Jeannine-Kaiser Wolfe

In this episode of Just Call Jenna, Jenna sits down with renowned matchmaker and dating coach Jeannine-Kaiser Wolfe to explore what it really takes to find lasting love. Rather than focusing on dating strategies alone, the conversation dives into the idea that healthy relationships begin with self-awareness, self-love, and doing the inner work first. Together, they unpack limiting beliefs, common dating myths, the difference between dating intentionally versus casually, and why emotional compatibility often matters more than many people realize.

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Jeannine also shares the relationship patterns she consistently sees in her clients, explains how becoming your authentic self naturally makes you more attractive to the right partner, and offers practical encouragement for anyone who feels discouraged about finding love. With relatable stories, expert insights, and even a few humorous dating experiences, this episode is a thoughtful reminder that the journey to finding your soulmate starts with becoming the person you'd want to date yourself.

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Welcome back. Today I've got my friend Janine with me, Janine Kaiser Wolf. We met and she's the author of Soulmate Quest, a book, but she's a matchmaker, a dating coach, known as America's Dating Coach, and the Love Doctor, which I love. I am not in the place to date, but we became friends and here we are. Yeah. So Janine, thanks for being here. Thanks for having me. Had no idea when we met that we'd be here. I know, seriously.

Well, it's it's been a journey for me. I like that. So uh you know, I'd love to be able to share some of those that journey with people and that's how I became actually an expert in the dating and the relationship world is always out there doing the work myself. Uh I am not ready to do the work, but when I am I know exactly who to call. Love that. So one of the things that I think we've come very full circle on is that we talk a lot about brand and where we're supposed to be and sticking with there. And your book talks about that too.

How do you see a brand? In my brand, my brand is actually holistic. My brand is working with people not only on finding the right person, but being ready for that. A lot of people just start in the middle. And so I love my brand is holistic in my approach to finding that right person for somebody. Okay, I like that. I think about my brand a lot as like peace.

And if I have a hard time making a decision, "Is this bringing me or the people around me peace?" Then if not, it's just gotta go. But I love the idea of brand. Like I joke and say I "Stay in my lane, my whole lane, and nothing but my lane." Yeah. I think there's too many choices out there and it's easy to get over one.

Absolutely. We talked about that just the other day. Yeah, how important it is to stay in your lane, right? Yeah. Uh and and give people the value that that you offer. Right. So and how would you encourage someone who's gonna be dating to figure out what value they might have to offer someone or what value they're looking for? Yeah, I think that you have to be able to look at yourself first and what what is what is it that you're looking for and you want to be able to look at am I ready for that relationship? And so a lot of people start in the middle without starting with themselves. "And that's a very important part of our dating coaching uh platform and our organization is helping people figure out what they're all about and uh and then we can steer them in the right direction." Uh the person that she bo she be with be with. I get it. Be with.

And what do you think is a common thing where people don't realize what their brand is? Is that something you run into a lot where trying to coach people to see like what their brand is and how they're presenting themselves. Is that a part of it? It can be. But a lot of it I what I see is a lot of people are beating themselves up emotionally. We have something that we call the itty bitty shitty committee. Yeah I love that. Don't you love that? I do love that. And giving you negative feedback about yourself and it's really smart because it happens really fast, right? So I think there's a lot I have to work with people to get them in the right frame of mind. So they're able to look and find and attract the right partner into their experience.

I love that because I think I remind myself all the time,

"Nobody is meaner to me than me." 

I know, isn't it crazy? If anybody talked to me the way the voice in my head talks to me, I would cut them out of my life. It wouldn't matter if they're a family member, a friend, or just a acquaintance. Oh yeah. If people were saying the things that my head says to me. Yeah, absolutely. I uh and I see that all the time. And it it happens so fast though too, those little things that your itty bitty shitty can be saying to you is so quick that a lot of times we're not not identifying that we're actually doing that.

I think I read Mel Robin's book about the high five, right? Giving yourself a high five every morning. This was a while ago, but it was the same ideas. We're all so mean to ourselves. "How about just being your biggest fan." Absolutely. And I do that in my own line now. Yes. But I can think back in my life of just constantly judging myself. Beating myself up, telling myself I wasn't good enough. I don't really do that now, but I can see that that damages your brand. It's like putting tarnish on your shiny gold shield.

