagnosing the cause of their own trouble getting dates. While I’m assuming a straight man here, some of the advice might be useful to people of other genders or sexual orientations.

(Of course, several may be true at once.)

Lack of Opportunity or Scripts

Some men haven’t gotten dates because they have never put any concerted effort into getting dates. A central example of a Lack of Opportunity case is a man with very success-oriented parents¹ who taught him to concentrate on winning math contests and getting a perfect SAT score, and then a wife would spontaneously appear when he was in his late twenties. Similarly, a man who recently deconverted from conservative Christianity might be a Lack of Opportunity case. And some men, without any particular reason to do so, simply failed to prioritize dating until relatively late in life.

Because he didn’t get in practice dating during his teenage or college years, a man with this problem doesn’t know how to date. He is mystified by how to use a dating site, what to do on a first date, or how you tell if a woman wants you to kiss her. He benefits from learning basic scripts, in the same way a novice cook benefits from following a recipe. An experienced cook can taste the soup and figure out through vibes if the lentils are undercooked or it needs some salt; a novice cook needs “one teaspoon salt, simmer for 45 minutes.” Models: Attract Women Through Honesty is a good source of basic scripts.

Excessive Pickiness

I think this is overplayed by The Discourse because it’s fun to own men by going “you SAY you have trouble dating, but ACTUALLY you’re rejecting all women who aren’t 22-year-old blonde virgins with breasts the size of their heads and a fetish for anal.”

Nevertheless, it is sometimes the case that men have trouble dating because they have unreasonable expectations about what kind of person they’ll be able to date. Sometimes this is an X-style “I want a woman half my age and half my BMI.” But even less dunkable men can have this problem. For example, you might have two preferences that are individually reasonable but unlikely to show up together: a Catholic rationalist; a very ambitious person who wants to play video games with you all day.

A problem I’ve seen a lot is that someone has a lot of really cool friends whom they love spending time with and none of whom they want to date. So they don’t feel motivated to go on dates, because the average person they go on a date with is less cool than their friends. I’m not saying that you should date someone less cool than your friends. But in order to find that equally cool person, you’re going to have to spend many hours with people less cool than your friends—and getting the motivation to do that is hard.

Lack of Attractiveness

To put it very bluntly, some men have trouble dating because they are, in a holistic sense, not very attractive to the average woman.

Here are some things I consider:

• Are you very fat? Do you have bad acne? Is your hygiene bad? Do you have an unflattering haircut? Do you wear dull clothing that doesn’t fit very well?

• Are you broke and chronically unemployed?

• Are you friendless and unpopular?

• Are you unpleasant to be around (subtype boring)? Are you serious all the time and never crack jokes? Do you never venture an opinion about anything more controversial than flowers being pretty? Do you go home from work and watch TV all night and every weekend? Are you super fucking depressed?

• Are you unpleasant to be around (subtype mean)? Do you say nasty things about other people? Are you rude to the waiter? Are you judgmental of others?

• Conversely, are you a wimpy suckup people-pleaser who lets everyone walk all over you?

Now, you might not want or be able to change some of these things. You might be going “gee, thanks, Ozy, I’m supposed to have money and not be depressed? I had no fucking idea.” For many people, losing weight is difficult to impossible. You might think that caring about fashion is shallow, or be extremely introverted, or genuinely feel fulfilled by your TV-centric life. And I left out some aspects of attraction, which are entirely out of your control: while a short, visibly disabled, Asian man is going to have a much harder time finding a girlfriend, you can’t make yourself taller, able-bodied, or white.

Fortunately, it’s possible to compensate. We’re not looking for perfection here. We’re looking for good enough. For example, if you’re fat, you can try dressing in an interesting and stylish way with clothes that flatter your body; this usually works better than dressing to keep people from looking at you or noticing that you’re fat.

If you have an unavoidable weakness in one area, try to hone others. If you’re broke, strive to be handsome. If you’re committed to your unflattering haircut, strive to be kind. If you’re mean, strive to be really really funny.

As you can observe by walking outside, normal men get girlfriends all the time. As long as you’re not holding out for Sydney Sweeney, being an average or even somewhat below-average man is perfectly sufficient to get a girlfriend. But if you are well below average, getting yourself up to average will do wonders for your dating life.

A warning: A lot of men who have trouble dating believe they’re unattractive, but are actually perfectly attractive and sometimes quite hot. Before embarking on a program of self-improvement, consider whether your problem is—

Internalized Desexualization

This is by far the most common problem I observe in my life coaching practice.

I don’t love the phrase “internalized desexualization”, because I worry that that overemphasizes the sex aspect when in reality romance is as much or more of the problem. In essence, men who struggle with internalized desexualization believe some combination of the following (exact specifics dependent on the man):

• My sexual and romantic desires are cringe, pathetic, and embarrassing.

• My sexual or romantic interest is a burden upon others. No one could possibly want me to be sexually or romantically interested in them.

• It is delusional to expect that I will ever fulfill any of my sexual or romantic desires.

• If someone is romantically or sexually interested in me, this is random luck or a blessing from God, which cannot be expected to repeat and which my actions have no influence over.

• I should build a wall which rigidly separates my romantic and sexual interests from the rest of my life. I should never allow any hint of my sexual or romantic desires to bleed over into my normal life.

These beliefs are bad for your dating prospects in a number of different ways.

First, these beliefs are not very attractive. Most women (and men) think it’s hot when someone is genuinely romantically/sexually interested in them. Most women (and men) also think it’s hot for people to have a certain “sexual energy,” to seem like the kind of person who fucks.² But internalized desexualization instead makes you come off as entirely sexless, which is not attractive.

