Can dating get better if you know yourself better? Absolutely yes! Like my recent successful client Darren, a 31-year-old professional double bass player from Boston, Massachusetts, who struggled with dating due to issues dating back to high school, insecurities, and concerns about being perceived as creepy—the list goes on. Not until the beginning of our private date coaching, where he realized that he possesses negative beliefs that prevented him from finding a girlfriend.
He used to improvise his way through dating and has been trying his luck on his own, he realized that improvising and doing things on his own is ONLY slowing down his dating success. As a private teacher, he sees the value of having someone who is very passionate about helping others, so he decided to take a chance and work with me, and guess what? He received positive results in a matter of months.
He met someone he could only imagine meeting before and couldn’t believe such a person exists. Isn’t it amazing? Continue reading to learn how he overcame his challenges with my one-on-one coaching program.
Just a heads up! The following has been transcribed for clarity.
Conversation With Darren
Ruby: Here I am with another exciting story to share with you all with one of my clients here. His name is Darren. Hi, Darren. How are you?
Darren: Hi, Ruby. I’m doing well.
Ruby: Awesome. I’m really excited about this one and for you guys to hear where he is now in his progress. It was such a joy to work with him. When I kept seeing him grow and where he is now, I am so excited for you all to hear it, and hopefully, it will give you hope in this dating journey. So, with that said, let’s just hop right in. So, Darren, tell everyone a little bit about who you are, where you started, and where you are now.
A little bit about him
Darren: Absolutely. My name is Darren. I am 31 years old, and living in Boston. I’m a professional double bass player. I play classical music and I make a living doing a combination of teaching private lessons, group lessons, and playing for many of the local symphony orchestras in town.
Ruby: Nice, very nice. In a quick summary, because we’re going to dive into this in a bit, what was your dating experience right before me, obviously, and then working with me, but where you are now?
Darren: Before meeting with Ruby, I feel like most of the time I was just improvising my way through dating. I didn’t have a lot of confidence with it, a lot of issues with dating and confidence stemming all the way back to high school. Always worried about being seen as creepy and facing rejection, and certain insecurities would move into a more prestigious kind of college environment.
I was always worried that I didn’t make enough money, I didn’t really fit in with living in Boston. I was always worried that I didn’t have the personality traits that a lot of other guys around here might have an easier time attracting women.
How Far He Went With His Dating Journey
Ruby: Right. Awesome. Okay, so with all of that, where are you now? How are you now with dating?
Darren: Oh, night and day, Ruby. Night and day. I met a wonderful woman. We met on Hinge. We did online dating. I was on it since we started together in December, and I ended with Ruby middle of January, and less than a month later, I met a wonderful person. We share so many similar values, and have used the L word with each other.
We feel really passionately about each other. That’s what’s so good is that I feel like I don’t just have chemistry with this woman, but I feel really compatible with her. I really feel that she also feels equally compatible with me.
So, I feel as much as the training that I’ve had with Ruby is dating coaching, in a way, I also feel like I’ve worked with a relationship coach on the other hand because I was able to learn what I really like in a woman personally and I was able to meet pretty which someone, a person I could only dream about actually. I just can’t believe that this person exists. This is such a great reality now.
What Ruby always does with her clients
Ruby: By the way, guys, I do this with all my clients. I love it when clients share with me their journey and their stories, especially their photos, and you two look so cute together and obviously, very happy together. I think, as you said, the biggest thing that I feel people, I can’t grasp is that girl you dream about, that ultimate compatibility where you actually really enjoy each other and it’s easy and it flows. So, I’m so excited that you found that. I know in the beginning you wondered if that was possible and now here you are.
So, going back here, you did talk about what you were worried about previously and obviously, probably coming into the experience and starting to work with me, all the kinds of obstacles you were facing, what makes dating harder for you? But during our time, what do you think was the biggest obstacle you overcome or the knowledge? What knowledge do you feel you really gained that you realize, “Wow, that’s what changed the course for you?”
What made dating hard for Darren
Darren: Oh, I can definitely talk about this. There were so many different components to your coaching that really helped me out, specifically when we did the Google Sheets at the beginning and really honing in on the different subjects, like, trying to understand myself, my personality, being able to identify what my attractive traits are based on lots of life experiences that I share, and really just starting out the entire coaching in that positive.
