Short term relationships, casual dating, can get exhausting. Let me share with you Isaac’s story, settled in on an IT career after trying a lot of different jobs and he is 31, from Palm Beach County in southern Florida. After seeing me on Reddit, he decided to come to me for advice because his past dating experiences had all been short-lived. He’d meet a lady, they’d hit it off after a few months, but then it would fizzle out. He eventually realized that there was more to dating than just that. He wanted more. Find out how he overcame obstacles with my assistance in the hopes that it may encourage and uplift you.
**For more clarity & ease of reading, his transcript has been edited**
Talk with Isaac
Ruby: Hi, everyone. Welcome to another inspirational story, and hope that it gives you hope in your own dating journey. So, today, I’m really honored that one of my clients has decided to join me to share his story and his name is Isaac. Hi, Isaac, how are you doing?
Isaac: Hi, Ruby. I’m doing great. How about you?
Ruby: I’m doing well.
Isaac: Thank you for inviting me to do a testimony for you.
Ruby: Of course. Thank you. No, I really loved your story and your journey and I think it is going to help a lot of people. So, we really appreciate it here that you take your time. There’s a lot to talk about. Let’s just jump right in. Tell everyone a little bit about, like, who you are, where you started, and where you are now.
A little Bit Of Isaac
Isaac: My name is Isaac as Ruby mentioned. I’m 31 years old, about to be 32. Pushing the old territory as my girlfriend calls it. I’m located in South Florida in Palm Beach County. Work at IT, but I’ve done plenty of different kinds of jobs throughout my time. I was in the military a couple of years ago, I tried to do pilot. Doing a pilot to be deployed to airlines. But ultimately, my career brought me to it. Once I had the career part settled down, that’s where I want to go into more serious dating.
My dating journey has always been short-term. I’ll meet a girl, hit it off, and then just a couple of months and just be like, “Hey, it’s not going to work out. We haven’t really gone anywhere. So, there are no hard feelings.” At that time, my being more immature side, and my career path being a military, it was one of those, “Oh, you know what? It’s just her. She’s the issue. It is not me.” But as I got older as I got to start putting more effort to save myself career-wise. Likewise, I start to realize that there’s more to dating and I definitely need help. So, that’s where my dating experience was.
The date, is very short-term, nothing. I couldn’t bring someone to meet my family or there was no one to meet my family after three or four months because that was it, and they’ll go, “Oh, another girl, huh? How long it’s going to be?” And then, after a while, it was one of those, I don’t bring it up anymore and I moved out of the household. So, I didn’t have a reason to bring anybody, unless I knew she was the one. That was my struggle. That’s the time to reach out to Ruby.
Ruby: Nice. Give a quick summary of where you are now.
Where Is He Now
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Isaac: Well, from her help, I ended up meeting someone online of all ironic places, dating apps. We end up meeting. She was local. I say local but we’re talking about a 45-minute difference. But we met, I believe now it’s like three and a half, pushing four months. I mentioned earlier that the three to four month was the milestone.
If I could get someone past that, then I’ll be more willing to say, “Hey, I met someone,” and more willing to tell someone, “Hey, I finally got something going on.” We’re at four months. There are no signs of anything where that would tell me that, “Hey, we’re going to end this tomorrow. There’s just no reason we’re–” We have plenty of plans that we’re working together to achieve. The next one right now, we’re looking to move out of Florida and go to the DC area.
Ruby: Nice. Big moves.
Isaac: Big moves, big plans. Everything we’re doing, we’ve definitely an agreement by, the agreement works. We were doing a definite compromise. There are certain things we’re talking about like, “Hey, let’s take your car or I’ll sell my car.” Or, “No, no, let’s sell your car, I’ll take my car.” We’re doing that. “Couple of things.” Things are good. As I told Ruby last time we meet, I’m staying busy, but for a good reason.
Ruby: Right. A lot of things moving forward. The qualities that you’re seeing now in your current girlfriend are things you haven’t seen before in your other relationships, and it’s more promising.
Isaac: Exactly. After a while, I was like, “This is what I’m looking for, but I need help. There’s got to be expert out there.” I guess I found her.
What Did He Worry About At The Beginning
Ruby: I’m so happy for you. Even when you found her and start dating her, I was like, “Oh, my gosh, this is so exciting.” I think you felt it, too. So, I’m happy. Let’s reel back a little bit and talk about the beginning. What did you worry about at the beginning? What did you think would make dating harder for you when you started?
