Episode 221 - Dating, Surrender, and Our Journeys with Jackie Glaser (Part 1)

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In this episode, I’m joined by the amazing Jackie Glaser—psychologist, educator, and transformational coach—for a powerful conversation about dating, marriage, and emotional healing.

Jackie shares her own journey from psychologist and Today Show guest in Australia to deep Torah learning in Jerusalem, and how she now helps women tune into their inner world to unlock clarity in dating and life.

We explore:

 ✨ When a relationship goes too deep before marriage

 ✨ How sure someone really needs to be before they say “yes”

 ✨ The difference between dating to assess and dating in a relationship

 ✨ How these experiences might play out beyond the chuppah Jackie answers from the dating perspective, and I chime in from the newlywed side—it’s real, honest, and packed with gems for wherever you are in your relationship journey.

🔗 Mentioned in this episode:

 👉 Learn more about Jackie: jackieglaser.com

 👉 Follow Jackie on Instagram: @datingbyjackieg

👉 Jackie and her husband Aharon share their dating journey on Stories of Hope YouTubeMarried at 44, Baby at 50: A Story of Faith & Resilience | Jackie & Aharon Glaser | Stories of Hope 

 👉 Explore my resources for newlyweds and beyond: kaylalevin.com

💌 Subscribe to the podcast so you don’t miss Part 2, where we dive into dating mindset, emotional triggers, surrender, and what to do when your spouse changes.

Transcript

[00:00:00] Welcome to part one of a powerful conversation with my friend and colleague, Jackie Glaser. Jackie is a psychologist, educator, transformational coach who helps women step into dating and marriage with clarity, emotional intelligence, and deep inner alignment.

[00:00:14] Jackie and I structured this conversation around five questions. She speaks from the dating perspective, and I chime in from the newlywed side. In today's episode, you'll hear her incredible backstory, how she went from the Today Show in Australia to seminary in Jerusalem, how she discovered a path to personal healing that now supports countless women.

[00:00:31] We cover what kind of depth is too much before marriage, how sure someone needs to be before they commit. And what the dating process is really meant to be all about. Whether you are dating or already married, I know you're gonna get a lot of value outta this conversation, so check it out. Let's jump in now.

[00:00:48] See you on the other side.

[00:00:50] 

[00:00:51] Welcome to How to Glow, where we get real about building the marriage of your dreams. I'm certified coach Kayla Levin and I help married Jewish women go from surviving and overwhelmed to thriving and connected through practical tips, real life inspiration, and more than a little self-awareness along the way.

[00:01:09] 

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[00:01:10] I'm really excited about this idea

[00:01:11] because. We know each other. I know you're brilliant and I knew this was gonna be a great conversation. All right, Jackie, tell us if anyone does not know who you are, how do you like to introduce yourself? How do you like to be known?

[00:01:24] I just say I'm Jackie. I mean, I don't, I don't do this, you know, I don't introduce myself like, duh.

[00:01:30] This is, um, I was born in Montreal. I was raised in Australia. Father was a Holocaust survivor, so let's get as far away as Judaism from Judaism as possible. Mm-hmm. Um, which is why we were there in a very non-Jewish environment growing up. So I had nothing to do with Judaism except for

[00:01:50] Chanukah presents and some semblance of a Seder.

[00:01:53] That's it, I think. No Rosh Hashanah by Yom Kippur. Nothing. So that shows how far out, um, and became a psychologist, wanted to help the world, wanted to understand how people grow and tick, and including obviously myself and um, I. Then my brother started becoming observant through a birthright. Stayed on at Aish and I got worried because he started becoming quite extreme.

[00:02:19] Shomer Shabbos, Shomer Kashrus , , I freaked out, said You joined a cult. But deep down, I knew I didn't know anything about Judaism and I was Jewish. So with those tensions running for about a year or two, eventually that propelled me to Israel to visit him at Aish, and he was thrilled and pushed me in front of all the rabbis and was like, go for it.

[00:02:36] You know, took them on. One of those being Rabbi Keleman, who became my rabbi later for many years, and, uh, ended up going to Israel for a visit. Um, you know, a visit that turned into eight years. That's the short version. Yeah. Um, you know, I had a psych, I had a career in psychology, private practice. I was on the Today Show.

