The odds are good and the goods are great

I stole the title and thesis of this post from the great etirabys and arguably I should just link her post. But I have been linking people her post for FIVE FUCKING YEARS and the dating market inefficiency under discussion still exists. So I have decided to write my own contribution to the discourse in the hope that it will finally cause straight women to act in their enlightened self-interest.

Consider, if you will, all the traits you want in a man that other women also want. Funny. Emotionally mature. Willing to do his fair share of the chores. Handsome. Buff. Rich. Tall. Fantastic at sex. Kind. Intelligent. Interesting. Ambitious. Good at music or dancing. Famous????? Wants children. Doesn’t want children. Willing to commit. Hopelessly devoted to you, eager to please, and willing to walk five hundred miles and walk five hundred more just to be the man who walked a thousand miles to fall down at your door.

It is possible to get a man with far more of those traits than you would normally be able to get with your flat ass, spotty employment history, stressful emotional problems, and indifference to wearing makeup.

This is because a large population of objectively attractive men simply won’t put any concerted effort into getting dates. Some of these men are chronically loveshy and have very little romantic experience; others have dated in the past, but are currently going through a sexually unsuccessful period. Many objectively attractive men are single for no other reason than that they won’t hit on women, and you can date well out of your league if you ask them out.

(I would advise that men who have trouble dating consider whether to read this post-- I am going to be blunt and somewhat objectifying about men who have trouble dating, and I don’t want to make you guys feel bad.)

Why This Happens

What? How does this happen? That sounds fake.

In my experience (both personally and when I was a life coach), men don’t put any effort into dating for several different reasons.

Some men are simply too busy to actively date. They have an active social life, a demanding job, or enriching and absorbing hobbies. They’d make time for a real girlfriend, but they don’t feel like they have time to waste sending insipid messages on Bumble.

Some men dislike dating apps. At present, dating occurs overwhelmingly on The Apps. Dating apps tend to emphasize pictures, leaving viewers with only a few sentences of text to get to know the person behind the profile. Dating apps are a particularly bad fit for men who don’t care much about physical appearance and who are primarily attracted to women based on their personalities. I have known many men to object to my advice that they should use The Apps because they literally don’t know how to tell if a woman is attractive from a picture (and at least one man to claim he needs to first read 10,000 words of her blog posts).

Relatedly, some men do poorly on dating apps. This is the flip side of the previous problem. Dating apps reward tall men with attractive faces who photograph well. But most women tend to weight other traits more highly—charisma, sense of humor, talents, intelligence, kindness. Most women wouldn’t actually reject a charming, funny man who happens to be 5’10”. But these men can have a frustrating time on the dating apps—sending out messages that no one ever responds to, spending hours swiping without a date to show for it—and often wind up quitting.

Some men have never really had the opportunity to date. They may have been focusing on their careers or studies. They may have grown up in a conservative religious group and deconverted. They may have had success-focused (stereotypically, immigrant) parents who strongly discouraged dating and socializing. They may have had male-dominated hobbies and a male-dominated friend group that left them with no opportunity to meet women. They might have undergone some personal tragedy, such as the death of a loved one or a chronic illness. It is often possible to snap up these men before they enter the dating pool.

Some men never learned how to date. They’re mystified by how to flirt, tell if a woman is interested in them, ask women out, plan a date, or figure out when to kiss her. Because the process of dating seems mysterious and incomprehensible—not to mention full of landmines where you accidentally sexually harass someone—they avoid dating.

Some men experience internalized desexualization—the belief that your sexual and romantic desires are cringe, pathetic, and burdensome on others, and it is delusional to expect to fulfill them. Naturally, these men don’t put any effort into dating. Why would you waste time on dating if no one would ever be attracted to you? Surely the selfless approach is to hide forever his deepest, darkest, most shameful secret—that he would really like to hold a woman’s hand.

Of course, many men avoid dating for multiple reasons. If a man is already quite busy, then he’s unlikely to want to message women on The Apps at random in the hope that one of them turns out to have an intriguing personality. Men who never had the opportunity to date often don’t learn how to date, so once they have a chance they don’t know what to do. Lack of success on dating apps can feed into internalized desexualization. Etc.

These problems aren’t more common among men than among women. But pretty women are much more likely than men to be asked out, even if they put zero effort into dating. They might have fewer choices than if they put any effort into dating, but there is a reasonable chance that they’ll manage to date someone.

