Jason has gotten into some serious relationships and had several dating experiences, but admits that he has never felt connected to a deeper level with the women he dated.
Aside from the fact that he is a bit of a perfectionist, he also admitted that he relaxed a bit and got more open-minded after we started working together. He explains how my guidance has helped him get higher quality dates and understand women better. Jason’s story will surely inspire you. The transcription was edited for clarity.
About Jason
Jason: I’m 41 years old and located in Toronto. I’m an optometrist, been practicing for quite a few years. I’m yet to get married, and just haven’t really found that person to really connect with, have some dating experience. I’ve gotten into some serious relationships in the past. Some were better than others. I felt lately I just haven’t really been connecting on a deeper level with the women I dated and maybe, that’s why things didn’t work out or maybe I settled, a few things.
Where I’m now with regards to dating, I’m connecting with higher-quality women than I have before. I’ve been online before, but I feel even though that I’m older now, I’m just connecting with women who are really more of a better match for me, higher-quality women. I feel I’ve been able to be more selective with who I’m chatting with. Yeah, it’s a great feeling rather than just chatting with whoever responds.
Ruby: Exactly. It’s such an exciting feeling, and I’ll always remember you would show me the matches that you got. You would say, “Well, she seems high quality, she seems great as well.” It’s great to have that selection, and you’re able to choose instead of just waiting for the women to choose you if that makes sense.
Jason: Yeah, that’s a big difference.
Overcoming his biggest obstacle
Ruby: What was the biggest obstacle that you feel you overcame, or the most helpful knowledge you’ve gained?
Jason: I would say, just getting out of my own head. I have a history of being a bit of a perfectionist, just in my field, and just the way I do things, but also with dating, and I realized, you just got to be more open-minded, and just see where things go. You really helped me with that. Just to open my mind up, adopt a mindset of just being curious, try to learn more about the person you’re trying to get to know better, rather than just focus on your own preconceived thoughts of what you’re looking for.
Takes a little while to get to know people, especially with messaging online. As I got more open-minded, I got to know the women better, and let go of my perfectionist tendencies, and just got more curious about talking with them. I think you gave me great tips on just also how to open conversations especially with younger, high-quality professional women, and I got a lot of responses.
Ruby: I like the balance between– you’re obviously open-minded, but at the same time I’m not telling you to date, everyone, to you, is still being selective with certain ladies, and the qualities that you want, but you’re open-minded to seeing their story, being a little curious about their own journey.
Jason: Yes, the journey. You emphasized the journey with me. That was really key to just opening my mind up, at least just chatting with more people, then the ones that you want to chat with offline, you’d be more selective with that.
How was my guidance has helped him
Ruby: Exactly, awesome. Give us a summary of how my guidance has helped you get the quality ladies you’re speaking of now.
Jason: It was a really good journey. It started from the initial process of just drafting up my dating profile. I’ve done it a few times, and this time, in the process, you gave me some exercises, just to ask about. First of all, you got to know me better through some of the things you asked to get to know me as a person, and what my goals were. Then after that, it was really just making me think about what strengths I have, what things I feel proud of, and also just really guiding me to see what makes me stand out to women.
Then, on top of that, I also just to figure out what qualities I really wanted in a woman. The one that would be best suited for me rather than just being too general, being more specific about things, and putting that in my profile, putting it in my mindset that I’m always looking for.
I thought the assignments really laid out. It was a personalized roadmap for me. It was a good framework for me to just fall back on, as I messaged people online and just wanting to– there are certain things I wanted to know about them, and it was very specific. I felt it was good. It was just very streamlined. I think also your PDFs, some of the work that you gave me to read over, I thought they were really on point. Very specific. I remember like, “Oh,” and it wasn’t like a novel.
Ruby: It was literally like, “Do this, do that. Here’s a short explanation, but here’s what to do.”
The assignments are packed with good nuggets
Jason: Yeah, I was like, “Oh, this is so short,” and then I’m like, “Wow, that was really packed with a lot of good nuggets in there.” I’ve done some personal work before, and then you get these novels. It’s hard to retain that. Yours is just right to the point. I felt a lot of the things you suggested were immediately actionable. It was so easy just for me at least to implement them. They weren’t.
Ruby: Yay, fantastic.
Jason: Yeah.
Ruby: I loved how you brought up the concept of, especially because you were looking for particular or specific qualities, how to bring that up in a conversation, how to pivot conversation sometimes. I know we’ve talked a lot about messaging and conversing. I’m curious what’s the one thing in a conversation that you found most helpful? Whether that be pivoting or confronting what you want, or the things we’ve talked about in conversations, what’s one thing that really helped you out and you didn’t know before?
