If chasing a girl means losing a girl, then the opposite is also true: if you can get a girl to chase you, she’s yours. And if you’re an older guy, the most effective way to get a younger woman to chase you is through strategic conversation. It’s not about what you say, but how you guide the interaction. The key lies in asking the right questions. When you know what to ask, she’ll do most of the talking, taking the pressure off you…

When you ask the right questions, you also start shifting the power dynamic. Most guys ask questions to keep the conversation going, which is like playing checkers but you need to learn how to play chess, where every question is a strategic move to get her to chase you.

Before we get to the questions, let’s quickly go over why specific questions—what I call “chase-trigger questions”—get a woman (especially a younger woman) trying to win you over. Typically, men chase women, which almost always fails. To get a woman to chase you, she needs a reason to chase. Today, we’ll cover three types of questions that trigger a woman to chase for three different reasons.

First, we have “QUESTIONS THAT SET A STANDARD.” These questions dangle a carrot, baiting her to chase. Next, we’ll cover “QUESTIONS THAT VALIDATE.” These tap into the “golden mirror” principle, making her crave your approval. Finally, we’ll go over “QUESTIONS THAT DISPLAY AUTHORITY.” These allow you to subtly showcase your mastery and knowledge, which establishes your value.

We’ll use these three triggers—carrots, validation, and value—to turn the tables and get her to chase. But keep in mind: it’s a slow burn, not an immediate switch. The goal is to introduce a chase trigger and then build on it with follow-up questions that fan the flames. Now that we’ve laid the groundwork, let’s dive into the questions!

1. QUESTIONS THAT SET A STANDARD

If you want a woman to chase you, you must give her something to chase, which means you must set a standard. And to set a standard, you must know your standards. As an older guy, this shouldn’t be a difficult question to answer. You should know what you’re looking for in a woman; chances are, you probably do. However, what you probably don’t do—or at least don’t do effectively—is communicate those standards to the women you’re interacting with.

Most guys don’t set standards. This often means the woman sets the standard, making him chase her, which leads to her losing interest. Even if you’re one of the few guys comfortable expressing his standards to a woman, chances are you’re going about in a heavy-handed way. Simply listing your standards and expectations almost always comes as a buzzkill. While it’s good you’re setting a standard, you’re doing it at the cost of disrupting the vibe.

A much better way to communicate your standards is to embed them in a question. So, rather than saying, “I like intelligent women,” you might ask her, “So, what’s the last good book you read?” Or, if you like worldly or adventurous women, you could ask the craziest place she’s ever been or the last country stamped on her passport. By setting a standard this way, you do a few essential things:

First, you’re showing her that you have standards—but in a subtle way. You’d only ask the last good book she read because it matters to you, which communicates what you’re looking for and gives her something to chase. Even if it has been years since she read a good book, if she tries to answer the question, it sets the frame that she’s trying to live up to your standards, which gets her in the habit of chasing you.

Now, if a woman DOESN’T answer the question. For example, if she says something like, “I don’t read,” this isn’t the worst thing. It opens the door for some flirtatious banter. One way to handle it would be to playfully challenge her by saying something like, “You don’t read? What?! Are you serious?!” which puts her on the spot a bit and creates some tension. Most women will push back, saying something like, “The last book I read was in high school or college.” 

One way to respond would be, “Ah, that makes sense. You stopped reading because no one showed you the good books…” This gives her an out, allowing her to agree and take your side while maintaining her pride. Even better, you position yourself as someone who knows what the “good books” are. Once again, this is a great way to set a chase frame because most women will be curious and ask, “Alright, so what are these good books I should be reading?” By saying that, even if she’s still a bit skeptical, she’s confirming that you have knowledge that she wants to know. In other words, you have a carrot you can dangle to get her to chase you.

Think of it like an itch that she’s asking you to scratch. At first, it may just be a slight itch, but the more you dance around without scratching it, the more it intensifies. Whenever you’re getting to know a woman, and you can tell she’s curious about something you said, use it as a chase trigger. So, if a woman asked about books she should be reading, you might respond, “Ah, I’ll tell you once I get to know you a little better,” or, “Sure, I’ll give you a reading list in a second, but first, I want to ask you about” dot, dot, dot, and change the subject. You want to dangle the carrot just out of reach. Don’t say, “no,” but you do want to say, “not yet.” If you understand how to dangle a carrot just out of reach, you know the secret to getting a woman to chase you.

2. QUESTIONS THAT VALIDATE

Communicating your interest in a woman is essential since no one chases someone they have no chance with. However, you need to communicate the right kind of interest… and in the right way. If all you do is shower a woman with compliments and kiss her ass, you’re going to make yourself look desperate and pathetic. And you’re most certainly going to kill whatever attraction or respect she might have had for you.

A better way to communicate interest is by validating and recognizing her for something she had to work for. This is much different from a flattering compliment, which praises her for something she was born with, like her looks. When you validate her, you speak to her on a deeper, more intimate level. And almost all women find validation more gratifying and attractive than a meaningless compliment she’s probably already heard a thousand times.

