May December Game

The third most frequent email request I receive from readers is advice for how to date younger women. (The second most common email request is of the type “Hey I was a beta with this girl I like. What could I have done better?”. The first is “Meet me this Thursday.”) I’ve written a few times about tactics for picking up younger women and the proper attitude to have with them, but those posts are buried in the archives, so consider this a refresher.

  • Game will obliterate a 5-15 year age gap.

If your game is tight and you’re confident around a girl, you won’t normally have to deal with her objecting to the age gap. Girls simply don’t think logically like that, particularly the younger ones. But occasionally a girl will broach the subject early on, and this will happen particularly if she is not accustomed to dating older men. There are a variety of techniques for handling what I call “teaser objections”. That is, objections which are solicited not to cut off a potential relationship, but to test you for your ability to be comfortable around her, and to thus assuage her concerns being around you.

  • Reframe the age gap

If a girl is interested, expect her to ask about your age. She will ask no matter how old you are. As a Jedi of the female condition, you will have answers ready for any objection. It’s best to turn it around on her so that it is you who is qualifying her. You can see examples of qualification lines in action in this post, which can also be delivered as negs. A common thread to reframing the age gap is to insinuate that the girl isn’t mature/sophisticated/worldly enough for you. You can even throw in a line about how older women seem smarter, and most of the younger women you have dated liked to talk about fluffy TV shows. Remember: Gina tingles are birthed in the defensive crouch position. *Squirt!* Always be on the offense.

Another solid technique is to anticipate her objection. Before she asks your age, set the tone by implying early on that she may not have the self-assurance to be in your company. This should be structured as an early stage qualification routine, which I wrote about here. Most girls will bite on this.

  • Imply preselection by younger women

Sometimes a girl will ask “So do you usually date younger women?” Be careful, as the answer you think is a winner, is not. You will be tempted to tell her that you always date younger women. But she’s just as likely to interpret that as meaning you are an incorrigible skirt chaser of college coeds. It also sounds try-hard. On the other hand, you certainly don’t want to say she’s your first younger woman. That would raise a red flag as well. Your best answer, as is typical in matters of seduction, should be ambiguous and evasive.

“I’ve dated women of many different ages, younger and older. I don’t limit myself based on an arbitrary number. The connection is what’s most important to me.”

She will be left defenseless to the above line.

Older men (where we define “older” as +10 years) will have to be aware that their pool of available younger prospects will be smaller. One, there are fewer single women after a certain age. (Though this is changing. Thank you feminism!) Two, there will be a percentage of women for whom dating older men is impossible to conceive. However, a countervailing force that works in favor of older men is the fact that there is a significant minority of women who *actively* seek to date older men.

The numbers generally break down like this:

40% of young women won’t date older men.
40% of young women *prefer* dating older men.
20% of young women are neutral about dating older men.

As an older man, you will learn to quickly ascertain which of the younger women you approach are most amenable to dating you. One way to look at it is that the older man has an extra filter to apply to his dealings with women that younger men, for the most part, don’t have to worry about.

It is more important than ever that the older man refrain from showing even a hint of neediness or insecurity about the age gap. Younger women will be on extra high alert for signs of clinginess from older men, because after a certain age women will expect you to have your alpha shit together. Younger men can’t afford neediness either, but they have a little more wiggle room than older men.

Whatever you do, don’t make a big deal out of the age gap. Act as if it’s perfectly normal that you and her find each other attractive. Doubt is not only the mind killer; it’s also the wet pussy killer.

  • Feminine girls tend to be into older men; masculine girls tend to prefer younger men

I’ll toss this one to the evo psychs. It’s true; the pretty, soft, feminine women like dating older men, while the skanky, hard-bodied, manjawed sluts and cougars-in-training get their rocks off bed hopping with younger men. There is a certain beautiful symmetry to this emergent natural order — the older men get the exquisite pleasure of sex and love with younger women while the younger men cut their teeth on older women willing to show them the ropes.

  • Broken families are the older seducer’s best friend

The stereotype is true: Girls from broken families love dating older men. Maybe it’s separation anxiety, a latent daddy complex, or a strong desire for a reliable provider instead of a cad. Whatever it is, the daughters of divorce are easier pickings for the older man. If you hear a girl say she hasn’t seen her father in twenty years since mommy kicked him out, you are permitted to do a fist pump when she’s not looking. Again, thank you feminism!

Oh, and this is also true for women raised by much older fathers.