One thing that really helped him out
Jason: I think it’s just knowing how to ask questions to really elicit– to show them that you’re curious about getting to know them. It’s really just digging deeper. Then, when you ask the right questions in terms of, for the women, the ladies that your messaging, it really does engage them more, rather than just surface-level chat, and that dies down pretty soon. Even though you gave me some crate openers, Ruby, I’ve heard sometimes after the openers, that can die down too and just take care of the conversation.
Ruby: You’re saying it’s about the questions that are asked so that it just doesn’t get stuck in one spot. It’s about asking a lot of questions about her journey, or whatever it is to continue it.
Jason: Yes, asking about the journey, asking about her qualities, and pivoting to ask things you want to know about her. Obviously, you’re not just going to chat about maybe just what she wants to talk about, because you want to get to know her too, in terms of if she’s a good fit for me, or for you. There are certain things you have to know how to pivot smoothly, and just keep the conversation flowing. I think you really helped me with that transition.
Ruby: Thank you so much for sharing that part of it. I feel conversations are really important. There’s a lot that goes to it. I’m glad you’re able to learn different parts of it. Tell us a little bit more about how you’re feeling now?
How he feels right now
Jason: A lot more confident. I thought I was doing okay before, but I feel I’m doing better now. I’m happy with all the quality ladies that I’m chatting up more than before. I just feel I’m getting to really know them better. My goal is to try and build something meaningful with somebody, who’s a good match for me. I think we’ve touched upon it before, having multiple options is a good thing. In the process of chatting with multiple people, or just getting to know people at the same time, you really learn more about yourself and what you really want too. They’re useful people to carry the conversation as you mentioned, you get to know people more.
Ruby: Exactly. Do you feel that you are getting more closer and you’re also more hopeful and finding that kind of partner you are looking for?
Jason: I do. I think that before– there’s actually more matches that I’m getting now than before. It’s hard to keep up. Admittedly, everything you’ve done, really helped me just get more matches, better matches too. I’m just able to be more selective. The fact that I’m being more selective, also helps me feel like, “Yes, I’m really just making a choice that’s really best suited for me eventually,” Even though there are more people, I’m still able to be more selective. I’m really homing in on someone who I think is a good fit for me.
His stand for Asians about getting a dating coach
Ruby: Right. I’m shifting gears a little bit, but usually, many people are too scared to get help on such a vulnerable topic. It can be shameful, and also, it helps people knowing that you are Asian, and I feel a lot of times it’s more painful for Asians. It’s like what used to be therapy, used to be a huge stigma in Asia they don’t accept that. Now, I’ve heard from a lot of different Asians, or even Asian clients saying like, “Oh, it can just be weird, this feels really shameful.” Can you speak to that, and what would you say to them?
Working with a dating coach
Jason: OI feel there’s no shame in working with a coach at all, a dating coach. We seek out help in so many other areas of our life, from working with a personal trainer for fitness, business seminars to help us advance in our work, and also just seeking more education. So, why not do it for dating? I think that, for me, it’s really helped just really focus on what I really wanted and how to attain that.
I think Ruby did a great job of just help guide me. It was a great experience. Ruby also took the time to get to know me, and also find out what I was looking for, and just gave me a good roadmap on how to do it. Working with you just really helped me, open up my mind, change my mindset. As a result, it just really helped me attract and connect with smarter, high-quality ladies.
I really felt that, just along with the way, there were times where I was stuck. Those are the times that I didn’t know what to do. I would message you, and you respond fairly, quickly. I remember I did watch the movie Hitch. The first thing that came to mind is a scene in there. I had to look that up and send that to you because you instantly helped me and I was messaging this very wonderful lady. You helped me get unstuck. She responded, and we continued our conversation. I just felt like, “Wow, what a moment.” It was great.
Ruby: I always remember that. Yeah, you sent me a GIF for Hitch, and the guy was dancing. I was like, “Oh, that’s such a classic scene.” That was good.
Jason: That’s exactly what I felt because I was like, “Well, I didn’t know what to do.” You guided me there. She still responded, and I just got to get to know her better. It was a great moment.
How worthy is the one-on-one program with me
Ruby: Going back to what you said, also I feel like the biggest thing with this program that I feel is helpful is, you got that time with me. People when they get stuck, they’ll start googling, reading a lot of books, the YouTube videos even, but they can’t respond to you in that way with a text. That’s obviously the biggest thing with one-on-one, which actually brings me to the question of, yeah, what are the reasons you notice this investment was worth it when you first said yes?
Jason: Well, just to continue what you were mentioning there, the one-on-one engagement is great, especially when you get stuck. You can only read so much, you can only YouTube so much. A lot of that information is not really personalized and pertaining to at least my situation at that time. When I got stuck, and I didn’t know what to say, I messaged you, and you gave me some really good tips. It just worked and flowed. It helped right at the moment, and it was very personal.