Isaac: The issue wasn’t so much meeting someone, it was I was attracting someone. I believe the reason why I can never make up to three, four, and beyond that was because we were always in this– Let’s just try, I guess, the attraction was never fully there, but no one’s ever truly honest about it. It’s always just, “Let us see if we can make it work,” kind of deal. I think, after doing that fewer times, where there were years where I was like, “You know what? After the last one, I’m done. I want to focus on something.” I was probably far more enjoying my military career, which evidently had a relationship military is already difficult to begin with, but that did play a factor in it.
When I moved and got away from the military and come on my own now, I’m in a city or state that I’ve never lived in. I have no family or friends then. My worry was like, everyone’s talking about, “Oh, you meet this person.” “Oh, this is a friend of a friend of a friend.” I ain’t have that. My only hope right now will be a dating app or putting myself out there to just marking myself the best of my abilities. Both of them were two big majors that I just didn’t know how to do until later talk to Ruby say, “Hey, this is what I’m most likely going to have to do, but I need help.”
Ruby: I don’t know if you remember this, but I remember one of your first texting me when we were about to begin, you’ve been texting me, you’re like, “I’m going to need your support in this. I don’t know what’s happening.” You are like, “I don’t know what to do.” Do you remember that?
Isaac: Exactly. I don’t know if you hear the dog playing with her toys. I don’t know when we’re going to get to that portion. But so, one of the difficulties that what I had was like I said, putting myself out there was, and then I always have a question before the official session, myself and Ruby, one of the most amazing things that she offered at that time was Pocket Ruby. Any question I had, hey, I really want to talk to this girl but she’s at work. I want to know from your perspective, from the woman’s perspective, if you walk up there talking to them, is that something they should look down upon? Would they call 911 to get this creep out of here or throw, that kind of things.
Having a woman’s perspective was one of the most helpful things, I could not use at that time, because I just wanted to see that from that position, especially after where you will have a short relationship go long, go years without having to try another relationship. It’s like, yeah, it throws you off.
Ruby: Right. I love that you mentioned those two major things that would help in this too. Me, being there, but also the female perspective. So, with that, what do you think was the biggest obstacle you overcame?
What Is the Biggest Obstacle He Overcame
Isaac: Kind of piggyback on that was, one, I had to get all of that misconception out of my head. Obviously, Ruby was the biggest one here, because I could google this all or I’d read other books about that written by men. You could try to read on, but you want to talk to Ruby, you want to take her course, you want to just talk to her, figure something out. I get out of on my own head, because I kept fighting against myself, my mental physique, or fighting against myself. I would look at a girl go, “Nah, out of your league. Don’t even bother.” You know what I mean?
Ruby: Yeah.
Isaac: That’s where confidence comes from. You should be looking at someone, I don’t care, because it doesn’t matter, could be the prettiest girl in the world, you should be able to tell yourself, “You know what? I should be able to talk to her.” Actually, the second is that confidence. As I got older and I had these backgrounds working in this, working with that, speaking with certain people, I work in IT. Not the ultimate level, where I’m talking with a computer, but, no, I’m still actually working with people, so I took that experience, I could talk to people because that’s what my job requires, I cannot take this and talk to women now.
And then, talking to Ruby is like, “Yeah, they’re women, but there’s no reason to be scared of them. They’re still a person. So, why not treat them like a person?”
Why not talk to them like you talk to someone if you’re out walking a dog and they have a cute dog, too, and you want to talk to them about their dog? Why not treat them like that?” So, I use that to gain confidence, and stop letting my own mind beat me up.
Ruby: Well, that’s big, especially because you mentioned there are the two biggest things I feel that people struggle with that they don’t notice, which are mindset and confidence. Even at the beginning, I don’t think you wanted to talk to many ladies or approach them. And then, remember, you got out of your head and you just started talking to a bunch of great ladies.
Isaac: Exactly.
Ruby: Even if they didn’t turn to anything romantic, you just make conversations.