To do validation the right way, pay close attention when she’s speaking and she’ll tell you exactly the way she wants to be validated. This is so critical. The secret to standing out amongst all the other guys vying for a woman’s attention is recognizing her for how she wants to be seen. You may have heard this technique called the “Golden Mirror” because you’re reflecting on a woman’s idealized image of herself.

One of this would be if a guy met a young, busty blonde girl who maybe looks like a stripper. As you can probably imagine, at first glance, a girl like this would seem like your typical sexy bombshell, now imagine this. Imagine this guy starts talking to her and he quickly realizes that sexy bombshell is NOT how this woman wants to be seen. By listening closely to what she’s saying, and based on how she chooses her words, the guy gets the sense that she wants to be seen as intellectual and cultured—not simply sexy. 

Now, if you find yourself in a situation like this, you don’t want to simply say, “You seem smart” because, while not a terrible idea, it doesn’t contribute to the vibe. And it could come across as supplicating. Instead, you want validate her in a more indirect, but powerful, way by asking her a question like asking her for a book recommendation. To return to our example, you might pull out your phone and said, “Hey, so I just finished the book I was reading, and since you seem like someone who reads a lot and has good taste, give me a good book to order from Amazon.” I guarantee if you ask a strategic question like this, your stock will go way up in a woman’s eyes.

Notice how asking a pointed question doesn’t just TELL a woman you think she’s smart or has good taste; asking the questions SHOWS her. And it’s as simple as embedding validation into a question. Most guys never think to do this. If you tell a woman you like something about her, and you really mean what you say, TREAT her like someone who HAS that admirable quality. So, in our example, the guy didn’t just compliment her intelligence; he started treating her like an intelligent person whose opinion he respected.

Understanding this can separate you from every other guy she’s talking to. If I had to pick five dating skills, mastering the “Golden Mirror” would definitely be on that list. So, it’s a skill you should work to master. First and foremost, that means becoming an attentive listener. Listen closely when a woman’s speaking, almost like a detective. Ask yourself: what does she seem to value the most? What quality seems most important to her?

To take this a step further, consider what she might do with her time if she didn’t have to work. Or, see if you can remember a unique word, expression, or phrase she might have used, and then consider what that might say about her personality or how she’s trying to portray herself.

Once you’ve zeroed in on a characteristic, quality, or skill that you think is a core component of her identity, the next step is figuring out how to SHOW her that you see her this way rather than simply TELLING her. As I mentioned earlier, asking her something often is an easy way to do that. Whether asking for a recommendation, advice, or just her opinion, validating her through a question is a very effective way to communicate attractively with women.

3. QUESTIONS THAT DISPLAY AUTHORITY

Anytime you’re an authority or have mastered something—especially if it’s something a woman is interested in—it’s an attraction trigger. Even having a basic understanding can be attractive, but you must establish your knowledge in an understated way that doesn’t seem like you’re showing off or bragging. To do this, once again, we can use a well-placed question.

Let’s examine this concept with an example. Imagine a guy meets a girl at bar or in a coffee shop. They’re just getting to know each other, so the guy asks what she does for work. She says she works as an editor for a fashion magazine. It just happens the guy also works as an editor. Consider what most guys would do in this situation. They’d probably blurt out, “Oh wow, I’m an editor, too!” But that’s not the best approach…

Imagine if, instead, the guy responded in a way that showed he has some insider knowledge of the industry. So, maybe the guy might ask, “Oh, are you an actual editor? Or just an editorial assistant?” People who work in publishing know that you often start out working as an assistant before you become a full-fledged editor. By asking the question, the guy demonstrates he understands her world, and that he has insider knowledge.   

Likewise, he could ask her, “Oh! An editor, huh? So your name’s on the masthead—that’s impressive.” Again, a masthead the section of a magazine that lists the editorial staff, which most people never look at, but people who work in publishing notice. Since it’s considered an accomplishment to be on the masthead, a statement like this not only displays insider knowledge, but it’s also a form of attractive validation. You’re complimenting her in a way that displays you also understand her world; a very nice and very attractive 1-2 combination!

I hope you’re starting to see how questions with insider knowledge and jargon can establish you as an authority. Another benefit of this technique is it keeps from coming off as overeager. In our example, if the guy simply blurted, “Oh! I’m an editor, too!” there’s a good chance that would kill the vibe of the conversation.

Whenever you tell a woman, “Oh I do that, too!” the conversation often becomes predictable and stale since we can imagine what would probably come next, right? It’ll probably lead to questions like, “So what magazine do you work for? How do you like working there? Do you know so-and-so?”

In other words, the conversation will sound more like a job interview than two people flirting. That’s why you always want to show a woman your authority or insider status rather than tell her.

So: there you have it! Three types of questions that trigger a woman to start chasing you! By dangling a carrot, validating her golden mirror, and subtly displaying your value, you tap into powerful triggers that leave women wanting more.

Now it’s up to you to start implementing what you learned the next time you talk to a beautiful woman—especially if there’s a significant age gap. And when you do, please share your experiences in the comment section. It’s a great way to get feedback as well as it really helps motivate other guys who are also looking to improve their interactions with women.