[00:03:01] I walked off the Today Show to go to Israel. Everyone thought I was committing career suicide, which I really was, but I didn't care 'cause I'd already made it and that could, that wasn't it. I knew that there was more to life than that success. And, uh, and I was very young. I was in my, I was twenties, in my twenties at that point, but by the time I got to Israel it was 29 30.

[00:03:18] So I knew nothing about Judaism really. Deeply until 30. And uh, and then I ended up teaching at Neve Yerushalayim, for two years after being a student there for many years and was on faculty and then got sponsored on a green card to go to New York for kiruv Outreach for what's now called Olami, which I was so grateful for.

[00:03:40] Worked there for 13 years, running programs, teaching counseling, you know,

[00:03:44] and that's how we met.

[00:03:46] That's how we met.

[00:03:47] Um, and then I wasn't getting married and wasn't getting married and wasn't getting married, which is also one of the imp impetuses to move to New York. And, uh, you know, I made deals with God and said, if you get me married, I'll help shidduchim. I'll help dating, I'll help, you know, whatever it is, if God needs my help.

[00:04:03] But I, you know, you do deals and bargains with God when you're in a desperate place. Hmm. And, uh, eventually I met my husband through another crazy story, got married, moved to LA with him. He's an LA guy, and that's what I do full time now. I realize it was a huge, huge need, uh, in the Jewish world for deeper work.

[00:04:22] I don't, it's not really dating, coaching, I don't know what to call it. I, I thought of dating surgeon, but no one wants surgery, so I don't think. I don't think I should call it, but really what I help people do is get to the root of what's blocking them and teaching them through somatic work, through IFS, through different techniques and principles.

[00:04:40] It's not therapy. It's a course that educates and empowers people, single women particularly, to tune into themselves at a deeper level and know what's really going on. Rather than just giving you tips and strategies, even though those are helpful, they don't change how you feel. Deep down you could say, I need to, I need to date with more self-worth.

[00:04:59] And you're like, yeah, I know that, but how do I get that self-worth? Like how do I actually feel that? Yeah. I teach people how you actually change that feeling, which happens at a subconscious level. It's visceral. It's not a, an idea, it's not a cognitive belief that you say to yourself, you know, that's why mantras and affirmations and all these things work very limitedly because you have to get to a deeper level too, within yourself.

[00:05:21] But people don't dunno how to do that. So that's what I teach them. And I teach married women also, but I just focus on the singles mainly 'cause it's mm-hmm. We all need this all the time. It's about how to process yourself, how to transform, and, uh, and that within that we do, we talk a lot about, and we, we practice experientially surrender to Hashem, surrender to your own reality.

[00:05:41] Surrender to Hashem's decisions is surrender to Hashem's love for you. There's so many levels of this exercise is mechanism called surrender. And that's really what I spend most of my time doing now. Um, and I love and I've had to. Really be forced to practice it myself in many ways, both with getting married and with having a baby, which we now have a miracle little baby Ariella, who's now just four months.

[00:06:02] Um, and so that's what I do now full time. I have a team, I have other therapists and coaches that work with me, and I have a whole initiative called The Inner Circle to help singles to really get to the incredible, incredible, that was a long,

[00:06:16] that's like whenever we get a chance to do this work, right?

[00:06:18] Because. I'm sometimes seeing this work on the other side of the chuppah. Right. And it's, it's just work. I, I mean, I wonder if it's also just developmental, meaning we're not really gonna do that work unless there's a crisis. I'm thinking. When we're teenagers, when we're right, we're still figuring out kind of how to get our feet underneath us.

[00:06:37] It almost reminds me of what you're saying about your story, about like, you made it in your career and then it, then you have that reality. Oh, it's not it. Like we need to get that. Oh, this wasn't it. I, I always say how it's, to me, how many people I meet here who made aliyah after buying their dream house and we're one of them.

[00:06:51] Wow. Wow. And I think it really goes together. It's like you buy your dream house and then you're like, this, isn't it? Oh, that's the thing I was holding out for.