But because straight women don’t ask men out, a man who doesn’t put any effort into dating simply won’t get any dates—even if he is otherwise a desirable boyfriend or husband. (Women who aren’t pretty and don’t put any effort into dating are in a similar position to men here.)

Are you saying that these men are so niiiiiiiiiiice I should give them a chaaaaaaaance?

Absolutely not.

I feel bad for kind but generally unattractive men, but I’m not going to write a whole long post trying to convince you to date them; that’s not good for you or them. What drove me to write is the number of chronically single men I’ve run into who are objectively really good romantic partners—cute, fun to be around, smart, interesting, kind, generous, emotionally mature, and prepared to endlessly dote on their hypothetical girlfriend that they don’t have. “Kind but unattractive people can’t get dates” is sad, but an inevitable feature of human mating preferences. “Kind, interesting, handsome, funny, emotionally mature people can’t get dates” is PERVERSE. I refuse to believe that we can’t do better.

I believe the correct approach to asking men out is a little healthy self-indulgence, like opening a box of chocolates and considering whether you’re more in the mood for almond or coconut today. Ask out the hottest guy in the room! Ask out the guy with the most adventurous life! Ask out the guy you start talking to and then suddenly it’s six hours later and you’ve been ignoring everyone else at the party and they’re all annoyed with you! Ask out your favorite Internet microcelebrity!

Don’t ask a man out unless you’re actively excited about the prospect of going on a date with him. (Not necessarily about getting married to him and having six babies, but about the prospect of spending an evening in his company.) This is a matter of time management. Once you’ve unlocked the secret of asking men out, if you have low standards, you could easily have four dates a week and no time to knit while listening to romantasy audiobooks.

Now, of course many of the traits that make men not put much effort into dating are themselves not very attractive. Most women are more attracted to smooth, confident flirts. A lot of women are going to be hesitant to date a man with issues about his romantic and sexual desires. Many women find being asked out itself attractive. And of course “dating apps emphasize physical attractiveness at the expense of other desirable traits” is irrelevant to you if you are primarily attracted to men with strong jaws and six packs (although you might still want to ask out gymcels).

But right now the dating market overweights those traits, relative to how much they matter for your long-term relationship happiness. Even if a man is romantically inexperienced, by the time you’ve been dating for a year, he’ll have exactly as much experience as any other man in dating you. An emotionally healthy man with internalized desexualization feels that way because he has never experienced a woman being attracted to him; if you show him that you’re attracted to him, he’ll believe it! And when you’re happily married, you’re just not going to care that much who asked whom out or whether the first date was kinda awkward.

I also want to point out some advantages of loveshy or romantically inexperienced men.

First, being the object of ten or twenty years of repressed sexual and romantic desire is both romantic and extremely hot. The sheer force of some loveshy men’s unleashed passion is indescribable. Not just sexually—although, yes, sexually—they are just so thrilled to be able to hold you and celebrate Valentine’s with you and tell you you’re beautiful and and and.

Relatedly, I’ve found that people who have spent years on the apps often wind up cynical, jaded, and prone to viewing all dating as a war between men and women. Many loveshy or inexperienced men, conversely, are earnest in a way that I almost want to describe as innocent. (Probably best to avoid ones who read dating discourse on X, which is the worst of both worlds.)

Second, as I have written before, the one of the most important factors in relationship happiness is having a delusionally positive view of how great your partner is. Loveshy or inexperienced men are far more likely to have a delusionally positive view of you, because as far as they know you’re irreplaceable, you saved them from a life of loneliness, and no one else has ever wanted them the way you do.

I think those men should ask me out.

I also think those men should ask you out but they keep not listening to me so now I am trying to address the other half of the problem.

Common Concerns

I would like a 6’ man who benchpresses twice his own bodyweight, earns six figures, is as emotionally mature as Gandhi, and has a giant cock. Will asking men out allow me to reach my goals?

I am not a miracle worker.

Taking advantage of this market failure will allow you to date somewhat above your “league” and to have an abundance of potential sexual/romantic partners. But very few men are the hero of a contemporary romance novel. Even if such men refuse to put any effort into dating, they will likely get scooped up by some other woman who has discovered the trick of asking men out. And you would have to meet hundreds of inadequate men before you find the Fitzwilliam Darcy of your dreams.

Consider seriously what is important to you and what isn’t. You might end up with a man with six pack abs who’s short, or a rich man with some interesting neurodivergences, or a tall man who can make up with certain inadequacies using his fingers.