Absolutely the truth. And a lot of people are they're looking for a partner that's a great partner and there's things about themselves that they need to address before they're actually going to find that right partner. So I think that that's an important element of what we do in our coaching is helping people get to that place. That they feel good about choosing a partner, being that partner, and they're ready for that relationship. To me that sounds like like compatibility. Are you compatible with what you're choosing? Yeah, absolutely. Very, very true.

What does that compatibility look like to you? Is it emotional, physical, like what is the thing that makes relationships last? Yeah, you know, what was interesting is the emotional compatibility, right? And that is your level of maturity to be in a relationship. You know, I think every relationship that hits a a roadblock is because one or both are not emotionally mature enough to actually handle the conflict, right? Um every relationship's great when you're in the honeymoon stage of that relationship. Sure. You know, it's it's fabulous. We're all having a good time.

"And as soon as you reach that negotiating phase of the relationship, that's when you can tell whether this person has got the maturity to actually move this relationship forward." 

And that's an important element. I like that. The most important.

I remember in I mean, I'm not a therapist, but I've done a lot of therapy and healing after what I've been through.

But had a therapist that when healing with something that I've carried around from a divorce for a long time was "Age doesn't equal maturity." And that's sticks with me to this day.

Yeah. Partly because it was about the other person, but I also realized I wasn't as mature as I'd like to think I was. Yeah. I am now, but I wasn't that. I know. You know, we we all find new ways, right? And, you know, your your personal journey journey has led you onto a lot of you know, growth in general. Oh yeah. I don't even recognize myself. I sometimes think of what I call Gen A one point oh. Yeah. And I'm like, wait, I can um remember, but I feel so disconnected from that, almost like she's gone and this is me now.

Yeah, you and I talked about that because we both had near to death experiences. And those near to death experiences cause us to have a quantum leap into a newer version of ourself. And and I have to say that that led me into the person I am today, that coach I am today, the matchmaker than I am today. Had that not happened, I wouldn't be where I am today. So you know life throws us interesting things. "They they gave gave us lemons and we created lemonade, right?" Yeah. Life isn't like that, especially with love. It takes um it takes a while to get what you want. Yeah.

I think everything has like its gestation and growth cycle and we are in a society or a culture where we don't want things to cultivate the way they should. Yeah. And I can realize if I think about my relationship patterns, that was more what it was. I was now now now it has to happen quick. Oh I met somebody I think we're a match on paper or this fits what I'm looking for right now. Let's grow up and get married and do these things. Like my first husband, it was, you know, have the kids. I was looking for a partner to get married and have kids. Yeah. That ended. I ended up with a second husband that I just wanted somebody to worship the ground I walked on, and that turned into a stalker. Yeah. "So I think I wasn't giving things times to develop and be what they were." Yeah. And so that was my pattern. I don't think that's my pattern now, but yeah. My pattern now is to put that over on the side.

Well there's two sides to that. One is, you know, you want it now, right? Yeah. And then the sure too. Yeah. And then there are the people that they don't intentionally uh drive the relationship. There's six months into the relationship and no one's talking about where the relationship is going, right? So there's no plan on that. I've seen so many women six month them themselves to age 40 with no child, no family. Uh because they keep doing that, right? It's important to have both sides of it, right? You have to be able to drive the relationship as well. Let it develop, but have a plan. Are you guys looking for the same thing? Are you looking for marriage? Are you looking to have kids? Are you what do you want out of that relationship? Which is super important as a matchmaker that I get people that are on the same page.

And what would you advise someone? Let's say you're coaching a client, they meet someone, they get in a relationship six months in. They start going different ways. Is that something they come to you for? Or do you advise them to go find like couples therapy or something? Well, we actually do coaching. Okay. You know, my job as a matchmaker is not only to have you meet that great person, but to help guide you into that relationship and to avoid some of the pitfalls that people make but they make mistakes. Everybody makes mistakes when you're in a... No Janine, I'm perfect. No, I know you are but... But but you know, part of what I do is to coach people through the challenges that they've had in the past. So that they don't recreate those in their next relationship.

