Wondering how you can have more success and fun in your dating life? Today we are joined by men’s dating coach Harry Wilmington for a conversation around topics such as texting do’s and don’ts, how to move from a dating app to a date, and the importance of taking the lead as a man. This conversation reminds us of the importance of having confidence in dating and why leaving a little bit of anticipation and mystery is the key to building attraction. 

Celeste and Harry even dive into why it is important to keep your space clean and organized – because how you take care of yourself will reflect on how you take care of your date! This episode is a must-listen for anyone who is looking to improve their dating game.

In this week’s episode, we discuss:

[01:24] About Harry Wilmington

[02:47] How Harry started helping introverted men

[07:34] Texting etiquette, advice, and mistakes

[13:33] The importance of building anticipation & leaving a bit of mystery

[19:45] Men are on a faster timeline than women

[24:53] Why it’s important to ask the woman you are talking to on a dating app on a date

[27:07] Women want men to lead and plan dates

[32:38] The impact of confidence in dating

[34:28] Dating should be fun

[38:20] Bringing awareness to your patterns 

[45:52] Women do not want the pressure to be perfect

[48:36] The importance of keeping your place clean and organized

[54:27] Embrace the differences between men and women – learning how to communicate

[56:42] Recognizing and understanding our triggers

[1:01:16] Harry’s favorite date

About Harry Wilmington

Harry Wilmington is a seasoned dating coach with two decades of experience empowering men to navigate the complexities of relationships. Through his unwavering dedication, he has become a trusted mentor in the realm of modern romance. With a profound understanding of the intricacies of human connection, Harry specializes in demystifying the female psyche, equipping men with invaluable insights into the dynamics of dating.

Harry is committed to fostering meaningful connections and empowering his clients to forge fulfilling relationships. His profound impact extends beyond mere dating advice, as he instills confidence, self-assurance, and a deeper understanding of interpersonal dynamics. Through his guidance, countless men have transformed their romantic lives, embarking on journeys of self-discovery and love with newfound clarity and purpose. Harry Wilmington stands as a beacon of hope and guidance, illuminating the path to romantic fulfillment for introverted men everywhere.

How Harry started helping introverted men

When Harry was nine years old his father died and as a result of this, he did not have any male guidance growing up. He was not sure how to go about dating and being an introvert, it made it even more difficult. He was not going out and getting practice or trying to talk to women. When he went to college, he realized that women were attracted to him but once he started making moves, they would lose interest. Even though he was being a nice guy, he was losing out to the men who were not nice to women.

In his senior year of college, he had a close female friendship and she started to show signs of interest. At this point, he was studying the ins and outs of attraction, how to talk to women, and what signs to look for to show that they are interested in you. He thought that he was going to win her over but after three years of friendship, they could not make things happen in dating. This led Harry into a spiral of depression.

He ended up watching the movie “Breaking All The Rules” where the lead character wrote a book on how to break up with someone. Harry thought “Wouldn’t that be funny if someone wrote a book on how not to get women instead of getting them?” This led him to write his first book, ”No Girls For You.” This is a step-by-step book for men on how to lose women. In the book, he talks about how you lose women by doing all of the things that you think you are supposed to do like over-complimenting, over-calling, getting gifts, and not talking about sex. This led him to start writing blogs and once he had a handle on getting women, he realized that he could help other men and he became a coach.

Texting etiquette, advice, and mistakes

One of the top questions that Harry receives from men involves texting issues. Whether they have not heard back from a woman they are texting or that they are not getting the responses that they are looking for – on some level, texting has been a detriment to many men. Many of us grew up without texting and people still managed to get together. Men take things very literally and when they hear that “women bond through communication,” they think that the more they communicate with her, the more of a chance they have for them to like them. 

In Harry’s personal experience, over-texting a woman does not work. He also has a lot of female friends and he has heard them complain about the ways that men text them. Celeste shares that if a man is blowing up her phone, it screams that he is needy. This is the fastest way to repel a woman because they do not want to take care of someone needy. Harry tries to teach men that they need to treat texting as a weapon in the sense that they need to know when to use it and what the purpose is. 