In general, you will have an easier time with some preferences than others. Within my own niche, high IQ is basically free, while wealth and notable career success are not much harder. However, if you’re looking for muscles or a good fashion sense or a face that doesn’t look kinda dorky, you may end up having to compromise on other traits you would find desirable. (Some women I know have had very good outcomes through choosing men who are open to dressing well, and then buying all their clothes for them.)

If nothing will shift you from your desire for Buff Rich Big Dick Gandhi, I recommend trying to meet lots of men who don’t put much effort into dating, in order to maximize your chance of stumbling across such a person.

If he doesn’t put any effort into finding a partner, wouldn’t he not put any effort into me once we’re dating?

You know, you would think that’s true, but in my experience it’s really not.

Dating is stressful and horrible for many people. Talking to people on dating sites and going on first dates with strangers are the most excruciatingly awkward experiences our species has yet invented. Asking out people you know is terrifying. Getting rejected makes you feel like you’re about three inches tall. Very often, you put in a lot of effort and get nothing in return but a bunch of “I had a nice time, but I’m not feeling it” messages (if they don’t outright ghost you).

On the other hand, actually being in a relationship is fun. You get to do things like have sex and talk about your days and give each other emotional support and participate in each other’s hobbies and make sickeningly cute faces at each other while your friends all want to vomit. You can also more easily combine dating with other activities you want to do: you and your girlfriend can cook or go to parties or watch movies together, but none of these activities combine well with swiping on Tinder.

Many men are more interested in spending fun, fulfilling time with a woman they love than they are in doing a boring, soul-crushing activity with no obvious benefit.

I’m worried these men are misogynist or sexually entitled.

It is important to be aware that some men are loveshy because they are appalling misogynists and therefore no women want to date them. However, these men are easy to identify—if every other woman he’s ever met has figured out he’s an appalling misogynist, you can too.

In general, men who refuse to put any effort into dating have the same range of opinions about women as any other men: some are feminists, some are opposed to sexism but have various objections to modern feminism, some are decent people but have never really thought about gender issues, some believe strongly in gender norms and stereotypes, and some hate women. You should, of course, be actively screening for incompatible values and for general weirdness about women, but there is no need to take any unusual precautions in this regard.

Similarly, you should of course be alert to signs of sexual entitlement from any man when dating, but if anything the men we’re targeting are less likely than normal men to be sexually entitled. Men who experience internalized desexualization assume their sexual desire is unwanted and bothersome, and they don’t want to annoy any women by flirting with them, which is the opposite of sexual entitlement. In my experience, they often find women with clear boundaries reassuring—they know they’re not going to harm you by accident.

Be aware that some romantically inexperienced men have developed confused ideas of how dating works from some combination of social media, TV shows, and books. Some of these are obviously innocuous (e.g. Disneyfied “love at first sight”) but some can sound like red pill material (e.g. “women are only attracted to men who are taller than 6 feet”). Pay attention to whether he seems resentful of women or just (for example) sad about his own height. If his ideas seem more mistaken than hateful, and he’s willing to be corrected, I wouldn’t worry about it.

I’m worried that men who don’t ask me out don’t really like me.

I think this is the most common reason (besides “asking people out sucks for everyone”) that women don’t ask men out, and I understand the concern here. People are far, far, far more likely to say “yes” to a date than they are to ask the same person out. Saying “yes” is way less scary; if someone is interested in you, you often want to give them a chance, even if you’re not necessarily crushing on them right now. Many women don’t want to date someone who is giving them a chance. There’s a certain sense that “if he wanted to, he would.” Men are supposed to ask women out. If he doesn’t ask you out, he must not be attracted to you. And—especially if a man doesn’t have a lot of options—there’s a real risk he’ll slide into a relationship with you because it’s easy and better than being alone, even though he isn’t in love with you.

However, whether someone asks you out is only one piece of evidence about how much they like you, and it’s not even that good as evidence.

Imagine two men. Aaron crushes on a girl for six months before he finally works up the nerve to ask her out; since it takes a while for him to meet women he has a crush on, he asks out about one woman a year. Bob asks out any woman he is passingly attracted to, so he asks out one woman a week. If your social group is composed equally of Aarons and Bobs, you are literally forty-nine times more likely to be asked out by Bob than Aaron.

Now, this is an extreme case, and Bobs are actually quite rare. But the point stands that whether a man asks you out is evidence both about whether he is unusually interested in you and about whether he has read the Asking People Out Manifesto. Depending on how many Bobs are in your friend group, asking men out may even cause you to date men who are more attracted to you than you would date if you waited to be asked out.