From Being An Introvert to Extrovert
Isaac: Exactly. It helps you almost every day. Now, fellas, if you’re listening to this and you’re going, “Well, I’m introvert.” Well, I ask this because I honestly can’t help you there, because I was an introvert growing up. But I am become an extrovert, because of my job and just because of the environment I end up. From my 18 onwards, that’s kind of become an extrovert. Now, I don’t know how would you deal with that. But, yes, that confidence and that talking about. I was talking to– we’ll also have Pocket Ruby before our official training. I remember meeting these two wonderful ladies, they were college graduates of Kansas State University. And the fact that they were at Kansas State where I was stationed there, so I was familiar with this girl and that led to conversations. I remember talking to them.
I was getting ready to leave the area, and I’m staying almost two hours talking to them because of that. There was never a case of– I asked her for advice, “Hey, this kind of situation, what could I–?” We talked for two hours. One gave a hint of a boyfriend, I don’t deny. I was using this opportunity to break down things now like, “What could I have done differently if I were talking to someone else, how would I bring up their single status? Are they looking?” Having the opportunity to ask to have her break down things that you encounter was one most helpful things I could have.
Pocket Ruby
Ruby: That’s awesome. Just so everybody knows, when he mentions Pocket Ruby, that just means that I call myself Pocket Ruby, because you have the option to text me. Basically, whenever you want, whenever you have questions. Obviously, it’s not like you text me at 2:00 AM, I’m going to be awake and answer. But whenever Isaac has questions, he can always text me no matter what it is and I call it Pocket Ruby, because it’s like, “You have me there, in your pocket,” just so everyone knows.
So, you went over the things that helped you with my guidance is more in regards to, I was there for you, I was able to give you some strategies, got you out of your head. Is there anything else that you wanted to share about how specifically, like, my coaching style or my guidance has helped you?
How My Coaching Style Has Helped Him
Isaac: Yeah. I was talking about this before we started the official program. Once we started with the official program, you had the course break down and I’ll tell you coming back with step one to all the after the next step that you’re expecting. Fellas, I’m warning you now, you have homework. There were times when I was too busy or awkward. You got homework to do. This is your life, this is your relationship.
If you’re not willing to put in the effort and do this homework and go out and do things like market yourself, talk to someone, dress better, hit the gym, take better pictures of yourself, and have a brighter smile. If you aren’t willing to do this, I honestly don’t know what did I tell you. This is the stuff that I knew I had to do. Before I even had our official start date, Ruby and I, I told myself, “Hey, I got to do this. I’m going to have to talk maybe a hundred women before I get one and say yes, it’s going to be a date.” I told myself and that’s what happened.
As I was mentioning about the guidance and how she does her classes, it’s very, very useful. Do your homework, and then you’re going to find out things about love and relationships that you may not have thought about, especially when asking about the weakness. Oh, my God. Anyone asks you about your weakness, in your interview, you just start freezing like, “Oh, my God, I don’t know any of my weaknesses.” So, that’s a really good one, because a lot of these teach you about yourself. The more you know about yourself, the more you can market yourself. The more you know about your stuff, you can’t market. Imagine a salesperson who was trying to sell a product they had no idea what it is about. Now you try to sell yourself, but you have no idea about yourself.
Ruby:Yeah, that’s cute. If you don’t know yourself, how are you going to do it?
Isaac: Right. It’s definitely very helpful about that. The topics she is going to ask you about– Ruby always asks me about the love language. That’s a big one too, fellas, that’s something you might want to look into. I know some of you might think, “That’s corny and I don’t care about that.” You may not, but women do. You must know now. She probably will care, so you might want to look into it.
Ruby: Right. Oh, love all of that. The thing about knowing yourself too is also building that confidence, so you know what you also deserve. I don’t think in this relationship that you have, you’re quite confident in it and she’s a great partner. It’s not like you just settle for whatever. I think you’ve built enough of yourself to have that belief that you deserve what you want and not to feel too insecure. So, that’s a big part of learning about yourself.
Isaac: Exactly.
How He Feels Right Now
Ruby: So, speaking of which because I mentioned relationship, tell everybody a little bit about how you’re feeling now? What do you feel for once, like the things that you are enjoying being in a relationship with this person now?
Isaac: Yeah, as Ruby was saying, I’m in a relationship. With her help, I was able to meet someone, ironically do dating app, which I never thought would work.