Another big mistake that Harry sees men make is that they think they can build rapport by texting. Asking her questions works on an online dating site if you are meeting for the first time but once you get past that step, you do not need to over-communicate by texting. Harry shares that less is more when texting a woman and the only thing he uses text for is asking for dates. He wants to get this in-person time where he can have his words understood without misinterpretation.He has also found that it is better to have a woman miss him in between dates. He did an A & B split test where:

A. He dated a girl and texted her right after the date 

B. Waited longer after the date to text. 

He found that if he waited longer, he was more likely to get another date. 

The importance of building anticipation & leaving a bit of mystery

Harry shares that women like a bit of mystery. He does not ask them for another date when their date is ending, he waits a few days. He always makes sure to show the woman he is with a good time. He tells the men he coaches to take her on a dinner date, go on a walk on the beach, listen to her, and make sure she knows you are attracted to her but do not overdo it. At the end of the date he recommends giving her a hug and saying “Get home safe”. He found that when he did not text them for a few days after this, her interest level started to rise. It is important to build this anticipation. 

For example, Harry worked with a team of women and one of them said that they were going to a party with a man on Friday night. On Monday morning, she said they had a great time but she did not hear from him yet. Harry thought that she was going to lose interest in him but the opposite happened. She kept thinking and talking about him. Harry reminds us that we can be patient in our texting and we will not lose the woman’s interest that fast, it may even keep growing. Celeste shares that high-value women want to know that you have hobbies and a life for yourself. Please do not overshare on a first date, remember to keep that mystery!

Men are on a faster timeline than women

Harry shares that men have a bad habit of falling for a woman fast. He reminds his clients that it takes women an average of two to three months to solidify their feelings. This gives them time to see if a man is consistent in who he says he is. A mistake that men make is that they want to move fast. He reminds men that you do not have to give away what you are feeling so early on. Take your time because both sexes need to asses each other. If a woman wants to know your feelings about her, she will ask you. Men analyze things a lot faster and they know if someone is a match for them much quicker than women.

Celeste sees both ends of the spectrum. She also sees men waiting around wasting women’s time. Harry reminds his clients that women have a three-month program. By two and a half to three months, do not be shocked if she comes to you wanting a relationship. If you are not feeling something after a month, make sure to break things off with her. It is not fair to string her along just because you want a hook-up or to be with someone. Men have to take responsibility and be fair to women too. 

Why it’s important to ask the woman you are talking to on a dating app on a date

Celeste shares that many of her clients end up texting within dating apps or texting on their phones but they do not actually meet. Harry has a program called “Smart Digital Dating” which helps men set up their dating apps and message women to get dates. Harry said that a woman once told her that it was her first date off of a dating app because no other man asked her before. Sometimes men have a habit of texting on the app because they do not want to mess things up or scare someone off. They also think that you have to build rapport before a woman says yes to a date which leads them to spend 4 weeks talking with them through text. 

Harry teaches his clients that the goal of online dating is to have enough of a conversation to meet in person to build a real connection. Online dating apps are just a simulator and the way that you win is meeting her in real life. 

Women want men to lead and plan dates

Harry shares that women do not need expensive and extravagant dates. He has found that even places like comedy shows or going out for pizza are great. Women want men to take action and plan something for them. They do not want to hear “What do you want to do?”. As a man, come up with one or two places at a few different times during the week and give her a chance to choose. Men also want women who trust them and all of this starts with the first date. 

Celeste shares that men also need to pay attention to a woman’s dating profile to get a sense of what she would like. You can lean on the conversations you have had and if you have a list of places where you would normally go, choose the most aligned from those. A date with an activity is always a great idea, especially if you are an introvert! 

The impact of confidence in dating

Harry shares that back in the day when he first started dating, he was nervous and anxious. He would bring this energy on dates and it would affect both of them. As he started to gain confidence in himself, he found that he would be less and less nervous. 

If a woman is trying to find a man who is going to lead, he needs to come in with confidence. Of the two sexes, it is more important for the man to be confident. It will have a bigger impact on the date. When Harry studied communication and how attraction works, it made him a more confident dater, no matter how his date felt. Women love confidence and eye contact! 