Whether you asked a man out or the man asked you out, you should pay attention to all the information you have about whether he likes you. For example, how quickly does he respond to texts? Does he initiate text conversations? Does he make plans with you? Does he do things to make you happy? Does he do things to make you happy that are unusual for him, that he wouldn’t do for any random friend of his? Does he do things that are inconvenient for him to spend time with you or to make you happy? Is he affectionate (cuddles, kisses, compliments, sweet nothings)? Does he talk about your shared future together (whether that means talking about your future kids or planning a trip six months from now)? Does he make life plans with space for you? Does talking to him make you feel small, or humiliated, or like he wishes a Yeerk would enter your ear and make you a completely different person with the same face?

People will tell you whether they like you if you listen and pay attention. Most of the time, when you date someone who doesn’t really like you, the problem isn’t that they are failing to communicate; the problem is that you are doing wishful thinking. And wishful thinking is a problem whether or not the man asked you out.

I’m only attracted to assertive, dominant, extroverted men.

I will admit that my advice here works better if you are interested in men who are rather shy and passive, or at least don’t view shyness and passivity as a dealbreaker.

That said, there are extroverted, assertive, dominant men who are weirdly bad at putting effort into dating. Some men are extroverted in general but struggle to ask women out. Similarly, some men are assertive and dominant with other men or at work or while doing their hobbies, and are only passive in dating. With good partner selection, you can totally ask a man out and later find yourself hanging off his arm while a circle of supplicants waits breathlessly for his latest drop of wisdom, if that’s your kink.

If you have this set of preferences, and can see your way to being fine with handholding a man through the first few dates, I recommend having it as an adjunct strategy. Primarily choose to date men who ask you out, but if you encounter an assertive, dominant, extroverted man who happens to be single and not to notice any of your subtler flirtations, consider being direct.

I’m only attracted to men who make the first move.

Then don’t take my advice in this post. If you’re just not attracted to something, no one can argue you into being attracted to it.

That said, consider sending this advice to your friends, so that they ask people out, get into happy relationships, and leave more of the men willing to ask people out for you.

Target Audience

What kind of women should take this advice?

Some women will benefit more than others from taking advantage of this market inefficiency.

Of course, the more you’re attracted to the kind of men who refuse to put any effort into dating, the more useful this advice is. In particular, if you are particularly attracted to men who are passive, shy, adorably nervous and awkward, or undergoing a sexual awakening, and you don’t ask men out, you are an idiot.¹

Within my own niche, I would recommend it highly to women who value men being intelligent, curious, well-read, and interesting. If your ideal date involves spending hours talking about history, programming, or the books you’ve been reading, you ought to ask men out.

If you are interested in High Status Men (TM), asking men out is a better idea if your idea of an extremely attractive high status man is “Nebula Award winner” or “multimillionaire because he was an early employee at a unicorn startup,” and a worse idea if your idea of an extremely attractive high status man is “professional basketball player” or “elected politician.” My advice is entirely useless if your idea of an extremely attractive high status man is “club promoter.”

Dating apps and “wait around until someone asks me out” both tend to advantage thin, feminine, conventionally attractive women, because (as discussed earlier) they both tend to weight easily visible traits like physical attractiveness over harder-to-see traits like kindness, intelligence, or emotional maturity. If you are plain, fat, or uninterested in doing beauty work, you will likely do better if you ask men out and then win them over with your charming personality.

I have asked a lot of men who refuse to put effort into dating to bluntly describe their sexual preferences to me, so I can help them get dates. From this, I have drawn the conclusion that these men tend not to care much about physical appearance, and tend to care more about personality and interests. You will likely do better if you are full of wonder about the world, like thinking about things, and have unusual hobbies. Female-dominated hobbies like fiber arts, baking, or writing fanfiction are terrible for meeting men, but work fine for this purpose.

Loveshy women will do better if they ask men out. I realize that this is difficult advice for loveshy women to put into practice—it is terrifying to ask people out, especially if you have little to no evidence that anyone has ever found you attractive—but I will walk you through how to do it in a later section. Loveshy people often make great matches for each other, but you will only be able to match each other if one of you does the asking!

Masculine or butch straight women definitely benefit from asking men out, although in this case it isn’t primarily because they’re taking advantage of the market inefficiency. Straight men who prefer masculine or butch women love it when a woman is direct, assertive, and sexually aggressive. Plus it is probably your natural style.

I’m a trans woman or nonbinary person assigned male at birth. Will this advice work for me?