  • Dress young

A lot of raging feminists will complain “Men should learn to act and dress their age!” Nevermind what older, bitter, expired women say. When you dress young, you appeal to younger women. But keep two caveats in mind.

One, be in shape. Youthful clothing only fits properly on slim bodies. I like the Hank Moody look — a pared down artsy style of tight black tee under a fitted hipster jacket, coupled with distressed dark jeans and either super swank shoes or scenester sneakers. I top it off with some mild peacocking, like a ring, leather bracelet, sunglasses, and fedora. But a fat guy would look ridiculous in a similar get-up.

Two, women in their late 20s and 30s will appreciate an older man in a sharp suit. If you are at a charity event where a lot of professional women who normally don’t frequent clubs will be in attendance, you will get more attention attired in a suit and projecting an air of authority and sophistication. As with all things fashion, context is king.

Note that youthful clothing is not necessarily synonymous with “trendy fads”. You can dress youthfully without following the latest youth trends. Try to hit the sweet spot where you look young but you don’t look overtly fashion-forward.

  • Drop the bumpngrind dance club scene

Unless you are an incredible dancer, don’t bother bump and grinding out there on the dance floor with the rest of the drunk rabble rousers. You’ll feel stupid, and you’ll look stupid too. This doesn’t mean your dancing career is over. Older men can shine in structured dance scenes like salsa or tango. In fact, I have witnessed many an older man swoop younger women using tango game alone.

  • Avoid age-restrictive scenes

Don’t take a younger woman out on dates to venues or events that have mostly younger men *or* older men in attendance. At the predominantly young man event, you will stick out like a sore thumb. This will make her self-conscious. At the predominantly older man event, she will stick out like a sore thumb, also making her self-conscious. The last thing you want to do is tempt a younger woman to believe you and her are culturally incompatible. So focus on taking her to mixed-age scenes that you both enjoy. Or skipping the scenes altogether and heading straight for the bedroom.

  • Get up to speed on the latest in music and art

No brainer. Younger women want an emotional connection with you just as much as older women do. The easiest way to connect is through shared hobbies and interests. If she spits out the name of a band she loves, it helps if you know what she’s talking about.

  • Baldness is bad

50% of men by age 50 have noticeable balding. Either shave it all off, or, if it hasn’t progressed too far, do what a lot of women do when their appearance suffers a hit and “get a little work done”. The worst thing is the monk’s ring. Avoid at all costs.

  • Lie

If you know up front that the girl is going to be a short term fling, and she is more than 10-15 years younger than you, it’s sometimes easier to take the path of least resistance and lie. She’ll thank you later after the earth-shattering orgasm. A sneaky way to lie by omission instead of commission is to play the guessing game with her:

GIRL: How old are you?
YOU: Guess.
GIRL: 29?
YOU: Wow, you’re good at this! [Note that you didn’t specify if she guessed correctly.]

Another true stereotype: Foreign girls love dating older men. Bonus: They aren’t fat!

  • Target single moms

In some parts of the country you will find a lot of young single moms. If you know you have no interest in a long term arrangement, you can do very well targeting single moms under the age of 30, because single moms are more desperate to be loved by high value men. Let’s face it, most alpha males will not commit to a single mom, or fall in love with them. Why take on another man’s responsibility, either directly or indirectly? And kids are romance killers, snuffing out spontaneity like a load of wet diapers air-dropped on a brush fire. Plus, there’s that whole distended vagina thing. A buddy of mine once remarked that banging a chick who had had three kids was like riding the log flume wearing a suit made out of eels. However, if you want to experience the thrill of no-strings-attached sex with a much younger woman, you have really good odds with single moms.

  • Grace under pressure

Older men have it in spades. Or are supposed to. Don’t let anything rattle you. Explosions of testosterone-y hurt and insecurity are the domain of younger men.

  • Emphasize a powerful emotional connection

Older men are also supposed to be less awestruck by women’s beauty. One way to communicate this pleasant indifference to her youthful beauty is to discuss her finer qualities, like her surprising intelligence for someone with so little real world experience. Act as if her body is almost invisible to you. Until you get to the bedroom.

  • Be the wise man

Older men are wise men. What was the point of all those years if you haven’t converted them to wisdom? Younger women want to experience your wisdom, but there is a wrong way and a right way to demonstrate your superiority over her. Don’t make a show of being a wise person. Don’t finger wag like a supercilious father. Instead, allow your wisdom to percolate naturally, showing itself only when the moment calls for it. Don’t draw attention to it. She will appreciate it even if she doesn’t say so.

Filed under: Biomechanics is God, Game