I felt like it was a revelation for me in a way to discover more, because we don’t really introspect all the time, and that whole portion at the beginning with the Google Sheets gave me a very generous amount of time to really introspect, take a step back and say to myself, “Okay, so, I have these different negative beliefs that I’ve had in the past. But thinking about it in a different way, I’m able to now meet other people who can appreciate some of my interests and my attractive qualities.”
Darren: That was one thing. Then after that, building the profile, going through that, and learning what that entails,
Ruby was able to share all her knowledge on that. I think that building the profile in the manner in which she guided me really helped to understand how to– And then the results showed for itself.
The moment he built his profile
Once I built the profile, I realized that I was matching with way more women than in the past. I used to match with women a few times a week, but when we built the profile, the way that Ruby had shared with me just some of her knowledge– She’s, of course, worked with eHarmony in the past, although she tends to prefer Hinge and Coffee Meets Bagel, I think, recently.
So, when we were building those profiles, once we finished that, I started actually swiping, I almost couldn’t keep up on certain days. I know Ruby remembers this. I couldn’t keep up on certain days with how many matches I was getting. We didn’t even have to go out and take extremely professional photos or something like that. It was right within my own phone gallery. Of course, I’m sure it varies from client to client, but just the fact that it was more about the actual formatting and stuff like that. Some things like that, I’m sure these apps pay attention to.
The fact that Ruby knows so much about the various apps and what they’re looking for, I think definitely plays a huge role in this.
Back and forth texting
Of course, finally, the biggest one of all, the back-and-forth texting, being able to share screenshots of some of my chats with the women I was communicating with. The most important thing to know is that Ruby is so good. You can share practically any of the discussions that you’ve been having with the women. Sometimes, I’m sure for Ruby, it gets a little bit overwhelming. I sent quite a number of screenshots and questions, but just always know that even with the amount of questions that you send,
Ruby always is pretty good at communicating with her clients and letting me know when she needs extra data to answer it. Once she finally gets around, she always answers everything. When she does, part of the reason why I think that Ruby does things at the pace that she does is she really wants to think through the responses. She doesn’t want to just give you a friend’s response.
This is where I think a big amount of the value comes from with Ruby, she doesn’t just give you a friend’s advice, she’s giving you professional advice. She really sets that relationship up from the very beginning when you first meet her. You particularly get to see just how knowledgeable Ruby is about how much she’s dedicated herself to this all, particularly when you’re sending her those questions and sending her those screenshots.
Ruby: Well, those points, I feel so flattered. For one, you really thought this through and you’ve seen all the details and everything that helps. So, I really appreciate you going through all of that. As I said, I was taken aback. I was like, “Whoa, thank you for saying all that.” The two things I want to add is and you noticed this too, I think, with online dating. Like you said, you were getting matches before, but what was interesting this time is these ladies, not only were they more, but once you started messaging them, they were more compatible with you, and more connected to you. They were good ladies you didn’t go on too many awful dates, right? Some just probably didn’t work out. I remember you saying that ladies are fantastic. Did you hear that?
Darren: Oh, there was just a little break in there. But no, I did hear that.
Ruby: I’m going to pause. I’m probably going to start that section over.
Darren: Sure. Yeah.
Ruby: I don’t know why my phone went off. Okay. One of the things that I really appreciated that you said was about the matches that you were getting, because you were getting matches beforehand. But this time around, you realized the ladies were more connected with you. They were more compatible with you. They’re good people. You went on some dates. I don’t remember too many awful ones unless I’m missing some. And then eventually you found the most compatible for you. So, I think that was great to see and that’s what I always tell clients like, “I’m here to find you quality, not necessarily quantity.” That’s why we build a profile the way we did.
How much time before you respond
But secondly, I love that you mentioned I respond when I do. I don’t think someone has actually talked about that in a video before because I tell everybody I only respond when I’m 100% present. When I’m 100% there, I really read everything and think things through. But also, I don’t know if you noticed this as a client, but it also forces you to practice patience and not needing like, “ What if she’s not answering me, I need her to answer me.” It makes you think, “Okay. It’ll be fine. I asked the question. She will answer, “ Then that way you’re soothing yourself through the process as well. Have you ever felt like that in that way in practicing.
Darren: I admit. There were definitely those moments, for sure.
How does Darren feel right now?
Ruby: Awesome. Now, I know you already talked about where you are and being in this relationship. But can you go into anything else about how you’re feeling right now, especially because you talked about understanding yourself and how you had these negative beliefs before? How are you feeling about yourself now, but also just being in a relationship, how do you feel kind of the feelings in this?