And what happens if somebody like doesn't know their deal breaker and it happens and they're like, I don't know if I should stay or I should go. Yeah. You know what's interesting is your relationship list is a living, breathing document, right? So and things can change, right? But if something shows up and it wasn't on your deal killer list, you you still have the right to walk away from a relationship that's not going to serve you for the long haul. I mean these things show up. This relationships are where we learn a lot about ourselves. Yeah. And uh it can either heal us or sometimes not.

I love the list theory in Steve Harvey's book, he talks about writing a list and writing 300 things that you dream of. And he even talks about like as you go through it, you'll get to like the first hundred, and it's not that big deal, but somewhere around 150, you're gonna hit like a writer's block and you push through and like the idea of getting to those three hundred. In your book you talk about the relationship list. A lot of books that are talking about that, that's one of the big things that people say is making a list, like writing it down. Somehow it's forcing you to be aware of it. But when I get there, I'll write a relationship list. I love that. And how often do you find that trying to coach people that they're not as self-aware as they'd like to believe they are or that they can't see their patterns? How does that work?

You know what's interesting, we all have blind sides, even myself, you know. I've had, you know, work with coaches as well and found blind sides to myself. And I think it's important to, you know, always try to strive for self-awareness, but everybody's... You know, we talk about new souls, old souls, yeah kind of thing. People are almost born with a level of wisdom that and then we acquire more wisdom. Yeah, I agree. And you know, and so but people sometimes think that they're more aware than they're not. A big part of my job is for them to help them find that, right? It's their journey. I'm there to coach them through that. And it's kind of fun to be able to do that. I have a lot of people go, "Oh my gosh, I didn't see that." Um, and those are my fun moments.

I love those moments. I like even with the clients that I've worked with, I like that there's a difference between that old adage of I can lead the horse to water but I can't make it drink. Yeah. It's very difficult when you cross and come across somebody that's just unwilling to do the work.

"I can help you with all the tools and resources, but you gotta do the work." 

You know, when you get really close to the truth, right? A lot of people get very resistant. It is. It's blowing up their world, right? They're how they think and what they believe about themselves. And change is hard for people. Yeah, absolutely.

I try to think of things like varying degrees. For me, it helps to see a lot of things almost like a teeter-totter or a seesaw. Like things move, and my job is to just not fall off the end of a seesaw. My work as a coach is to help somebody examine some of these and what did you learn from it? What where did you go after the situation? Where are you going now because of the situation? These are good questions to ask somebody. Yeah, I get that. Yeah.

What do you think is probably the hardest thing you have to face with clients and helping them to be the right partner? Everybody's so different. Yeah. It's really hard to like put your finger on just like one thing because everybody is just a unique individual, right? Sure. With unique systems. So I just think not getting discouraged.

You know, a lot of people get very discouraged in the process. "You have to kiss a few frogs in order for you to get your prince or your princess, right?" 

And um people... Had enough frogs in my area. I've had my share of toads as well. Sure. We have lots of fun, interesting stories regarding some of those toads. But yeah. Yeah. But I think it, you know, just everybody has to find their own way. And my job is just to help them get there.

Yeah. I think of like when I'm working with the people I'm helping. Um, I always think about like, how do I guide you? How do I help you find the lake? If you don't want to drink, I can't help you. Yeah. Like my mom always said you can guide the horse to water but you can't make it drink. Exactly. What do you think is one of the hardest things for people nowadays to make connections? Cause I feel like with digital, we're all getting further and further away from that human connection. So how do you help people bring that back? Yeah. Actually connect.

You know, that's a great question. Because social media and apps really harmed people out there that are looking for the right person. Everything got uh it's it was like almost a wall between the people. And there weren't a lot of places to go to actually meet the right person, especially when you're going midlife, back out there dating after a divorce or being widowed, etc. It's like where do you go to meet quality individuals, a lot of those organizations went away. And so we're seeing a rebuild of that. "I'm actually helping out there rebuild some of these organizations so that people can actually go and meet people." It's not like you walk into a party and you're 20 years old and everybody in the room is single. You walk... Not anymore, not anymore, right? And so it's like where can you have your best opportunities? And that's kind of where my organization is going, is helping to rebuild some of these organizations so that we get some healthy people out there that can be in the same room.