Probably, yes.²

If you haven’t transitioned or are very early-transition, or your community tends to not be accepting of trans people, you should hesitate about hitting on straight cis men. You aren’t very likely to succeed, and you might provoke a man into a gay crisis, which could be humiliating for you and even potentially dangerous.

However, if people around you generally seem to treat trans women as women, and you are reasonably passable, I would urge you to ask out straight cis men you find attractive. Many more straight cis men than you think are open to transfeminine people. Many straight cis men are more interested in breasts, hips, soft skin, feminine facial features, and so on than they are in the vulva per se. In my experience, straight cis men who don’t put much effort into dating tend to be more flexible about cis/trans status—maybe because they tend to care less about physical appearance, or maybe because they tend to be motivated to get over the subconscious homophobia and cissexism that keeps many men from acknowledging their attraction to trans women.

In general, in trans-accepting environments, straight cis men who aren’t attracted to trans women aren’t going to hatecrime you. Indeed, they are most likely to feel uncomfortable about rejecting you, because they’re worried about hurting your feelings or accidentally misgendering you or making you feel unattractive. Be prepared for this; see “what happens if he rejects me?” below.

When dating straight cis men who aren’t chasers, you will generally have a better time if you don’t necessarily want to use your penis during sex (for example, because it makes you dysphoric). Even a lot of straight cis men who are attracted to trans women will never be the world’s biggest fans of penises. (If you have bottom surgery, of course, this makes the entire problem a nonissue.)

I know you girls are going to obsess about your incredibly male brow ridges or jawlines or midfaces or whatever.³ If strangers sometimes spontaneously call you “she” or “ma’am”, you are reasonably passable for these purposes and should feel free to hit on men whom you find attractive.

(Many of these men are also willing to date nonbinary people assigned female at birth, or early-transition/nontransitioning trans men. Similar considerations apply, although it’s worth watching out for signs that he sees you as a woman, which is not the recipe for long-term relationship satisfaction.)

How To Date Men Who Don’t Put Much Effort Into Dating

How do I find these men?

You will have very bad luck finding them on dating sites. Going on a dating site is putting concerted effort into dating, which is precisely what these men don’t do. Most of them have installed a dating app at some point, but they rarely messaged anyone and then promptly gave up. You have a low chance of catching one of them in the two months per half-decade they actually have the app installed.

Instead, you need to find them in your social circle. You may, especially if you’re a frequent reader of Thing of Things, already know many of these men! If your social circle is more than 60% male and many of these men appear mysteriously girlfriendless, consider the possibility that many of these men would quite like a girlfriend if one fell into their laps, and perhaps the person who falls into their laps can be you.

My personal experiences are mostly about a specific demographic of these men. Signs that your social circle also contains a concentration of them:

• You live in a “tech hub” (the San Francisco Bay Area, Seattle, Boston).

• Many of your friends are programmers, quant traders, STEM grad students, scientists, or people who work any job in which “working in industry” is a useful distinction as opposed to a tautology.

• You’re into the kind of tabletop RPGs played by straight men, not the kind of tabletop RPGs played by queer people.

• Anyone you know has or is working towards a PhD in physics.

• Anyone you know has ever fondly reminisced about Mathcamp.

• You are an effective altruist or rationalist (small portion of the population, large portion of my readers).

However, I suspect that this is more a reflection of my friends and blog readership, and less representative of all men who refuse to put effort into dating. I eagerly anticipate field reports from women about their own dating experiences with diverse groups of men who don’t put any effort into dating.

You might want to take my advice, but not have a concentration of these men in your social circle. In this case, I recommend getting into a “programmer hobby”: tabletop RPGs, board games, chess, Magic: the Gathering, speedcubing, writing science fiction or trashy webnovels, Ultimate Frisbee, rock climbing, Brazilian jiu jitsu, or anything you do at a makerspace. Running or cycling clubs are good if you’re in a tech hub but not otherwise. While Burning Man and social dance are both programmer hobbies, your odds are worse in these cases, because Burners and dancers are more likely to be comfortable with hitting on women. Again, this only reflects my own experiences; I hope people with other recommendations leave a comment.

A common mistake is to try to figure out whether a man struggles to ask women out before you hit on him. Once you have already determined that your social group has enough men who struggle to ask women out that this is a reasonable strategy, don’t bother obsessing over the prospects of any individual man. You will likely mistakenly assume that this man is so attractive that he must have gotten dates in the past, and therefore psych yourself out. Besides, even the men in these demographics who do get asked out tend to find being asked out a pleasant surprise, and to be kind and gracious about it.