[00:06:59] Yes.

[00:07:00] And now it's happened. And now wait. There's something still inside of me that still needs to be fixed. So if it's, you know, I'm, I'm ex you know, it's amazing if someone's doing this even before getting married because then they're, they're learning that work.

[00:07:14] But sometimes, well it happens. I got married it

[00:07:16] through that way, what you're saying, and it also happens the other way through adversity. Meaning, so if you go through, God forbid, some real pain, like my dad died suddenly when I was 17. Yeah. And it was like a bomb went off, you know, like, 'cause he was my rock and my mom wasn't as well.

[00:07:31] Then you're for, then you search as well. Yeah. So it's like either through the pain or through have it all, and this isn't it. It's interesting. Yeah. Yeah. Right.

[00:07:40] Like Hashem

[00:07:40] can get us there, however, right. However he wants. Yeah. Yeah. A hundred percent. Okay. So , as you said, , you do work with people who are married, but I'm gonna use you as our, a dating expert.

[00:07:51] Um, for this episode, I do have a lot of people that listen who are dating, which I love because why not get this information even beforehand? That's, but I think it'll be fun to see how different the approach needs to be when we're in a dating. I call it dating mindset versus marriage mindset, right? Yeah.

[00:08:10] When we're looking at, from dating, and I always say to people, like very often people will say to me, well, you work with all these newlyweds. Can you help me with a, and I'm like, I am the worst person possible. 'cause I just keep seeing things work. So like I can't, I don't know any red flags. I don't know when you say no to something, because I'm on the other side where my, I'm in marriage mindset for all my clients.

[00:08:30] How do we make this work? Right? I, I don't really go there, so I'm very curious to pick your brain, just to hear where you go. So, these are five things that have either come up in coaching have people have asked me that I see with the students that we get close to. So the idea is I have five questions here and you are going to give your take, and it doesn't have to be like the authoritative, answer, but what comes up for you hearing this question or this concept as a person who works with women who are dating.

[00:09:00] And then I'm going to respond to it as somebody who works with newlyweds. And we're gonna,

[00:09:06] and these five specific questions you picked because they're really common or you see them a lot or,

[00:09:13] Yeah. I Meaning they, they're they create conflict or Yeah. They're common or they're, yeah, they're definitely coming up.

[00:09:18] Perfect. Yeah. So curious. Okay.

Question 1: Can a relationship go too deep before marriage?

[00:09:21] So the first one is, can a relationship go too deep before marriage?

[00:09:27] Another way of saying this is. What are things that could be dealt with during the dating process in terms of working out your relationship and are there things that need to, that are like this is more marriage work.

[00:09:39] Wow.

[00:09:41] It depends what world you're dating in. If we're really applying this to the observant from Yeah.

[00:09:47] Orthodox. Which is dating then is a different thing. Dating is I wanna get to know this person enough to know whether I wanna commit to a relationship with them. It's not having the relationship itself, which is very different to if you're more modern or secular or traditional, very different. One is I'm having the relationship my with the person until I get to a place of comfort within the relationship itself that I say I wanna commit.

[00:10:16] The from Orthodox system is not that at all. That's why they can do it so fast. There's certain things that I'm looking for that we know what the raw materials are to have a good marriage, we know what they are. It's not a complete mystery. We know what the raw materials, we need to have a good marriage overall.

[00:10:32] We know, that's why I say to my singles when they're panicking and freaking out and they dunno whether this is the right guy. I was like, wait, wait. Slow down. We know what these are. We know what you need to have in place. For it to be. All the raw materials you need to have a great marriage. That's all you can do when you're dating.

[00:10:47] And so that's what you do when you're dating in the shidduch world. I'm looking for does this person, and not just the person, but the dynamic between us, have the raw materials that it needs to have for me to then take the leap and commit. 'cause there's always a leap, but it's an informed and educated leap. It's not just a leap into the abyss if I'm not, yeah.

[00:11:08] So there's always a leap of commit and, and, and assuming that there's gonna be lots of things that come up that I don't know. 'cause the biggest fear a lot of singles have to me, that they tell me is I'm gonna wake up and he's gonna be a different person. I'm gonna find out all these things about them, and I'm, and guess I go, yes, you will.