And uh like my seminars are a great place to meet people. Yeah. You know, you have people that are doing the work. And uh and you have a room of, you know, 60 to 70 people that are doing the work. And these are some opportunities. I always see too, do what you love. Right. Yeah. You know, like I love pickleball. There's a lot of single people that are playing pickleball. And there's even a singles app for pickleball. I really... a friend of mine just told me her girlfriend just developed this app, so I've got to go check that out.

But you know, "Do what you love and then things seem to follow because your energy is aligned with the thing your passions, what you love." I get it.

So what do you think is the thing that holds people back the most? From becoming that partner or making that leap into finding a partner or wanting to find a partner. I mean most people are like, yeah, I'm lonely, I'm gonna go find somebody. But what do you think holds people back the most from sort of doing the work to get to be that person or be ready for that if that may you know to make that leap of faith? Yeah. "I think it's really simple. We don't teach stuff." We go to school, we learn all this stuff, but we don't learn things about relationships and about, you know, how to have good relationships, etc. We don't learn this. No one's teaching it. Except for me. I'm teaching. Well, yeah, I get it.

I felt the same about banking as I was shocked at because nobody told people about finances. I was shocked at how many business owners I knew that didn't understand that they had to balance their checkbook. Exactly. Didn't understand that they need to follow... Yeah, I was shocked at how many people I knew that were successful that knew nothing about money. So I get what you're saying. Absolutely. So we think that we have this as innate you know, built-in opportunity to just go out and meet people, but it you have to work on that. "It is like an exercise you have to exercise it." Yeah. Not everybody can be the extrovert I am. Exactly. You and I are both extroverts. Yeah. That's great. And I see some people at our events, it's so painful for them to be there.

But the more you do it, the better you get at it. Yeah. "Just like practicing anything." Right. Right? And uh tell people go practice, right? Okay. I like that theory.

What do you think is the funniest dating story you've ever heard? Well I can't tell my client's story, but I can tell you my funniest dating story. So my funniest dating story, it was when I was on Movin 99.7 radio, Baltazar and Maria in the morning. Baltazar, he and I are still friends. He was a prankster, okay? So I had this guy that I was connecting with, and we were gonna meet for lunch. He kept pushing it back during the day. So we went from lunch to three o'clock, switched locations, and that's okay. But he shows up and he's eaten at a hof brau, so why did I not have lunch with him at the hof brau, right? And he's bringing me this rice pudding. And he wants me to try a bite of this rice pudding. And I'm not gonna take a bite out of rice pudding that somebody is putting in front of me. And uh so then he starts telling me his life story and it's like a bad country song, right? Okay. Everything is uh the things that happened with his kids is part... it just like, oh trauma after trauma after trauma. And he says to me, "And I'll move anywhere that you want because I don't have any money."

Wow. Here I am across this table from this guy. I'm going... Was your jaw on the floor? I'm thinking Baltazar is pranking me and I'm looking around to see if there's cameras because it's so crazy, right? Then he pulls out this antique case with wedding bands in it. And he used to be a jeweler and he wants me to pick out my wedding set. Oh. Anyway, I went to the restroom, paid the waitress, and I snuck out the back door. And it's like... What those crazy moments. Is that not a crazy date? That is crazy.

I think I can remember one that I went on maybe 10 years ago, I'm gonna say. So I meet this guy who I'm set up with by a friend, like you guys are a great match, and he's one of those successful, up-and-coming, like 40 under 40 type guys. And we go on this date and he starts talking all about his family, his brothers, and how to impress his mom. And I'm thinking, this is awkward. Why are we talking about your mom? Yeah. And so then he goes on and on about, you know, just success and sort of keeping up with the Jones type stuff to the point it's like turning me out. And then he starts being rude to the wait staff. Oh my god. Like the waiter, the waitress, the manager did one of those coming over, "Is everybody having a good time?" "Actually I'd like to complain about this..." And I'm thinking, okay. So I'm really at this point irritated and just want to get the hell out of there.