Darren: The biggest thing is that right now, I feel ecstatic. The biggest thing for me is that compared to before Ruby, I feel comparative now, like Ruby said, I’m able to exhibit more patience. So, before I even met my girlfriend, when I was dating when I was still using the apps in between, when I ended with Ruby until now, one of the biggest things is that as we’re messaging people, oftentimes we rush too quickly, I think. We’re always anxious to set that data, we are anxious to escalate things as quickly as possible without realizing that everyone has their own pace. Sometimes, it’s just a matter of appreciating the current conversation that you’re having with one particular match, maybe she doesn’t respond back.
Darren on being understanding
You realize that people have a life, and they’re going to be involved with different things, especially for someone my age. I’m 31 now and so I’m busy with my own things. But we sometimes forget that other people are busy too. They have a professional life, but they have family issues, just like– I think my family is wonderful, but what is a family without issues? Everyone has things that come up, but we forget that people are people.
Yes, sometimes they’re going to like another guy and someone’s going to be more suitable for them, but I’ve realized that people can be really nice and they can be even a very high-quality person, but not everyone’s going to be compatible with you. The person that I happen to be in a relationship with now is compatible and it takes time to meet a person like that.
Ruby: Right. Amazing. Well, I’m really glad that all the feelings right now are just excitement, but also at peace with everything. I remember at the end of our time, you definitely felt so much better about yourself, right?
Darren: Yes definitely!
Improved Relationship with Women
Ruby: Who you are, what you have to offer. So, all those insecurities were there in the beginning, but now you feel really solid in it.
Darren: Yeah. It’s not even that I’m in a relationship now. Even before the relationship, in between the time I ended with Ruby and now, I just felt that my relationship with women in general improved. And so, this part almost makes me a little bit emotional, but I think that some guys who are reading this, they’re going to relate. But sometimes we don’t actually have a positive female role model in our lives. And so, when we go and we have all these bad dating experiences, particularly when I say female role model, someone that’s around our own age, not like our parents or grandparents, but someone that’s around our own age of whom we have a lot of respect for.
Tension with women
I think that for some of us, I feel that some guys out there will relate to this, but many of us have never had a positive relationship with women somewhere our age. Even though Ruby and I were, of course, a professional to client relationship through the coaching and everything. I feel like Ruby was a role model to me, being able to learn what it’s like to have a healthy and positive relationship with a woman for the first time, whether it’s dating, friendship, etc.
Because in the past, I just always used to feel this tension when I’d interact with other women. Because I feel like deep down, I was really frustrated with them. But Ruby helped to really talk about some of these negative beliefs that I formed through all these bad experiences in the past in my dating life and it helped me to focus on new and better qualities in a woman that I’d never considered in the past. So, this helped me to really appreciate the current person that I’m dating. I love the fact that she and I are so open to talking about everything. Sharing everything and feel so much freer in that way than the way I’ve ever experienced dating in the past to have that open communication and Ruby really encourages that.
His Stance On Private Coaching
Ruby: Oh, I love that. I think this is why as well, people have always questioned me and wondered, how can a female dating coach help, right? But I think it is that you’re absolutely right, not many of my clients maybe have that kind of relationship with a woman or even spoken to many ladies potentially. To start off, even with just us, it helps in that. I’m really glad it did and it definitely makes a difference and opens the opportunities up for you to meet your girlfriend now. So, switching gears here, many people are usually too scared to get help on such a vulnerable topic. I mean, it can feel shameful. Can you speak to that and what would you say to them?
Darren: Yeah, as a private teacher myself, when students have trouble learning the instrument rather than struggling with it themselves, they could try to teach themselves, they can try to improvise their way, try to discover how to best play the instrument. But reaching out to a private instructor, someone who’s been in the field for since– Of course, I’ve done my schooling and everything like that.
What Darren thinks about Date Coaching
And yeah, because of my schooling, because of my knowledge, because of the different orchestras I’ve played and stuff like that. I consider myself qualified to speak and to help my students improve in learning the instrument. But for dating, why can’t we have that same kind of mentality? That’s what got me to really consider Ruby as a coach is that, and here I have the opportunity. I have something that I’m struggling with. Overcoming this issue with my dating life, it was a big quality of life thing for me and I decided to be proactive about it.
