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How Do You Ask Out A Girl That’s Much Older Than You Successfully?


Ever notice something odd around date two or three? Namely, that your lady friend’s incredible ass and your three old-fashioneds are no longer helping you avoid that she’s still:

  • Talking about the Kardashians.
  • Bitching about a bridal party snub.
  • Making not-so-veiled references to a shadowy and nameless ex as you begin to question her judgment, not his.

Insert shudder and wince here. Yikes. The age-old question … how do you ask out a girl who you’ll want to see again?

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Unicorns — You don’t have to choose between a great body and a great mind.

Socializing doesn’t have to be like this, seriously. It shouldn’t be like this. A great female body, cutting wit, fun energy, the right amount of crazy and hot, and the sense to tie it all together does in fact come in a singular package. You need to upgrade your demographic. Think bigger and better. Think about how do you ask out a girl successfully with actually enjoying yourself as a key part of success, not just getting a “yes”.

Think . . . older.

You can expect something different when dating an older woman.

Girls who are older than you are interested in the world around them. They have some experience under their belts. They're more likely to know who they are and what they want which means less BS. They're awesomely confident in the streets and between the sheets. We’ve discussed a slew of reasons that dating girls who are older is way better in every way you care about, from sex to independence.

Most importantly they’re way more likely to have outgrown the preoccupations (see also, bridal party snub) and insecurities that make women who are younger intolerable to any sane human. If you can learn how do you ask out a girl older than you successfully, you are going to discover a wild new world of Kardashian-gossip-free awesomeness.

You have what older girls are looking for, and it’s not just a hard body

Women of all ages enjoy men who are physically fit, sure. But there are an infinite number of men who are currently crushing it at Crossfit, and after it’s all said and done and the deadlifting pics are in, it’s not the hardest six-pack abs (or hardest anything else) that wins because they all start to look the same.

How do you ask out a girl who is older than you is by being interesting (which any blowhard can appear to do) and also by being interested . . . that is, expressing interest in women as people. Getting the hang of how do you ask out a girl much older than you successfully every time will vastly improve your dating life, your sex life, your romantic life . . . all of your lives that involve women who aren’t just friends.

The two magic little words

Nope, it’s not “I do.”
Those magic words are, “And you?”

Girls who are older know their value and they are looking for honest engagement and equity. They don't want some guy constantly telling them he likes them and throwing them awkward compliments. They don’t want to be put on a pedestal of attention . . . that’s as lonely and boring as being ignored.

What they do want is to be engaged, which means a mutual exchange. Mutual exchange means that figuring out how you ask out a girl is the beginning, but by no means then end.

She’s perfectly capable of getting ass complete with top-notch brunch in the morning, so you have to be able to offer more than that. If you talk about yourself . . . your job, your sports, your favorite taco joint or greatest travel adventure to date, always wrap it up with, “and you?”

If you make it a habit to use “. . . and you?” as a segue back to the woman across from you when you’ve come to the end of saying whatever you're saying, you’ll send the message that you’re aware that there’s another key player in the conversation and that you’re interested in what she brings to the table. It's probably the single most important thing you can do to avoid being awkward around women.

And she’ll get the message that you know she brings more than just a killer smile. Girls who are older than you already know their value beyond great sex, and you have to show that you know it and appreciate it too.

Learn the difference between assertive and aggressive, and be assertive

Girls who are older than you are confident, and confident assertiveness in men is immensely appealing. Confident women aren’t going to help out men who are flailing or beating around the bush . . . they will watch you struggle briefly and then simply disengage and that will be the end of it. There’s no recovering from that.

How do you ask out a girl successfully every time? Be completely clear about asking her out.

“Got plans this weekend?” is not asking a woman out, it’s asking a girl if she has plans for the weekend. How do you ask out a girl involves actually asking her out.

“Can I take you out for drinks on Saturday?” is asking a woman out.

If you’re not confident in your ability to ask her out, she won’t be either. And get clear on the difference between attentive and overbearing. Girls who are older don’t find smothering flattering, they find it nauseating. Waiting to ask her out is key, especially if you just went out a literal day prior.

They do not want to wake up to a text that says,

“Good morning, Sunshine” or “Good morning, Sexy” after a first date.

This screams desperate and insecure, and suggests that after one date you’ve already escalated to daily and overly familiar contact. They would like to get a text from you 36 hours after your date to the tune of,

“Hey, I’d like to take you out next week. When are you available?”

If she doesn’t want to go out with you again, she’ll tell you she’s busy and will get in contact with you. If she does want to go out again, you’ve just demonstrated sexy assertiveness. Knowing what to say and when to ask her out to avoid rejection is key. When you know this, it’s all win.

Bring your A-game every time

You can meet older women who like younger men in different places. But what matters the most is that you bring your A-game wherever they are. The thing about girls older than you is they have satisfying, busy, independent lives, and they’re not going to make time for subpar anything. Including men. So the secret of how do you ask out a girl older than you successfully is that you better make it worth her time, every time. That means, pay attention.

Offer ideas for dates but be flexible and open to feedback. Don’t be late. Don’t send meaningless texts in between planning and meeting, ala “hey, what’s up?” It’s boring, it’s lame, and it suggests you have so little going on in your life that you are initiating chitchat with someone who is functionally a total stranger . . . it’s overly familiar and smacks of too much free time.

Substance is a huge deal for girls who are older than you, so while you don’t need to bring up global politics in every exchange, skip the bland stuff and use it later on your brother.

How do you you ask out out a woman of depth is the same as keeping a woman of depth? Show extreme respect for this priceless quality.

Girls who are older than you don’t do drama and they won’t tolerate any from you

A refreshing part of dating a girl older than you is that you will find her to be shockingly drama-free and low-maintenance. Don’t take this for granted. The reason her life is drama-free is that she’s experienced enough to be over it and unwilling to have any . . . and that includes yours. And low-maintenance is not the same as no-maintenance. She won't go out with you just because you bothered to send a cheesy pickup line.

So don’t get lazy and remember that girls who are older don’t need anyone and they’re much more aware of that than younger women, so if you drop the ball, they’ll have no reservations about moving on with or without someone else waiting in the wings. Getting the hang of how do you ask out a girl is almost as important as figuring out how to keep her going out with you.


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