Dating Tips for the Average Nice Guy – Interview with Ruby Le

The nice guy is not always sure of himself in every situation. He can get a bit nervous when meeting a girl he likes, and in turn, he might make a lot of mistakes. Mistakes like failing to make eye contact, failing to pay attention to the flirtation cues she is giving, and most tragically, failing to do anything at all.

It is tough to be a “nice guy” and get the girl. This is why today we are talking with an expert who specializes in taking the average nice guy, and turning him into the good gentleman that (almost) every woman wants. The bad boy may be more successful with women compared to the nice guy, but the good gentleman will always lead the most successful relationships and end up the happiest in the long run.

How can a guy make that transformation? Well, let’s address that question by first saying that the nice guy is most everything women want – they just don’t know it yet. That may be some tough news to read, but the good news is that you’re at the brink of overcoming this issue just by the fact that you’ve found yourself at this article, and to the advice of Ruby Le, a.k.a. the “Good Gentleman” dating coach.

Ruby, help us out:

Urbasm: Should a shy man seek to overcome his shyness… or learn methods to live with it?

Ruby Le: Shyness is like a habit that can be changed. Shyness isn’t actually a bad quality unless it hinders you from talking to your colleagues, your family member or, or most importantly — a girl you’re interested in. Think of shyness in the workplace — you’ve most likely had to learn techniques to overcome it so it doesn’t get in the way of you at a job interview. 

It’s okay if you’re introverted — that’s a part of your personality. Shyness, however, especially extreme shyness, needs to be reduced if you want to make any level of connection. Because how can someone be interested in you if you can’t talk about yourself? 

(if you want to talk about the root/method to overcome) the best starting place to overcome shyness is recognizing the root it. Shyness to the point of paralysis stems from fear. Fear of judgment, rejection, or the unknown. Once you tackle that fear, you can start overcoming shyness.  

Urbasm: What are the biggest mistakes nice/shy men make that cause them to fail to attract women?

Ruby Le: Shy men don’t do anything — that’s the biggest mistake. If you don’t make the move, how can anything happen? If you don’t try, you fail automatically — because nothing can happen. But, if you at least try, you have the potential of success. And if you don’t get her, you learn from it. Shy guys fear rejection or judgment, but what they don’t realize is the consistent avoidance leads to zero progress (and even regression). If the shy guy can at least try to put himself out there, tell the girl he’s interested right when he feels it (instead of months down the road), he’ll get his answer sooner, move forward, and he can take the feedback for future experience. 

Urbasm: Are there any actual “techniques” that help to get the girl, or is it more of a change in attitude (or something else)?

Ruby Le: It’s a little bit of one, but mainly another. There are best “techniques” in dating strategies such as how to talk to a woman in public or crafting the right kind of online profile. 

But, mainly, before any “techniques” are provided, how a man perceives his situation, how he approaches dating is EVERYTHING. If you don’t have that, dating success is extremely slim to none. You can learn all the techniques, but your own mind will sabotage any chance you have.

Urbasm: Okay, let’s get down to a very key point for men. What is the core thing that most women want?

Ruby Le: CONFIDENCE — yes, I’m sure everyone says that one word. But, it’s very true. What is confidence though? It’s being your most authentic self, accepting yourself for who you are and not seeking approval from others. Women want someone who is sure of themselves and sure of what they want.

Urbasm: Why do the good guys sometimes get passed up for the bad ones?

Ruby Le: There are three types — the nice guy, the good guy, and the bad boy. 

The nice guy cares TOO much about the girl to the point he caters to her hoping SOMETHING is reciprocated, bending over backward for her with his time, energy, and emotions. He’s too afraid to challenge her because he doesn’t want to cause awkwardness. He’s not as confident in himself, he’s only confident he can cater to someone else and his value is based on that. 

The bad boy is unapologetically himself and will not bend for anyone. He knows what he wants, when he wants it, and isn’t afraid to go after it. Women will lean towards the bad boy because most women will fall for the seemingly confident self — it shows security and stability (because HE’S secure and stable with himself) However, the bad boy is cocky, not confident — inconsiderate, extremely selfish, and only cares for his own needs. He values himself and his accomplishments. 