And then he makes a comment about going to the movies and it being dark and fooling around in the movies. I just opened my wallet, dropped my cash on the table and said, "I'm done," and went and got an Uber. Oh yeah. But I was... I just couldn't believe like what world are you living in that you think this behavior is okay. And if the... how... what... what did you think you were gonna impress me with? Yeah, isn't it crazy? I mean people think this is okay. Right. Yeah. You know? But you know, there are a lot of good people. And I've gone on some good dates. So I'm sure you have too. Everything's varying degrees. Yeah, varying degrees. But uh yeah. But I bet we could swap stories for... Oh yeah. Yeah I've heard some doozies.

Well I dated a hundred men in a single year, first dates, right? Yeah I think you say that in the book. Trying to figure out what I wanted in life and it was great. First dates just coffee, lunch, dinner, whatever. Just a simple date. So like the practice, like just get comfortable with it until... Yeah, and I was able to ask some really good questions and I didn't have anything to lose by asking some bold questions. "So it was actually a very good experience for me." Okay. Yeah. I like that theory.

Yeah. But you never know when a person is gonna walk in your life. I had the men that I met were not online, right? They were they walked into my life. Yeah. My late husband was at school at the coffee machine. That's how we met, at the coffee machine. And then my husband, Ken, I met him at a pizza parlor. I know. I read that in your book. Like it's my favorite pizza place too, by the way. I love that place. And we've been going there... Pinky since I was five years old. Yeah. I think I've been going there since it was at the old location before they moved. Exactly. That's where I was sort of. Yeah. Yeah. So when you started talking about that story in the book, like I could mentally visualize all of it because I knew exactly what it looked like, what it smelled like, everything about it.

Exactly. Exactly. And it's so funny because we both have been going to that same pizza parlor for years, right? And they all knew me and all knew him, but we never saw each other until that day. "And I think that neither one of us were ready until that time." And I think a lot of times the person walks into your life when you're ready. And it happens a lot. Yeah. We talked about, you know, the attraction magnet too.

When you're in a good place emotionally, you're able to draw in better things, the things that you want.

Yeah. I think that's definitely a law of attraction. The idea that like attracts like. Yeah exactly. "You have to be an energetic match to that." Absolutely. And if you've ended a relationship, it's important to take the time to detox from that relationship. You know, uncouple from that relationship. And then you'll be ready to actually jump in and find the right partner. And not be a dating story we talk about on the podcast. Exactly, exactly.

Maybe one of those. So yeah. I think as humans we naturally want growth. Many of us are afraid of it, but I think we naturally want to grow and expand. Yeah. I know I do. Yeah, I agree. You know, and growth in relationships is important too. And it's important when a couple is growing that they try to grow together, right? Because you could end up in completely different spaces, right? It's nice when you have some commonality that actually helps you bond and grow together. I get that, yeah. I think communication is key. Very much.

I think I told you recently that I had seen something where there were these relationships and there was this couple that was married and instead of talking about like the till death do us part, they just every year on their anniversary, they went to Puerto Vallarta and they would commit to the next year. "I'm gonna stay with you no matter what, and we'll sort of renegotiate that or reapproach it next year." And I was like, no, that's a commitment I might be able to make. I can live with a year. Yeah. I think that that's I think that's a great thing to do in any relationship is re-examine your relationship. And then you don't end up having the things that you stack on top of each other, right? And don't get addressed if you're recommitting to each other every year. I think that's a beautiful idea.

I loved that. I was like, okay, when we talk about relationship lists, somewhere that's on mine. When I find someone I mean, all right, we'll just renegotiate every... You can take me on a trip for our anniversary and we'll see if I'm willing to give you another year. I love that. That kind of commitment I'm willing to make. Yeah. I love the idea of the trip. Yeah, yeah. Who doesn't want a good trip? I know, seriously. I think that every couple should take a trip every year away from the kids though too. Oh yeah.

See I think I'm in a different place now. Like I used to think things about kids. Like I get people in different ways, but I don't... how... like my kids are adults now. I know mine. I'm not saying that they won't go on a trip, but you're an adult. I'm not paying for you anymore. Very true. So you want to go on the trip, go on the trip. Yeah. But you can pay your own way. Absolutely, no question. You're free to stay at a hotel with me, but yeah. Different... we're in different places. Yeah. Yeah. And I got... I'm the grandma. So that's still... I'm not ready for that. It's so much fun. Seriously. My mom says that grandkids are the reward for not killing me as a teenager. And I put that woman through... I might have been headstrong. Don't know where I got that. Just like my mother. Oh my goodness gracious.