When I saw that Ruby was a dating coach, that she ran this all remotely, and that she had majored in marriage and family therapy, I think, in the past as well. So, she had the credentials for that. She worked for eHarmony and then she also had all the testimonials from her clients and just watching all her YouTube videos, all of that. When I was even watching the YouTube videos, I can tell that Ruby, it was a very passionate thing for her. She had very insightful knowledge, even through just the YouTube videos alone. But at that point where I decided to go ahead with dating coaching.
The help has been way overdue
Well, I had just switched out. I left a job that was nonmusically related. And so, now I was doing 100% music. I’m doing basically what I wanted to always professionally. The way I wanted to treat myself is to, I said, “You know what? I’m in a new chapter of my life, and this is like, now that everything’s working out for me professionally. I have other areas that are working out for me, why not tackle this Achilles heel that’s been in my life all up until this point?”. Even just signing up with Ruby, that initial step, was such a freeing moment for me to be able to acknowledge and say, “Yes, I’m finally getting help for this. It’s been way overdue.”
Ruby: Yeah. The moment you said yesterday, I love it because, I remember I think that day, or even our first call, you were that excited. You’re like, “I’m finally doing something–“ It’s almost like, I think we’re both people actually really enjoy what we do. I know not everyone can say that about their careers, but when you have that piece of the puzzle just filled in with your career, and then you look and realize, “Oh, there’s still this piece here that’s missing, but what are you going to do?” So, I think especially because we’re coaches and teachers, we recognize that if we want something, sometimes it’s helpful to have someone who knows what they’re doing, so you’re not just flailing around trying to figure it out anymore, you know?
You have to be introspective to become successful
Ruby: So, I love that and it really showed the reasons why you decided to say yes to this investment in the first place, because we all know it’s not a light investment either. You do have to be serious in saying this yes and wanting this to happen for you. So, with that, you’ve obviously been to the program. People obviously probably want to be where you’re at right now, happily in a relationship and feeling good about yourself. What do you think one needs? What do you think a guy needs to be successful like you in doing my program to date successfully?
Darren: I feel that if you want to succeed with Ruby’s program, you have to be introspective, you have to be open to new ways of thinking about things, and you have to be open to occasionally accepting some tough love on occasion because sometimes there are moments where you hold on to certain beliefs for a long time. When Ruby tries to– Wait, but you also have to think about it in this another way too.
Seeing it from the ladies’ perspective
You have to see it from this lady’s perspective, what you’re saying here or it’s one of those things that like, “Hold on, I think you’re overthinking this, and why don’t you just ask her directly?” Things like that. I think it’s in those moments, we can often be like, “Whoa, hold on. How dare you say that about me?” Because it’s these beliefs that we’ve held onto for a long time. It takes sometimes a day.
There’s this one particular call that I remember, and it wasn’t even a call, I had written a whole thing about a particular moment with one of my dates and I had to deal with something I felt insecure about. And Ruby had come back with a four-minute audio message for me, just kind of breaking it, like, “Hold on one second, rein it in.” It’s those moments. Yeah, it’s going to be a little uncomfortable, but don’t worry. The next day you’re going to wake up and you’re going to consider what Ruby has told you, and you’re going to be like, “Yeah, she’s probably right about this. Let me go ahead and try.”
Things you may not want to hear
Even though the advice might not be what you want to hear at that moment, the next day, you’re going to wake up and you’re going to consider what Ruby is saying.
You’re going to know that she has your best interests in mind, and she really wants you to succeed. Not only does she want you to succeed, I feel like she’s really looking for you to have a really healthy relationship, not just succeed and date. Like Ruby always says, “It’s not about winning women.” She always says that. It’s not about going out and feeling like it’s a game and you have to win people. It’s more about expressing who you are, sharing how passionate you are about your interests, really honing in on what–
Ruby always talks about the why like, “Why are you interested in certain things, why do you value the things that you do?” When you share those things with other people, I’ve learned– Some people may not like it, and there are other people who will accept it, and those are the people you’ll end up feeling closer to and you may see more potential in a relationship with. So, no, I’ve learned to really trust her process. Sometimes, there’ll be moments that are uncomfortable. If you have the ability to realize that Ruby wants you in a positive healthy relationship and not just getting out there and picking up people every day. That will really help you to succeed, I think, with this.
Darren appreciates and takes on the tough love
Ruby: Right. Oh, I love that and I love that you saw that in me. I think I tried my best to make it very clear in the beginning that anything that I do, like, the tough love that you shared, because it’s true, I do. But the intent is always to help. And not just help like you said, “Oh, get more women.” It’s not about that. It’s just to help you in general and your overall life and how you feel about life and yourself on a daily basis. I would like to think, even though I can give tough love, I’m not mean about it. I’m never mean. I don’t think I’m ever mean, but I will push you. So, I love that. You obviously know the process. So, you know what it takes.