How do I date these men?

You must ask them out.

There is no other way around it. These men are single because, for whatever reason, they won’t ask women out. The secret ingredient—the thing that lets you get these men when other women don’t—is that you are willing to ask them out yourself.

A common mistake women make is to look for the man to be flirtatious, or to show what pickup artists used to call ‘indicators of interest.’ Our target men will never do this, because they’re nervous and uncomfortable around women they’re attracted to, or because they’re concerned that even the mildest flirting is a form of sexual harassment. Look for general signs that a man likes you as a person—making an effort to talk to you at parties or social events, doing small favors for you, laughing at your jokes, the ordinary things that make you say “oh, this person wants to be my friend.” Don’t look for compliments, unusual levels of touch, strong eye contact, or anything else you would normally take as flirting.

Only ask a man out if you actively want to go on a date with him. If you’re unsure whether you want to go on a date with him, keep talking to him at parties or social events until you’re sure you’re up for at least a first date. If you want to go on a first date to get to know him, but aren’t sure whether you’d want a second, that’s fine.

Using some pretext, obtain the man’s contact information or get him alone. If you are struggling to think of a good pretext, “I’ve enjoyed our conversation, can I have your email/Discord?” and “it’s loud in here, want to go for a walk?” both work fine. Never ask a man out in front of other people—it will freak him out and make him feel pressured.

Then, say some sort of brief compliment. Ideally, choose something you like about him: “our conversation yesterday about the Roman Empire was the highlight of my night.” If you can’t think of anything, a vague “I like you” or “I enjoyed spending time with you” is fine. There are multiple schools of thought on whether to include “you’re cute” or similar. On the one hand, these men will completely miss any indicator of sexual interest more subtle than “you’re cute,” and including a “you’re cute” can simplify matters later in the date. On the other hand, if you’re unsure whether you’ll find the man appealing, leaving out the “you’re cute” allows you to retroactively make the hangout platonic seamlessly and without awkwardness.

Then, say “I would like to go out with you sometime.” In my experience, it is usually best to plan the date yourself according to your own preferences: say “let’s get coffee” or “I want to go see $movie” or “let’s go for a hike” or “come over to my place and I’ll make dinner” as you prefer. Choose whatever activity you like most without trying to please him. However, if you’re into the man planning the date, by all means leave it vague and allow him to come up with the activity.

On the date itself, you will need to make your interest clear and unambiguous. Three successful strategies are compliments, touch, and direct communication.

Direct communication is the simplest technique. Simply say “I really like you and I want to [go out on more dates with you]/[be your girlfriend]/[kiss you].” Very likely, only the most assertive and blunt women will want to use this technique, but it is useful if you’re too lazy for the other techniques.

A compliment is similar to the “you’re cute” you might have said while asking him out. Give a nonsexual but unambiguously romantic compliment: “you have a nice smile,” “you have beautiful eyes,” “I love your biceps,” “you’re cute,” whatever. A crass or sexual compliment (“nice ass”) will likely freak him out, while he might miss that a completely platonic compliment (“you’re so smart!”) is intended as flirtation.

If he is interested in you, he will normally return the compliment, often after a period of silence or unrelated conversation in which he is visibly working up the nerve to do so. Don’t be concerned if he repeats your compliment (“you also have a nice smile”). He might not know what kinds of compliments are okay, and is repeating yours because he’s sure that one is all right and not somehow sexual harassment. You can easily teach a man better compliment behavior once you’re dating (I will discuss this in more detail later).

Touch means making romantic physical contact with him. Begin with subtle, plausibly deniable touch, such as touching his shoulder to emphasize a point, hugging him as a greeting, or touching legs with him while you’re sitting on a couch. Observe whether he pulls away or reciprocates the touch. If he’s matching your level of touch, make a more romantic form of physical contact, such as holding hands or putting your head on his shoulder or chest. Again, notice if he reciprocates, pulls away, or escalates the touch himself. For example, if you put your head on his shoulder, he might put his face in your hair or even kiss your head in a matter he imagines is subtle but absolutely is not.

Unfortunately, many men who are inexperienced with women feel scared and uncomfortable when a woman touches them, even if they are very enthusiastic about the touch. So his body language might look like he doesn’t want to be there. If you notice a man has uncomfortable body language but he’s not pulling away, I recommend verbally checking in (”are you okay with cuddling?”).

