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Incredible Dickheads & Where to Find Them: A Review of Books on Picking Up Women

With help from guides by Roosh V's problematic predecessors, it's never too late to find a valentine.
Illustration by Jessica Olah

Long before "neomasculinity blogger" Roosh V terrorized womankind with his self-published How to Date Women from Different Countries book series, men were telling other men how to entrap specific kinds of women into abusive sexual flings or even long-term relationships.

Andrew Dolan's self-published 2008 152-page tract How to Date Older Women brings an equal blend of optimistic delusion and terrible writing. Dolan's premise is straightforward, at least: You broaden your chances whenever you allow mature ladies into your dating pool, and you might even land somebody formerly out of your league. If she got a divorce, "the homecoming queen thus might be back in circulation at thirty-five or forty, and turn out to become a real social possibility for you," writes Dolan.


A great place to spot aging singles is while standing in line at the supermarket, which allows you to smoothly inquire into whatever merchandise she's buying. Notice ice cream in her basket? Be mentally nimble. Mention an ice cream store nearby and offer to visit it together "immediately." If that doesn't work, there'll be other opportunities. Maybe "you see an older woman standing on the street looking around as if she is lost." (This, of course, is common, Dolan says.) Watch her closely from afar until she waves at you. Her signal means you're safe to approach her, explains Dolan. Offer to walk her to her destination, and if she accepts, thoroughly unleash an avalanche of dialogue. "Say anything at all, just don't let the pace of conversation come to a crashingly complete and silent stop," Dolan writes. Carefully memorize any personal facts she volunteers, and after 15 minutes, watch her facial expressions and body language. If she's smiling, she might like you, and "she may even be getting a bit aroused by being around you," writes Dolan.

As it turns out, women paired with younger men win, too, by "experiencing intense sexual thrills." (Dolan teases us often with vaguely sex-related phrases.) To maintain the relationship, avoid showing "any sort of embarrassment about being seen in public with her" that you might have. But be warned, because the outside world can get thorny. Suppose you hear somebody say something you don't like about your relationship's age imbalance. Dolan's recommendation: "Say out loud 'that's the stupidest thing I've ever heard.' Keep repeating this louder and louder each time," into, I presume, infinity.


She may even be getting a bit aroused by being around you.

Older sons living at home are tricky, too. "Maybe you can deal with this, maybe not. Maybe they can deal with this, maybe not," writes Dolan, poorly, before delivering a firm zinger. "If they live in mom's house, they had better get used to adjusting to mom's lifestyle and [the] fact that mom has sexual needs."

If one thing is completely clear throughout, it's that Dolan didn't write so much as a single word in order to seem cool. If you're looking for the opposite, try 1987's How to Date Young Women: For Men over 35. Its author, R. Don Steele, is "trapped" in the body of a 46-year-old, but he's also a "virile male with plenty of miles left on [his] cock." He exclusively dates 18-to-24-year-olds, he says, because he values the resulting symbiotic effects. "She teaches you how to enjoy the now, you teach her how the world really works," he writes. It also helps that younger women are less likely to be "fat, angry ball-busters."

Many eligible bachelorettes in line at the grocery store. Photo via Wikimedia Commons

"Much of the right attitude is your willingness to walk away from her," writes Steele, and this method surely delivers. "There are weeks my dick hurts from so much grand sex," he says. (A later chapter contains Steele's post-boning etiquette tips, including: "For Christ's sake, don't ask her if she came.") Steele describes his numerous pussy harvests in varying detail, such as an encounter with Tina, a 19-year-old. "She fucked [me] four times on the second date. That's right, she fucked me," he says. Here's how he says Janice, a good-looking 20-year-old who "loved to party," initiated her first date with Steele: "I'm ready to fuck my brains out, going crazy. How 'bout Wednesday night?" And when Steele was "somewhat aloof but pleasant" to Mary, a 25-year-old beauty "with an ass that made me cry," things abruptly got steamy: "She was standing in my kitchen with her blouse unbuttoned, her lipstick smeared over both our faces," and she was "rubbing her crotch against my thigh while I caressed those magnificent buns," he writes.

Steele rolls out cogent nuggets of advice. For instance, don't dress old, don't wear glasses, and if your young-bunned beauty sees you in bifocals, forget it. It's "like rolling over to her in a wheelchair with a shawl on." Empathize with her mindset: "think back… remember what an asshole you were at 20." Consider her motivation: "She wants a cock inside her, thrusting." Stay away from nightclubs full of single women. "These dick-of-the-week bar flies are big time disease carriers." When guys date multiple girls, though, it's totally different: "Always have a string at least three young pearls long… The more of them you're working on at once, the less likely you are to come on too strong." And finally, be practical. Forget "big titted girls and beauty queens… Go where the competition is limp, stick with 6.5's to 8.0's, they're better human beings and more fun."

When picking up women, it's always important to keep your goals in mind. Sometimes it's OK to settle, writes Adam Quan in 2002's deeply magical How to Date a White Woman: A Practical Guide for Asian Men, which attains a dimension of "problematic" previously unimaginable. "You should [try a] lower attractiveness level or at least be with some less attractive woman, any woman, before deciding to go after your most preferred type of white woman. You can learn pick up skills through [an] easy target then trade up," Quan says. If all goes well, you might score a double. "Sometimes seeing the Asian man in the company of another white women of lesser beauty will stir up jealousy in your target woman," Quan writes; consequently, she'll allow you full access to her body and soul. Maybe you'll become her proverbial "white knight with the shining armor," writes Quan. Be smart about the very first step, however. Even if you're only looking for someone to use as bait, Quan cautions for you to stay selective. "Unfortunately some of the best things in life aren't easy, and some of the easiest women to get are not the best ones," he writes. Leave her alone if she's a substance abuser, a chain smoker, a "desperate type," or somebody otherwise considered a "reject of the white men, because they have character defects."

Once you've identified the proper desired female, further your destiny along. "Regardless of what [the] feminist says, women expect you to make the first move," says Quan. To establish interest, "have a long gaze at her, a flirtatious wet eyes glance at her face… Lock in the eyes for a long period… long enough to give her a good impression and memory of that loving eyes contact." Quan recommends you talk to her softly, like you are whispering in her ear. Don't speak at normal pitch; it's too "easy to inadvertently get a speck of saliva on her face." Next, show her your sensuality. She's been wondering this whole time "whether you are skilled in the art of the bedchamber." Touch her lightly about her scarf and jewelry. "The type and suspense of the physical contact will arouse in the white woman the primal urge of sex and the matter of the bedroom," writes Quan, his strange poetry scattering the pages like jewels. "After all that is what it is all about in the end: the search for an acceptable bed partner, who is not a loser."