Dating should be fun

Celeste reminds us that dating should be fun. The first few dates you should be having fun together, see if you vibe, and see if the chemistry is there. One of the main things Harry has to teach his clients is that it is called the honeymoon phase for a reason. You have the right to just make it fun. For men, even if they meet a girl as their fun and lively self, they may end up getting very serious quickly once they like them. Women are looking for a man who puts in effort to make things fun for her. 

Bringing awareness to your patterns 

We all have to bring awareness to our patterns or we are going to keep bringing the same ones into different relationships. Harry has a free webinar called “3 Nice Guy Dating Patterns That Turn Women Off and What to Do Instead”, where you can become aware of these dating patterns. In Harry’s life, he noticed that he went on a couple of dates with a woman and she would be gone. He had to start looking at what he was doing and make changes. 

It is a hard thing to acknowledge that we are not already perfect. We have to admit to ourselves that we have things to work on and ways to be better for our next partner. If a guy does this work on himself, he does not have to wait to jump into another relationship or start dating again after a breakup. Harry reminds us that if we are not making the right efforts, then every time we try to do something it is not going to work out. We need to be willing to do the work to get what we want. 

Harry shares that logically, men hear that women want them as their authentic selves. Once they think about that, they do not want to change their patterns because they feel as if they are being inauthentic. Celeste shares that we need to elevate ourselves to the highest level. We need to work on ourselves physically, spiritually, and emotionally. Have the goals and momentum, this says a lot because women love when men own their shit. 

Women do not want the pressure to be perfect

Harry reminds us that women do not want the pressure to be perfect. They do not want the pressure that all of your happiness and self-worth rely on them. The reason why women go after “bad boys” is because they already know that she has a naughty and bad side to her. No one wants to be idolized or feel as if they are on a pedestal. No one is perfect and once we can accept that about each other we can understand what we like or do not like. 

The importance of keeping your place clean and organized

Harry has a program called “Introvert Dating Success Academy”, where he goes through the ins and outs of how to meet, greet, attract, date, land, and keep women. In one of the sections, he talks about how to do a first date successfully. One of the things he says is to always assume that something could go down. She may invite herself over to your place so you always want to assume this opportunity may arise so be prepared. It is so important to have your place clean because if a woman sees that you are not taking care of your place, she will think that it carries over to her. She will not care how she views you or what you could do for her later, this stuff matters. 

Even if you have roommates, keep your room clean. Celeste shares that if you are a mess a woman does not want to be your housemaid. She is making sure that you are dateable. One of Celeste’s friends went out with a man who had really nice teeth, dressed well, and then he pulled up in his Mercedes with his car a mess. She just completely shut down and was turned off. Make sure to keep all of your spaces clean. Harry also shares that men need to be aware of the small things. The things that men think are small are big for women such as clean fingernails. 

Embrace the differences between men and women – learning how to communicate

Harry shares that there will always be things that the other sex does that you have no idea why they do it. We need to adjust accordingly. Men have to keep an open mind about what works instead of being stuck in their ways trying to figure out why things are not working. There is no reason to get mad at the way each of us is built. Men cannot want feminine women and then be mad that they are that way. You can either learn to speak another’s language or be frustrated. Learning how to communicate with each other and keeping an open mind is key!

Recognizing and understanding our triggers

Harry shares that if he is dating someone and they hurt his feelings, his first thought is that it was not intentional. They may have been unaware that this was a trigger for you so instead of accusing them of not caring, you can tell them how it made you feel. This allows for more open conversations and then the other person knows not to joke or make comments about that anymore. 

Many people go into arguments assuming that the other person is trying to hurt them. They feel like they have to defend themselves which causes an entire blow-up over something that was a misunderstanding. Everyone has triggers from childhood and past relationships – we need to recognize and own them. Celeste reminds us to go into conversations nonconfrontational and lead with our hearts.

Harry’s favorite date

Harry says that when a woman puts forth effort, that makes it a great date. As the man, he is already planning everything, and when a woman can say “No, I got this”, he is very appreciative of it!

Connect with Harry:

“3 Nice Guy Dating Patterns” Webinar





Introvert Dating Success with Harry Wilmington

May 20, 2024