But how am I feeling right now is be on a nervous side. She’s amazing woman. She’s driven. Well, I say driven, she’s career driven, because she wants to do what she can for to have a good career. That being said, though, there are times where I have seen her laziness and it’s coincided with mine, too. Lazy Sunday mornings and such like that. But she’s got a lot of attractive traits, things that I was looking for when Ruby had me do some of her coaching and training about finding out what you want and so on what she has. So, she’s definitely amazing.
We’re working on to have the next major milestones where we’re actually starting to move in, and we both going to leave Florida. We’re going to go up to the DC area. Now. I’m from the northeast, I’m used to having that city life, but she’s never left Florida her life for God’s sake.
Ruby: Ooh, boy.
Isaac: Yeah, she’s about to see what cold is like, she’s going to see what traffic’s like, she’s going to see what taking public transportation is going to be like and all that stuff. It’s very exciting for us to do this. I did not think I’ll be going back to the northeast, but with her, oh, yeah, I’m willing to go back for her to continue to nurture this relationship and grow and see what happens. That being said, fellas, if you think I don’t have exit plans, you’d be wrong. I always have a backup plan and that’s what my military experience is.
Ruby: Mm-hmm. True,
Isaac: I’m just hoping, I’m like 99% sure I don’t need to use it, but there’s always that 0.001%.
Ruby: Right. The beauty is, we went through a lot of this during our time. So, it’s not like, if anything happens, you wouldn’t know what to do. You do know.
Isaac: Exactly.
Ruby: That’s how you got her in the first place. So, just go back.
Isaac: Exactly.
Ruby: You don’t feel as scared. You know how some people are so attached like, “Oh, my gosh, I need this to work. I need it to work because I don’t know what I’m doing.”
Isaac: Right. It’s exactly what Ruby is saying. Even before I met her and I was talking to other women that was I was attracted to. Yeah, fellas, you think those went well? No. You think I just go up and say, “Oh, well, I’m giving up plan A, B, C, and D.” No, I still have B, C, D all the way up to the end of the letters at that point. Like I mentioned earlier, you had to be determined. You’d think it’s easy, but it’s not. If it was easy, will Ruby be here? No. Will we have this issue? No. So, it’s not easy. Ask yourself what you’re looking and put in the effort.
Ruby: I love it. So, what would you say, especially in the beginning, I know you said I want support, I need the support. Obviously, this is a heavy investment. It was. So, to you, what made that worth it? When you first said, “Yes. Let’s do this,” what in your mind logically told yourself, “This would be good for me?”
Isaac: I end up finding Ruby only from a Reddit post. I don’t know if you guys remember seeing it, do the same thing, too. If you do, then upvote. I got her information on a website from a Reddit post. Of course, I kept that to the side, because at this point where I have not had any successful relationships. I’ve been talking to women, but I was always a coward and just run away as soon as they don’t give me that look I was expecting, the one that my head. Since I didn’t get that I always use excuses, I was like, “That’s her issue, it’s not me,” and so and so forth.
But as I navigate to 2020-2021 into earlier this year, my career path finally improved to the point where finance wasn’t going to be the issue, kind of leading to one, I wanted to take it back on to some of the troubles I had. Boosting my confidence and getting out of my head.
Well, one leading left for my confidence was that, I didn’t want to be– Going back to a while ago, some of the troubles I had so. One of my troubles is that I didn’t really have a career that I’ll be proud of, and two, I know what I was looking for in a relationship. I wanted an attractive woman that had a good career. If you are looking for that, but you yourself don’t have a good career, how can you look for that yourself? Before I could be more sure of or put more effort into say, trying to date, I want to fix myself first. At the end of the day, even if you don’t find someone, sure, you might want to have a career, because how else you’re going to eat? So, that’s what I told myself, “Let me work on my career.”
And then it finally happened about, mid last year into earlier this year, finally landed a good job, I’m making a name for myself, then I thought to myself, “Well, if this part is done, let’s go back into the book of me, and go to the slide where it says dating, and start working on filling this out.” That’s when I contacted Ruby. I was like, “I think I’m ready now. I got the career that would help facilitate the help and I had the time now.” COVID it’s not too effective at this point, and I reached out to Ruby. We had our consultation.
Ruby: I’m happy that you follow through with that. That’s fantastic. There were points in this conversation, where you talked about qualities that would help someone become successful. You’ve obviously done this program. What qualities do you think one needs, a guy needs to be successful in this like you and in this program?
What Qualities Does A guy Need?