Second, these beliefs keep you from flirting. If you believe that flirting will never result in a relationship, that flirting with a woman is always annoying and burdening her, and that you should hide your sexual and romantic desires from others, you’re not going to flirt with women. Obviously. Why would you cause yourself anxiety, and some woman trouble and pain, for no benefit?

Third, if you do flirt, these beliefs make your flirtation more likely to come off as incongruent and awkward. If you act that everything is very normal and you’re supposed to be doing exactly what you’re doing, people will tend to assume that indeed everything is very normal and you’re supposed to be doing exactly what you’re doing. This is useful advice for organizing social events, getting refunds, and vaping on airplanes.³ It is also useful advice for flirting.

On the other hand, if you’re acting like you’re doing something wrong, people will tend to assume that you’re doing something wrong. If you act like hitting on a woman is as embarrassing and shocking a norm violation as shitting on the floor, women will feel as awkward and uncomfortable as if you were shitting on the floor.

I realize this is an irritating feature of human social norms, especially for us autists who want the rules to be consistent and universally applicable. But as best as I can figure it’s true. Acting like you’re making someone uncomfortable can by itself make them feel uncomfortable.

Fourth, these beliefs make you miss women’s indicators of interest. Unfortunately, when straight women express interest in men, it’s usually pretty subtle. I agree this is annoying and I too wish they would be more direct. But if a woman is romantically interested in you, she’s very unlikely to say “I have a crush on you and I want to go on a date.” She’s more likely to stand near you, to make excuses to spend time with you, to touch you lightly on the arm, to compliment you, to laugh enthusiastically at all your jokes, to make lingering eye contact, or to get dressed up nicely whenever she knows that she’s going to run into you.

If you have a reasonable level of Theory of Mind, you can usually figure out whether a woman is interested in you, at least enough that if she turns you down she’ll be polite about it and you’ll still be friends afterward. But no matter how good your Theory of Mind is, you’re not going to pick up on anything more subtle than “I want to go on a date” if your assumption is that it’s ridiculous and impossible for anyone to be interested in you.

Fifth, these beliefs make you send indicators of disinterest. If a straight woman has made a somewhat blatant indication of interest—she’s put her head on your shoulder, or given you her contact information, or asked you to a movie—you might freak the fuck out, because a woman being interested in you is an impossibility, a violation of the previous laws of social interaction and perhaps reality. You feel scared, worried you’re going to screw it up. Maybe you get avoidant of the entire situation.

But a woman can’t read your mind to discover why you look freaked out, uncomfortable, and avoidant. From her perspective, the most likely scenario is that you aren’t interested in her and she accidentally pushed your boundaries. She’ll pull back and stop expressing interest in you—the same way you would if you asked someone out and they seemed uncomfortable.

Unfortunately, internalized desexualization creates a self-perpetuating cycle. I want to emphasize that these men don’t have an irrational belief that no one is attracted to them. They have the completely rational belief that no one is attracted to them, backed up by an entire lifetime of experience. It’s just that their life experiences are caused by their beliefs.

I think the best solution to internalized desexualization is something like exposure therapy. The man should do some social activity in which he displays the sexual or romantic aspects of himself in some low-stakes and minimally intimidating way. When nothing bad happens, he will be more comfortable with integrating his sexuality with the rest of himself and displaying his sexuality to others.⁴ Over time, we replace the vicious cycle with a virtuous cycle.

But how can a man who has desexualized himself find safe, low-stakes ways to display his sexuality?

By far the most popular way among my clients is going on dating sites. Dating sites have a number of advantages for combating internalized desexualization. Every woman on a dating site has opted in to receiving sexual/romantic attention. You can practice whenever you have a bit of spare time. Sending a message can be less scary than talking to a woman in person. And being on a dating site is very directly related to the goal of having a girlfriend, while e.g. taking up social dance is more indirect.

Similarly, some men might want to go to speed dating events or other events where you met women who are interested in dating. While somewhat more intimidating than dating sites, speed dating can allow you to practice face-to-face flirtatious interaction.

Sometimes seeing a sex worker can help (although I obviously can’t recommend illegal activities in my life coaching practice). Many men feel more comfortable expressing their sexuality with sex workers, who won’t reject them. But I think “I am so unwanted I have to pay someone to have sex with me” can be corrosive in the long run, so do this with caution.

Some social activities offer the opportunity to display your sexuality. Unfortunately, most such communities are limited to people with very specific preferences most men don’t share. If a man is queer or interested in trans women, he can use Grindr. If a man is kinky, he can go to his local munch, nonsexual meetups for kinky people; munches are surprisingly welcoming environments full of nerds and programmers. Men who share the tastes of AO3 readers can participate in shipping-heavy fandom (though not liking slash limits your options somewhat). Similarly, men who are furries can participate in furry fandom. If a man has a lot of money to dump on solving the problem, I’ve heard good things about Slutcon.

Probably the most generally applicable piece of advice is taking up one of the sexier forms of social dance. A friend who does social dance recommends Latin and blues/fusion/micro. Social dance lets you practice touching women, asking for a sensual interaction with a woman, being rejected without hating yourself, and communicating through subtext.

1. Stereotypically, immigrants.

2. This is one of the things people mean when they say confidence is sexy.

3. Thing of Things does not endorse vaping on airplanes.

4. A common misunderstanding is that internalized desexualization can be combated by observing women being horny for other men, or men within the man’s relevant demographics. While that might be helpful for some men, in general the problem isn’t the theoretical abstract knowledge that some women are attracted to men; the problem is the direct, lived reality that no women seem to be attracted to you. The only solution is for the man himself to have low-stakes interactions.