If he has returned several compliments and/or you’ve been doing romantic physical contact for a reasonable period of time, you can kiss him. I usually find it least awkward to ask “can I kiss you?” but if he’s actually giving positive body language feel free to kiss him spontaneously. I have no personal experience with waiting for a man to kiss me but I imagine it taking for-fucking-ever for him to get brave enough to ask you; up to you.

What happens if he rejects me? I’m nervous.

If you ask men out, they might reject you.

Being rejected is scary and embarrassing for everyone. But remember that men turning you down for dates is a good thing. It means that you don’t wind up dating someone who is meh about the prospect of dating you. If a man isn’t physically attracted to you, has dreamed of nothing but being a dad since he was eight years old while you’re aggressively childfree, or is about to move to a different continent, you don’t want to waste six months on dating him while you find this out.

Many women don’t want to ask men out because they’re worried that men will say ‘yes’ without actually wanting to date them. Every man who rejects you has saved you from that fate.

When asking a man out, try not to think of the goal as getting a date. Think of the goal as letting him know about your feelings. As long as he knows what you feel about him, it’s a success. If you go on a date, it’s a success (date!). If he feels complimented but isn’t interested in you, it’s a success (you made someone you like happy and found out that the two of you aren’t compatible). If he’s an asshole, it’s a success (you have found out that he’s a jerk and won’t have to waste any more time with him).

Men who don’t put any effort into dating know that asking people out sucks. (That’s a major reason they don’t put any effort into dating.) Typically, they will try to reject you kindly, compassionately, and with concern for your feelings. Often, they’ll worry about making you feel unwanted or undesired. In my experience, it’s common for them to specifically reassure you that you’re attractive and that you’ll find someone else soon. In general, they don’t find being asked out annoying or burdensome; they feel happy and flattered that someone is interested in them, even if it’s someone they’re not interested in. Quite often, whether or not they want to date you, you wind up making their day!

Like most scary things, asking men out gets easier with practice. Your first time, you may very well have a panic attack. This is normal. Schedule a phone call or hangout with someone supportive for afterward, queue up some of your favorite TV show, or give yourself an extra dessert. Eventually, it’ll be easy.

What if he doesn’t know what to do while dating me?

Romantically experienced people enter dating with a lot of scripts about what’s supposed to happen when—who plans the date, what you talk about, who pays for the date, when you kiss for the first time, when you become exclusive or committed, when you open up about your pasts or your squishy feelings. Often, even late in the relationship, people rely on cultural scripts to answer questions like “are we allowed to have friends of the same gender?” or “when do we stop using condoms?” or “do we celebrate Valentine’s Day?” or “when do we move in together?”

Romantically inexperienced people don’t have these scripts. If you aren’t prepared, the first dates can wind up clumsy or awkward, because they have no idea what they’re supposed to do. But your partner’s romantic inexperience can also be an advantage for you, because they will tend to defer to you about what the scripts are, which means that the scripts for your relationship can be anything you want them to be.

Now, I am not saying that you should go against a man’s expressed preferences. Obviously, listen to him when he communicates his own needs and boundaries. But if you give obvious directions in early dating, he will tend to find this reassuring because now he has some guidance.

Most of the time, the best technique is to act decisively in accordance with your own preferences. As an example, imagine you don’t feel comfortable kissing on the lips until the third date. Romantically experienced men will usually interpret this preference as a sign that you dislike him or are totally asexual, which creates annoying stress and drama. But if you’re dating a romantically inexperienced man, you can simply kiss him on the cheek at the end of the date and say that you have a lovely time. Don’t apologize or try to explain; act like this is a perfectly normal thing to be doing, exactly what everyone does while dating. He will typically go along with you.

Similarly, if you prefer to split the check, simply take out your card and cover your half. If you think a man should plan the dates, say “what do you want to do next weekend?” If you’re polyamorous, talk about your partners in a calm, matter-of-fact way. If you prefer regular video calls when he’s on a work trip, say “I’m looking forward to your next video call.” The trick is to act like your preferences are the social norm and you expected him to know this all along.

Many women will feel selfish or uncomfortable about being this decisive. This is completely wrong. You are helping him. When you act this way, he feels relieved. Often, the whole reason that he hasn’t dated is that he doesn’t know how, and he’s terrified of making a mistake. Giving him clear scripts is a favor to him, and if you’re going to be doing it anyway, they might as well be whatever scripts you prefer.

