The Gentleman’s Guide on How to Ask a Woman Out, and Succeed

How to ask a woman out

Asking a woman out can be one of the most intimidating things a man has to deal with, right up there with job interviews and a first meeting with potential in-laws. For ordinary men, the mere thought of even knowing how to start talking to a girl may fill them with apprehension. There are, of course, basic etiquette that all men must follow, such as dressing to impress and being courteous. But for a gentleman, there are certain key points to follow when he learns how to ask a woman out. Below are but a few samplers of many potential tips that comes with knowing how to ask a girl out on a date.

Be Confident, But Not Cocky

Many men who have experience dating may already know that confidence is everything. A woman loves a man who exhumes confidence. However, for ordinary men, their self-proclaimed confidence may border on the line of cockiness. As the old adage goes: “Women loves bad boys.” Which might hold true in certain cases, but more often, women are attracted not to the rebellious nature of these so-called “bad boys”, but to the level of confidence they display that empowers them to boldly communicate what they want and go after what they want. In other words, the appeal lies in their proactive nature.

How to ask a woman out

When a gentleman ask a woman out, he needs to show absolute confidence in his own qualities as a man. He needs not verbalize his own strengths or point out the weakness of another man, because those are signs of a small-minded man with hidden insecurities. His very actions, demeanor, and tone of voice should send a clear message that he has enough confidence in himself to be asking a woman out.

When you verbally broadcast your qualifications as a man, it comes off as being cocky and may even turn away some women who don’t agree with your self-evaluation. But as a gentleman, a woman should be able to sense that you are confident in your qualities without you having to brag about it, whether or not she agrees with your qualities is her business that is not even up for debate, because you’ve never promoted yourself. Simply put: Do show what kind of man you are, don’t tell.

Be Earnest, But Not Desperate

How to ask a woman out

Many people remember the iconic scene from the 1989 film “Say Anything” where John Cusack stood outside the bedroom window of his love interest Diane Court with a boombox. Since then, this very scene has been considered, and at times even emulated, by many love-sick men who desperately wanted to know how to ask a girl out on a date. This might work if you were in a Hollywood movie and you were John Cusack. But for the average men, this seemingly romantic gesture might appear overly aggressive, even intrusive, especially if you are learning how to ask a girl on a first date.

When a gentleman is learning how, or even when to ask a girl out on a date, it is important to be earnest, but not desperate. It is very easy to blur the line between the two, so here are two case scenarios: When you ask a girl out and she refuses you at first, your sense of self-worth takes a hit and you begin to describe how great of a guy you are and how much she would be missing out. This might be true in your own eyes, but in her eyes, this approach reeks of desperation: Desperation for attention, and desperation for recognition.

How to ask a woman out

A true gentleman, when asking out a woman, will not allow himself to sink to that level. When he is rejected by a woman, instead of lamenting on the qualities she will miss out on, he will shift the focus to the qualities he admires about her that he will miss out on. You need to show her, not tell her, that you are an earnest gentleman looking to building a meaningful connection with her because you hold certain traits of hers in high value, and not just another playboy searching desperately for his next one-night fling. She will be more likely to regard a man who notices and appreciates her qualities. A true gentleman doesn’t beg for attention, he earns admiration.

Don't Get Ahead of Yourself

When a man learns how to start talking to a girl, there is often a dread and fear of being rejected. For certain men who have absolute confidence in themselves, the opposite might be true- When they ask a girl out on a date, they EXPECT the answer to be yes. Both of these are common mistakes that an ordinary man might make, but a gentleman must not ensnare himself in this trap. Don’t underestimate yourself and admit defeat beforehand, and don’t overestimate yourself and assume you’ve already got the girl.

How to ask a woman out

Even if you felt like you’ve “played all your cards right” when asking a woman out, so to speak, she might not sense the same chemistry and spark as you do. Don’t jump to your own conclusions about whether or not she should accept your proposal, let a woman make up her own mind and be prepared to accept any response, positive or negative, with courtesy and class.

If a woman insists that you are not compatible, don’t take it personally. There may be external factors that are unrelated to you that prevents her from reciprocating your interest. Maybe she is not looking to date anybody at the moment. Or perhaps she simply might not be interested in you as a potential romantic partner. Regardless of the reason, maintain your composure. Don’t be pushy just because her response didn’t meet your expectations, respect her boundary and decision-making skills.

How to ask a woman out

It might seem like you’re giving up, but this type of response shows her what kind of man you are: one who is strong and confident enough that a single rejection will not affect his moods and behavior. Besides, one rejection does not spell a death sentence, it may just be that you will have the opportunity to cross this bridge again, it will be best not to burn it with your previous actions.

Don't Over-Analyze Everything

When learning how to ask a girl out on a date, a key step is actually working up to the point of asking. A major mistake that many men tend to make at this stage is looking too hard at the little signs that might hint at a higher or lower chance of success. There are many tips all over the internet that teaches men how to interpret a woman’s level of interest based on her body language, tone of voice, and verbal response. Some of these tips may even have some scientific credence to them. But a cold, hard fact remains: you just never know.

How to ask a woman out

First of all, there are a variety of factors that play into how each woman respond to someone she may have an interest in, such as age, upbringing, ethnicity, religion, and previous dating history. Conversely, not all positive signs point to a romantic interest. When you over-analyze the little things, you risk jumping to conclusion and miss the opportunity to know her on your own terms.

A gentleman need not rely on the science of “decoding” a woman through external references. Rather than generalizing the woman he wants to ask out with a handbook, he embraces the privilege of discovering her unique style and preference by building a meaningful connection with her, and in the process grants her the opportunity to discover him in her own way. There are, of course, certain major signs that should not be ignored, but a true gentleman with sufficient self-confidence ought to trust his own judgement.

How to ask a woman out

“How do you ask a woman out?” is probably a question that every straight men have had at some point. Some people turn to older, more experienced peers for sage advice, while others scour the internet for articles such as this. Whatever advice you choose to follow when considering how to ask a woman out, always remember that there is no magic formula for instant success.

Every advice you’ve ever heard or read, including this one, should be taken with a grain of salt. Your ability to win her over is a two-way street: You need to charm, and she needs to be charmed. Have confidence in your own virtues as a gentleman, and perhaps the woman you want to ask out will begin to value them as well. Just remember to always stay classy.


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