[00:11:23] You will expect it. Expect it. You know, your spouse after dating them all of three, three months or two months or whatever it is for you, you only know, uh, 20, 30, 40%. Of course there's gonna be other things, but once you realize that those things are normal and they would come up in any marriage, like the deeper layers, right?

[00:11:44] The subconscious stuff, shadow side, and all this stuff and that, that's what marriage is. Marriage is working through all that stuff, as long as it's within normal range. Not abusive range, then that's normal. That's okay. Like do you have the raw materials to make it through and to make that work? And so to answer your question with that as a backdrop, if my goal is to assess do I want this relationship, then yes, there is definitely to much depth that someone can have.

[00:12:13] When you're dating in that system, because what happens is it, and I've seen this, I've seen this numerous times, it shifts from assessing, do I wanna have this connection? Can I have a connection with this person? Do they have the same values? Are we aligned and compatible? Are we going in the same direction?

[00:12:27] Do I feel myself around him? Am I attracted, does he have good character? Like all the things we're assessing and they move into the relationship mode without the commitment. And so now they're in the relationship mode working through and some of the deeper, darker stuff is coming up, but there's no vessel to hold them in.

[00:12:45] There's no commitment. There's no marriage, there's no, if they're shomer negiah, there's no touch, which is absolutely. Han it's very, very hard to have to deal with some of the deeper, harder, intense stuff and not have touch as a, as a glue and as a connector. Yep. And that's 'cause we're not meant to do that.

[00:13:05] It's not normal to be shomer negiah and have be dealing with all this intense inner stuff. And so obviously people break it. Which is very typical, they do break it because of that. It's 'cause it's too hard. So rather than protect themselves in advance and not put themselves in that position, whatever position that is, whether it's too tempting and too, you know, too difficult to and.

[00:13:27] So yes, I think that there is a level where people are scared to commit. So they keep going with the relationship and then they get into the marriage mode of like, we're in a long-term committed relationship, like boyfriend, girlfriend, but we're in this weird limbo where we're not committed and maybe we're not even touching, and that is really way harder.

[00:13:47] So I would say not to do that. I would really recommend get outta that. Either move forward into commitment or. Away and say, let's come back together when we are sure that we wanna move forward and like, actually not continue dating that way

[00:14:00] because you're not able to be clear about, am I getting this right?

[00:14:04] You're not able to be clear about the decision as much because you're no longer doing that assessment phase. You're already in the work.

[00:14:11] Well, there's two things that happen. One is that the intensity gets too intense because yeah, you don't have the vessel, and so the intensity can be nearly.

[00:14:21] Exaggerated because there's an anxiety, because there's no commitment. The commitment takes away the anxiety. Like, we're in this together, we're safe.

[00:14:29] Yeah. Okay. Yeah.

[00:14:30] If you're not in this together and stuff's coming up, so as you're trying to work through stuff, you're always, there's this little part of you analyzing, oh, this is deal breaker.

[00:14:37] Is this a deal breaker? I don't know. I don't know. I dunno. What does this mean about the future? Ugh. Yeah. And you get so scared because of what you're seeing, that you're always like one foot out, potentially. Rather than No, no. Jump all the way in. It will be easier and you'll feel safer 'cause you're in.

[00:14:52] And so that's, it's like trying to be in without the vessel holding you. It, it's just, yeah. Yes. I think that, that it makes it more intense. Yeah. And then you have more doubt, which like you said, means that you're not as clear about the decision. Right.

[00:15:07] So it's very so interesting to hearing you say this.

[00:15:08] 'cause again, this is not the people that I'm working with. And so when I think about, when you say like the marriage holds you, which I think it does, and I don't, I'm not comparing before and after, but what I see so often with newlyweds is it's like the intensity becomes, oh my gosh. And this is forever, right?

[00:15:25] Like every issue that comes up, it's, and this is forever. I just committed to this, right? So there's like this. New kind of intensity on the other side as well, which I just wanna say is very normal. That makes a lot of sense. And it's the work that we do in shana rishona, which is being, it's almost like being able to feel that container holding you like Yeah.