You can also model the behavior you want to see from him. Romantically inexperienced men will typically take cues from you about dating. If you (say) make him breakfast in bed, you almost can see him go “oh! People who are dating are supposed to make each other breakfast in bed!” and expect a breakfast in bed next week. Similarly, if you hold hands with him in public, you can expect him to start grabbing your hand when you walk places. If you text him “good morning” every morning, you can expect him to start texting good morning. If you offer tactful constructive criticism about his sexual performance, you can expect him to start offering tactful but constructive criticism about yours.

Unfortunately, modeling only works for behavior that you also want to do, which makes it a bad fit for women with strongly gendered or otherwise nonreciprocal preferences. Men also might overgeneralize (“I should provide tactful constructive criticism about everything!”) or undergeneralize (“she compliments my smile, so I should specifically compliment her smile and not anything else”). But modeling is still a useful technique for your toolkit.

Finally, you can try direct communication. You should be doing this in relationships anyway, but it is particularly useful for relationships with romantically inexperienced people. If you have some preference, simply say it forthrightly, but without being critical: “I’d like it if you told me more about your day,” not passive-aggressive hinting, not “you don’t care about me!”, and not a lengthy tangle of words with so many caveats that he can’t tell what your point is. Often, praising good behavior (“I loved the picnic you planned last weekend!”) is better than criticizing bad behavior (“you never take me out!”). Remember, the poor behavior of a romantically inexperienced man is often ignorance, not malice.

The ability to set the scripts is very powerful. Part of the reason that age-gap relationships often end badly is that, if the older partner implies that people who really love each other have condomless sex or no woman lets her boyfriend have female friends or all men fly into rages, the younger partner has little evidence to the contrary. Experience-gap relationships can fall into the same problems. Feel free to set scripts that you like, but don’t abuse the power to create scripts that exploit him or make him unhappy.

How do I show this guy that I like him?

Many inexperienced men are used to no one being romantically or sexually interested in them, so they struggle to believe that you are interested in them just because you’re “dating them” and “telling them how much you love them” and “enthusiastically expressing your desire to have sex with them.” At best, this can be frustrating. At worst, it can cause serious relationship problems—you wind up not criticizing or disagreeing with him because you don’t want to set off a fit of insecurity, or having to limit your ordinary friendships and activities to keep him from being jealous.

The sine qua non of solving this problem is to only date emotionally mature people who are capable of deriving accurate beliefs like “my girlfriend wants to date me” from available evidence. I recommend this choice.

But you can help boyfriends who are only somewhat emotionally mature work out that you like them. I recommend clear, direct, and unambiguous communication.

By “clear, direct, and unambiguous communication,” I don’t necessarily mean saying “I really like you, want to have sex with you, and am happy to be dating you” (...although that sometimes helps). Instead, think of all the different ways you can communicate affection. Make a romantic playlist! Hold hands with him in public! Cuddle him to sleep! Give him specific, detailed compliments about whichever of his traits that you like! Write him a love letter! Tell other people how great he is in a situation where he can overhear!⁴ Plan dates you think he will like! Give him small presents that made you think of him! Ask thoughtful questions about his interests! Be really enthusiastic in bed! Cook for him! Read his favorite book!

Now, you will need to adjust this based on your individual style and personality. Some people aren’t the PDA type; other people dislike planning dates or being sexually forward. (...I do recommend reading his favorite book regardless.) But the idea is to signal fondness, affection, and appreciation in a way that is impossible to rationalize as you just being a generically nice person.

I understand that being emotionally demonstrative can be difficult for some people. To some people, it can feel vulnerable and embarrassing (“what if he thinks I’m a Stage Five Clinger?”). To other people, it can feel awkward and artificial (“what’s next, I stand below his window with a boombox that plays In Your Eyes?”). But I think the best solution for this kind of relationship insecurity is giving him undeniable evidence that you love him, that he makes you happy, and that you want to be with him.

In conclusion:

• Many objectively attractive men don’t get dates because they won’t ask people out.

• If you ask them out, you can date them.

• Then you get a hot boyfriend.

• Everyone wins.

1. I suspect connoisseurs of this sort are the minority, but if I convince even one straight woman with these preferences to take up asking men out, I will count my entire blogging career a success.

2. Straight cis men reading this who are not attracted to trans women: I am not the Trans Attraction Police. I have no power to force you to date trans women you don’t want to date, nor would I use this power if I could. But no one has a right to not be asked out by people they find unattractive. If you consider the matter, you would realize that “I have a right not to be asked out by people I’m not attracted to” is not in your best interest either. Please chill.

3. Incurably fembrained of you all.

4. I originally learned this technique from a book about parenting toddlers but it works great for relationships with adults too.