I think, for me, it was really the change of mindset, just to be more open-minded, just to be more curious, focus on a journey more, as you mentioned. The journey of getting to know somebody. It takes a while to really do that. Messaging, it’s a little tough, and that’s the first part that I found a little tougher navigating is the message, and then to try and get to know someone through getting to the phone and the video chat, because during this corona times right now, it’s harder to meet up.
Ruby: Right.
Jason: Yeah, so that was a bit of a challenge too. It was good just to work with you on that and just to change my approach in terms of how I messaged, how I was thinking of messaging, and questions to ask.
Qualities to possess to be successful in this journey
Ruby: Wrapping this up. Usually, the people listening to this are guys that are curious and wondering if they should also work with me, but they also want to be in your spot. They want to receive the results that you’re getting. Obviously, it’s not just me. There’s obviously you, that executes and implements. What qualities do you think one needs to be successful in this and be like you, dating these high-quality ladies?
Jason: Well I admit that your guidance helps me a lot, I think. There are more matches, more quality matches. Being in a position where you have options, it helps. It really does help with confidence, so I do thank you for that.
In terms of what else, I think, it’s important to put the work. There were exercises you sent me, to begin with, and I was like, “Oh, I know this is going to take a while,” but I really took a lot of time doing them. I got to know myself a little better. I also really was focusing on what I was looking for in terms of a partner. While doing that, you just have to trust the process that you set out, basically. It really helped.
His Epiphany Moments
I also had these epiphany moments that I think I mentioned to you. I was like, “Wow, this is what I used to do. This is how I used to message,” which is very direct and not very open and didn’t give the opportunity to be curious and to really get to know the women, in terms of what really made them tick. The questions that you helped me generate the mindset that you helped instill in me. I really broke out on my old habits, and I was just able to really get to know them better, and really have them want to chat with me. I think it really helped. When you do that, you just figure you have a lot of different options, a lot of different conversations going on at a time.
Ultimately, right now, I’m chatting with three women more than others. Now that COVID is wrapping up, I’m pretty excited to meet the three of them. We’ve already talked about that. I’m still messaging some other people. I think it’s just about really finding someone who’s a good match for you. You may have to go through a few people before doing that. I think the mindset that you’ve helped instill in me just really focusing on the journey, getting to know someone really well, and just seeing if they’re a good fit for me, that really was eye-opening for me, I guess.
Jason: I trust the process
Ruby: The fact that you’re able to keep these messages and conversations going throughout COVID so that you can be excited to see them in person, that’s the hardest part. Everyone’s like, “How do you converse with them and keep them interested for so long?” But you just navigate that more. Now, that’s awesome. What I really liked, and also, what makes this successful for you is, thank you for, I guess, in guiding you, but obviously, you are a big part of this.
You are open-minded to dating and to my guidance and that’s what I appreciate about working with you. You’ve always asked why. You’ll have a deeper dive into my guidance, but you’re not like, “Why would I do that?” You didn’t hold much resistance, you just trusted. Even though, let’s say– I remember in the very beginning, remember, you’re like, “Oh, my profile is fine. I think it’s great.” We worked through, and it was like, “Well, if you want these ladies, we were going to– let’s switch it up.”
Jason: Yes.
Ruby: You weren’t arguing with me with that. You’re like, “Okay, I’ll take it. Well, let’s just try.” I really, really appreciate that that quality from you.
Jason: It worked. It worked when you gave the suggestions. It really did. I could tell you really knew what you were talking about. You have a great background in terms of your experience doing all this. The results are there, and I could really feel that you really wanted to help me achieve the results I was looking for. That made a difference.
What would he say to anyone?
Ruby: Oh, that’s awesome. Yes, I care. If anyone doesn’t know, I care about my clients. Even if it is going over time and things like that, I will say until you get your questions answered, because it’s obviously important to you. Okay, to wrap this up, as I said, usually people that are listening to this are wondering if they should work with me, and are on the brink of saying maybe yes or no. For your last concluding message. I guess what would you say to anyone watching this right now that are wondering, “Should I do this?”
Jason: Yeah, if you’re on the fence about working with a dating coach like Ruby, I would ask you, what do you have to lose.
You’re going to be working with someone who really knows what they’re doing, and just knows how to help you. The fact that she does care, and she just gets to know you as a person, really personalizes the experience and you can only benefit from it. I had thought that my dating profile was pretty good.
Ruby helped put it on steroids or it just got a lot better. It was much better after, noticeably better within a week. I think she has amazing suggestions to at least help you figure out what you can do, to improve your– whether it’s your messaging, your profiles, or pictures. These suggestions are proven. She has a very good background in all this. To me, I just trusted the process, and when I did, I got the results.
Ruby: Thank you so much. Jason, for being here, for sharing your story, and your insight, and your growth in all this. It’s been fantastic working with you. You’re amazing to work with. It’s been a lot of fun also during all of it. Thank you so much again. Thank you for being here and thank you, everyone, for listening. Until next time.