[00:15:45] The container happened, but doesn't mean that you, it's almost like with a toddler when you're like, here's the boundary. And they're like, really? Let me push here. Let me push here. Let me push. Oh really? Oh, there really is a boundary there. It could be a toddler, could be an adult, but either way.

[00:15:57] And I feel like we're doing that in a way during shana rishona and also we're like rattling the cage. Will this really hold me? Whether that's emotionally we should, I'm not encouraging it. I'm just saying this is kind of the emotional experience, right? That a lot of, that a lot of couples are having.

[00:16:11] And also, what's

[00:16:12] the question? What, what's the question applied in your, with married couples? Like what would Yeah.

[00:16:17] Right. So I think what I see is that sometimes, like you can see very much with newlyweds how much stuff they're bringing in just from the engagement process.

[00:16:27] Hmm.

[00:16:28] Right. And so sometimes like they come in and all the work we're doing is just cleaning up what happened during the engagement.

[00:16:36] Oh, wow. It's like this happened and this happened and it's, I think it what you're saying, sheds a lot of light on that. It's obviously by the time I'm working with them, I can't do anything about that. They're now, they're married, right? So they finally did make that commitment.

[00:16:46] But we still have to go back and heal that, right? And say, okay, so what did we, how are we telling, how are we narrating that whole experience to ourselves? Is that, and then how is that being carried now into your marriage? And you just need that space to kind of air it.

[00:17:03] Like all those fears that were just kinda okay, well now I'm married, so let me just not look at that. I don't wanna look at that. But then that never works.

[00:17:11] What to that You mean the stress that happens through the, let's say

[00:17:14] the, oh, but I had these questions about him all along. Like, I, I wasn't sure all along.

[00:17:20] This is actually the next question I'm gonna ask you. So maybe we'll just let it be a straight one, which is

Question 2: How sure should a person be before they get married?

[00:17:24] how sure should a person be before they get married? Oh. So that's one of the ones that comes up for me all the time, which is they'll say well, but I, I don't know, you know, it was only 80%.

[00:17:32] I was only 70%. I, I, I did have these questions, so what does that, it's too late by then, mean for me now. It's too late. By then, by the time they get to you, they, they're married. They are married. They are married. But if that's what they're thinking, that's gonna have a big impact on how they're showing up in their relationship.

[00:17:49] Yeah, yeah. Yeah.

[00:17:50] 80 20. 80 20. I tell all my single women, I tell them 80 20, like, you'll never get a hundred percent ever. So 80% of the relationships should be great, should be aligned, should be fun, should be compatible, should be easy, should be, you know, all these wonderful things. And assume and expect 20% will not be, will be a gap, will be a bridge, will be difficult.

[00:18:13] Well, you'll see flaws, you'll see this, you'll see that at least 20% before marriage. Like, oh, they're like, phew. You know? That's great. Now, I like, once you have realistic expectations, you know, how many times do you meet someone that's 80% aligned with you? It's, it's rare. Yeah. So, so 80, 20 and then when, so, so then when something comes up you don't like, you go, oh, that's part of the 20.

[00:18:36] And I'm go, and I'll say, what's part of the 20 that he has to deal with? Yes. Thank you. Hello. I'm like, what? What? What do you mean? I say, what flaws is he gonna have to deal with in you? Yeah. Oh. Oh. I don't know. I haven't thought about that. Right, exactly. Right. But he's gonna have to, you know, someone pointed out on my, on the Meaningful Minute podcast, a floor I was doing with my husband on, on a comment publicly, you know?

[00:19:01] Oh wow. And I wrote back to her publicly. You got me. You're right. I, I said that's one of my things I'm working on. You know, I am working on this issue and, uh, you know, your, your flaws are there for everyone to see. You gotta own it and come at it with compassion. And I said it's where work's in progress.

[00:19:19] I did say to her, I'm cur, it's curious to me that of all the things to comment on. You would choose that thing to point out publicly, but with the story and the whole thing that happened, it's like that's the thing you're zoning in on. You know, it's worth you being curious about your own s self, that that's what you're choosing to focus on and highlight on, you know, but we're all, we've all have flaws.