You... well, you know, you're awesome. Thank you. I appreciate that. I think you're pretty cool yourself. Thank you. Appreciate that. We're just gonna sit around and awesome each other, you know. Yeah, you know what? Everybody needs that. I know, seriously. I actually think a lot of times, like I know we're talking about dating, but I think a lot of times it's like friends.

There are so many friends that don't really celebrate people's successes. We all know who they are. I just keep those people over there now. Yeah. I used to have a lot of those in my life that really weren't happy for my success or "You can do great, just not better than me." Yeah. Right? And those relationships are actually way more detrimental to ourselves than we think it is. So nowadays "I only surround myself with the awesome squad." I love that.

I do. Again, everything has a varying degree. I try to think about it as the seesaw. I understand. I always think like I'm willing to give somebody a one-off. Those happen. Yeah. And you know, I'll get there with dating too, but like a one-off, okay.

You're allowed a mistake, but "if you make the same mistake twice, you didn't learn anything." 

Yeah, you know, that and I think that's really interesting because in relationships, right, when something happens, right, and then it happens again and the person says they're sorry, but then they repeat the pattern. Right, a behavior. Were they really sorry? Because they didn't learn the lesson.

Oh, they might be sorry, but I always think about a part of life is just a little bit of sacrifice and discipline. Like if you know there's a consequence that you don't like, then you're not going to do it. Right. Yeah. And if somebody is repeating a pattern, maybe it's not that they're not sorry. Like they might be sorry. They might know their actions are wrong. They just don't care enough to do what's right. They don't have a little bit of... This is just my view. Yeah. I think, you know, it's interesting. When I have my relationship with my husband, we have certain things that we do. Like when I got here today, I sent him a text that I arrived here safely, right? That's something that's really important to him. If I failed to do that, then I'm not caring about what's important to him. Yeah, that's part of it, you know. Uh and I think that a lot of times people don't do what they need to do in the relationship because it's not important to them, but it is important to their partner. And those kinds of things harm the relationship when you don't understand that your partner needs those things.

Well and it might be a little bit again that like self-sacrifice like, okay, this may not be important to me, but it's important to my partner. So I have to accept it. Exactly. All right. And I think there's a thing that but like if I know it's important to this person and as simple as sending a text, like it's not gonna take that much for me. I just have to sort of train myself to do it. If I'm constantly forgetting, you're gonna let that person's brain make up a dramatic story. Are they cheating on me? Were they in a ditch? Kinda like my mom used to do when I was a teenager. And granted we didn't have cell phones then, but if she didn't know where I was going, yeah, that's what mothers do. Exactly. That's a partnership too.

Yeah. So let me ask one more question as we get to the end here. Yeah. If someone is going to go searching for love and wanting to make that connection, what is the one piece you would give them today that they should start doing to get in that direction without it being overwhelming? Like what is one baby step they could take? I would say read my book. Okay. That's a good one. You know, my book is a comprehensive guide of how to prepare. And then the how-to guide, right? And there's a good flow to your book. Thank you. I appreciate that. It's comprehensive. And um I would say start with that and do the exercises in the book. "It will not take you that much time to do it, but you will be light years ahead of other people that are out there dating if you do that work." I think that's a big one. It's like you have to do the work. Maybe choose what work you feel comfortable with doing today, but you gotta keep it moving. Yeah, absolutely.

Awesome. Well I am so glad that you joined me today. I could be here all day talking about this stuff. I know we could. Well, everyone, thanks for joining. Remember, karma's real, energy is contagious. Check your vibes.

So you can get my book, Soulmate Quest, a Matchmaker's Guide to Find True Love, on Amazon. It's super easy and it's available in multiple formats, including Kindle. I now have my workbook available for purchase on my website, justcalljenna.online. There's a shop button. You can purchase the workbook that shows you seven days of how to start resetting your stress level. It's downloadable. You're not getting some book. You can just download it and print it on your printer or use it on your phone. For many of my listeners, I've been getting emails and comments about people asking how to get started without choosing to have coaching or lifelong sessions, if you will. Purchase it. "It will give you the momentum to get started." And then if you need more support, please reach out to me. All my contact information is on my website.