Isaac: Qualities, yeah, I’ve mentioned earlier while I was talking to Ruby about the homework. Hey, look, she’s going to ask you to put effort into it. You got to dig down deep, you got to dig deep and match yourself how much you want this. Don’t give up, because that’s usually the easiest part. She says, “No,” and you’re like, “Yeah, whatever. I’m done, I’m going to do something else.” No, don’t give up. Stay on task. Like I say, she’s going to give you some homework. You’re going to do some research, you’re going to probably look at things, topics that you may have never heard of the love language, and lot of other things. Unfortunately, you’re going to have some spreadsheets. So, fellas, that work in the office settings. Yeah, look, there are more spreadsheets. Best of your abilities and answer them.
There was one topic or homework we did where you list out things that were said like, you thought yourself, “She’s beyond me,” or, “She’s above my level.” What was it called, Ruby? It was like you had to break it. Oh, that stopping point, where you’re like pinching yourself or something like that.
There for a reason. It works. And above all, the one I found that was most helpful for me was having Pocket Ruby. Just texting, ask the questions.
Ruby: It’s actually surprising, can you believe that people want to still even if they have me, try to figure it out on their own, but text me, let’s figure it out. That’s why I’m here. So, you don’t have to do that.
Isaac: Don’t give up, use your resources, you got to put some work into it. This is not easy. Everything she’s asking you to do is there for a reason. If someone’s been tested, look at myself. I did it. Heck, some of it, well, I was on the lazy side, so I’m telling you now, fellas, you can be more successful than what I’ve done. If you just follow everything she does to a tee….as well as you can as if you’re trying to get your PhDs right now.
Ruby: Right. Exactly. Love it. And last but not least, to wrap this up. Normally, during this time, people who are watching this are on the fence to decide whether to want to work with me or decide they want this dating support. Is there anything else you want to add to those guys that are still listening right now and on the fence about if they should do it, what would you say to them?
Isaac Stands About Dating Program
Isaac: I’d say, look at your situation. This is definitely an investment in yourself. Not everyone’s going to get out of this three-month program or maybe a one-month program in which what you’re picking and to be like, “Hey, I met someone. We’re dating.” “Oh, hey, we’re exclusive.” Let’s be honest. It’s not going to be this, it’s a low chance that’s going to happen. But, fellas, talk to Ruby. It’s not going to cost you a dime. It costs you, what, I think our first session took about 35 to 40 minutes.
Ruby: Yeah.
Isaac: 30 to 40 minutes, talk to her, tell her what’s your issue, and have her decide to say, “You know what, I can’t help you.” And then from there on, talk more, just asking yourself, “Hey, how much do you want to change your perspective?” Maybe you were married, you’ve been out of the game of dating and you just need help to try to find someone else to fill in that void. I can’t help you with that. But ask her, “Hey, this is what’s happened. What do you think?” And see what she can do.
Ruby: Exactly! I love that, go ahead.
Isaac: I just want to say really talk to her. As I mentioned, I knew about Ruby months ahead, but I pushed it aside because I got to work on myself. And eventually, I did, before I’ve gotten her help, I was trying to go back into the dating scene, it was just– I’ve never been most lost in my life and I work in IT. I rather sit in front of a computer and read how semantics work or how a computer system works and try to go back to dating. Until the day I talked to her and start deciphering some things.
Ruby: Great. Thank you so much. I love that because at the end of the day what you’re saying is, “Hey, one step at a time.” The first step, is just talk, because it’s true, you guys. You can talk to me for free for 30 minutes. I’ll be honest if I can help or not and then we get to decide from there. Then you can take the next step after. So, it’s all about just looking at what’s right in front of you. Great.
With that said, thank you so much, Isaac, for your story, and for everything that you shared. I loved everything that you share and I can tell you’re coming out of this so confidently. And also, really excited about where you’re at with your girlfriend. Thank you so much for sharing. And good luck to you guys and your move. Good luck to her in the cold. If anything, I know you and I will talk here and there, and text. But once again, Thank you!
It’s an honor to witness how an introverted guy like Isaac decided to invest in himself and devote his time to working on himself in order to eventually get into a long-term relationship with someone he can introduce to his family without mocking him about how long it’ll survive. If you’re still on the fence about how to successfully date, schedule a chat with me and we’ll see if we’re a good fit to work together.
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