Darren: Three words. Firm, professional, and respectful.
Ruby: Oh, wow–
Darren: And friendly too. In the moment that counts.
His Advice To Those Who Has Been Struggling With Dating
Ruby: All right, so, in wrapping this up, the last thing I wanted to ask you is normally at this point, especially this call, if anyone is still listening, it’s because they are interested and wondering if they should invest in me and date coaching. So, is there anything you want to say to those who are still iffy or any last words at all for this call?
Darren: If you’re listening and if you’ve been following Ruby, if you’ve been watching her videos, if you’ve been even doing her Facebook group as well, and if you feel like you’ve been really frustrated with your dating experiences up until this point, it’s been consistently frustrating. If you become really jaded about online dating, like even I have, I know that for almost most of us. I’d say, who have engaged in online dating, it can be a really frustrating experience. If you feel that your relationship also with women around our age has been more or less negative and you’d like to see a more positive relationship with women. I highly recommend going ahead with Ruby.
The biggest thing to expect with Ruby
The biggest thing is that, what you can expect if you go ahead with Ruby, as long as you follow her modules, if you take the time to be introspective during those moments, if you send all the different questions, and the chats, the screenshots that you have when you are using the apps. Eventually, if you send those all your related questions, and
Ruby has been more than generous with her knowledge and with the time that she’s spent in the field. I think even for me, initially, of course, it goes without saying, it was definitely a sticker shock at first. I was like, “What? The dating coaching is this much? What?” But no, look, in reality, the type of value that’s behind that, it’s all of Ruby’s time. It’s the amount of time and education and work experiences that all combine together to create this well-oiled machine, I call it.
Darren: It certainly worked for me. I definitely was the type of client that needed this sort of thing. After doing a program like this, if you feel great about yourself, if you feel like you are proactive in trying to take care of an area of your life that you feel like you struggled so much in and you feel so positive after that and you even had success after that, I’m not saying everyone’s going to find someone within a month as I did. But I definitely feel that the stuff that I learned with Ruby and all of those mindset changes through working with her have been so impactful that going forward, I’m really, really grateful to her. That’s all I’ll say. I hope that everyone that’s listening to this and who’s considering Ruby, definitely consider this.
When I first called to ask about Ruby’s program, she took the time to explain the process and answer all my questions. And for me, what really sold me at that moment. I was just like, “I want to be proactive.” A future relationship or even just a massive improvement in your own character is impossible to put a price on.
How Darren felt during the program
Ruby: Yeah. Oh, my gosh, what a way to wrap it up. It’s like you have your own speech, like, preach as if I don’t know any of this.
Darren: Happy to do it, Ruby.
Ruby: No, I really appreciate your time in doing this and everything that you’ve shared. It really walks me through. Actually, your own experience, because I think you tell me these things. But obviously, we don’t talk like this, where I’m really diving in with how you felt during all of it. As Darren said, guys, all it is, is taking that chance to hop on that free introduction call. That’s really it. That doesn’t even necessarily mean you have to take this on or that. I say this to all clients, “I always want to make sure on those calls we’re a good fit.”. That’s really important that we get along, that I know and I feel that I can help you.
Success didn’t come from comfort
But, Darren, you’ve been so great during our program together. You were always eager to learn. You’re always open-minded and stayed open-minded. You listened, even when it was difficult to do so, did a fantastic job of keeping up with the homework and send quite a few screenshots, but trust me, I’d rather be kept in the loop and feel helpless than not have any information at all.
So, thank you so much for sharing everything that you did. Guys, I hope that really inspired you to just take action. If it’s not with me, just take action in your dating and love life. It could be a great change for you. Thank you so much, Darren, for sharing, and for taking the time today. I hope everything works out for you and your girlfriend. Thank you so much again, and I’m sure we’ll keep in touch.
I have had such a great time working with Darren. Like what you have read, his eagerness and determination outs him in his current space. Even though felt uncomfortable at times, he pushed himself to see the results. I always tell my Facebook group community and YouTube viewers to take action because it could lead somewhere. I hope that you got inspired by Darren’s story and decided if you wanted to be exactly in his place.
Want the same results as Darren?
Learn how here