The good guy is the guy all (quality) women want to be with and the guy men work up to be. The good guy knows who he is, is proud of it, and not afraid to vocalize his thoughts/opinions. He’s, also, considerate, thoughtful, and respectful. He’s open to learning, always wanting to be the best version of himself. He does things because he wants to, but doesn’t expect anything from another. He’s happy with doing what feels right to him. 

Nice guy – “How can I change for you?” Bad boy — “I will never change” Good guy — “How do I want to change to be the partner I want to be?” 

Urbasm: Where are the best places to meet women for the nice/shy guy?

Ruby Le: Because it takes time for the shy guy to warm up, online dating would be the best method. It gives him time to think with messaging and eases that anxiety. However, if online dating isn’t done right — it can kill the self-esteem further, so make sure you know which platforms to download, how to write a profile, and the shy guy especially needs to be comfortable in talking about himself (most importantly, his strengths) 

Urbasm: What is the worst thing that shy guys do that kills the libido in women?

Ruby Le: Most women appreciate a man who takes the lead, makes decisions and knows what he wants. This includes [while] in bed. What kills libido in a second is waiting for a man to make the move, you can sense the hesitancy, basically when a woman has to say “you tell ME what you want! Make a decision.” 

Urbasm: What should any guy focus on for a conversation during a first date? 

Ruby Le: One Word: CONNECTION. How do you two connect? Focus the conversation on finding where you connect on lifestyle, values, and beliefs. Move past talking about interest, more about what makes you, you

First Date Speed Round

Dress Up or Casual?

Ruby Le: Dressy casual — I will not pick an extreme here (laughs). Because showing up with a tux or a bow tie is simply too much, but showing up in flip flops and a tank shows you put zero effort in this date and could care less. Dress according to activity. Dress to impress, consider an outfit you can wear anywhere and won’t be denied entrance or feel out of place, but without needing to make any of you feel stiff.

Good go-to: Polo, jeans, and nice shoes. 

Dinner or Dancing?

Ruby Le: Dancing — it’s fun and it’s easier to connect with someone through an activity. Dinners can feel too much of an interrogation 

Treat or go Dutch?

Ruby Le: Treat — Rule, if YOU asked her out, you treat. Even if you have an awful time (if you did, just cut the date short and leave it at that). It was your choice to ask her to take time out of her day to be with you, so hopefully, you can trust yourself in that choice. 

Kiss or a Hug?

Ruby Le: Hug — Unless you have over-the-top-extreme chemistry where it’s no brainer you kiss, always go for the hug. You don’t want to step over boundaries, and quite honestly — the anticipation & excitement will grow for the next date if she did want a kiss :) 

Talk about Ex’s or Finances?

Ruby Le: Exes — both potentially touchy subjects. It’s about how you talk about it and how far into the details you go. But, if you had to choose one, exes. It shows where you’ve been, how it’s helped you become who you are, and what you’ve learned. Finances are personal information and would feel like an invasion of privacy if it’s any other question beyond “what do you do for work?” 

Urbasm: Is there anything that still remains a mystery to you as far as the complex nature of a relationship between a man and a woman?

Ruby Le: Honestly, there will always be part of the mystery. Because, though we can say “most” men like this or “most” women enjoy this, that’s the thing….it’s “most” and not “all” — because we all are different human beings. I think it’s important to grasp reality of the population as a whole, however, it’s more important to accept we can’t know it all about someone else (not even when you’re in a relationship!) all we can do is know ourselves and look within, solve the mysteries of us that we can change. 

Urbasm: And our final question is… What are the three things that every man needs to know to be more successful with women?

Ruby Le: Know yourself, your why, and your how. You have to know yourself (the good, the bad, the ugly, all of it), know why you want to be in a relationship in the first place (it helps you continue forward through the tough times), and HOW you’ll take action to actually be successful.

Thank you so much Ruby Le for spending some time with us. And if you would like more help on this topic, visit her website at

Read More on this Topic

The Modern Art of Being a Gentleman – Interview with Dr. Dain Heer
Ken Page on Sex, Hooking Up, and Why Deeper Dating is Better
The Truth About Seduction, Dating, and The Pickup Artist
How to Seduce Women – The Wing Girl Dishes On What Most Dating Coaches Get Wrong
April Masini on Sex, Picking Up Wome, and Why Men Fail

About Dr. Eric J. Leech

Eric has written for over a decade. Then one day he created, a site for every guy.

About Dr. Eric J. Leech

Eric has written for over a decade. Then one day he created, a site for every guy.