[00:19:37] Let's stop with the pretending it's bad and it's, it's not okay. And the more you can own it, the more you can work with it. It's okay. It's okay that some people have flaws and it's okay. That your spouse has flaws and your date has flaws. And people, I think, are so scared of making the wrong decision that they're looking for the flaws and the, when they find an evidence of a flaw, they say, see, I should run away.

[00:20:01] See, that's proof I should leave this. So I don't know what you do when that you are on the other side and they're married. Mm-hmm. Like what do you tell

[00:20:13] them? So the first, I mean, the most basic thing is. Just helping them see, like this thought is a train and where is it taking you, right? So when you're in that headspace, you're tuned into that channel.

[00:20:26] Let's just actually look like, let's just take a moment and explore. How does it feel? How are you showing up when you're in that headspace? And then what's that actually creating? And every single time there will be in some way that will translate into she's not showing up in the relationship or she's not giving him the benefit of the doubt.

[00:20:41] Like there's a disconnection from that because. That's a logical, that's just a logical flow, right? If I'm thinking, maybe this isn't right, I'm not going to be going all in and connecting. So when she's able to see that, I find that sometimes just understanding the mechanics of our thinking can, it's not the, it's not the, it's not the only work, but I find that sometimes it can kind of bypass, for instance when I was first working on like self-confidence or just the way that I was talking to myself and just trying to be a little bit more compassionate, I wasn't able to get there in the beginning from a place of, but I'm a human being and I deserve a certain level of respect. I couldn't get there, but when I just looked at like the train and I was like, Ew, I don't like what I do when I talk about myself like that, I don't like how I'm showing up.

[00:21:29] It's not working, it's not effective. So then it allowed me to get there, and then I was practicing that behavior long enough that I was like I was getting those own my own messages, right? Oh, if I'm treating myself nicely, then maybe I'm worth treating nicely. So that I feel is, that's usually where I like to start with people, is let's just get some self-awareness, right?

[00:21:51] And realize that there's so many different, it's not about. Say if your reality is Grand Central Station and there's 40 trains, you could get on 40 different realities, ways that you could narrate this experience. And then someone comes along and they're like, there's an invisible train over here, and it's led by unicorns and it's called Everything's perfect.

[00:22:09] You're not gonna jump on that train. So the same thing with our thinking. We're not gonna believe a thought that's completely out of left field. That is, it makes me crazy when people are trying to do mindset work and they're like, just believe everything's great or you're the best. No, we won't do that.

[00:22:23] But it doesn't mean there aren't so many other options of also true things. Right. That we can be looking at and we can be noticing how we show up.

[00:22:31] Yeah. And zooming out to the bigger perspective, that includes also you and your flaws and the dynamic, not just zeroing in on someone else's flaws as an isolated thing.

[00:22:40] Right. That's the dan l'kaf zechus issue. Right. Like that for all of us all the time, everyone that we shouldn't be zoning in on someone's flaws 'cause that's not who they are. That's just a flaw. They're much bigger with multiple layered, complex beings, you know?

[00:22:55] And it's amazing how freeing acknowledging your own shortcomings can be in this.

[00:23:01] Yes. Like when you're able to go to a place of Oh, right. I also have those things then when it's, it's amazing. Yeah. And it just allows this to be right. We're just humans married to other humans, like at the end of the day. Passion. I wanted us to be melachim, we would be, we're not, we're supposed to have, I

[00:23:19] call it matching.

[00:23:20] Matching. When you're judging someone else, you find, actually find the part in you that does the same thing when you match yourself with someone else, even just internally, it takes off the judgment. It gives you like brings in compassion more. Because we're so to be compassionate with ourselves.

[00:23:33] Yeah. Yeah.

[00:23:35] Okay, great.

[00:23:36] Okay, so that was part one. I hope you loved it. And part two, we're gonna dive in even deeper into how our stories around dating affect our marriage. What to do when your spouse changes, and how surrender becomes a spiritual and emotional superpower. It's amazing. There's even more where this came from, and you will see it next week on the next episode.

[00:23:56] See you there.