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Jillian on Love

10 Aug 2026 · 41m · 9 chapters

Episode artwork

The Moment You Need To Stop Pursuing Someone

In short

Advice on stopping pursuit/chasing in dating, interpreting inconsistent behavior, setting boundaries, and recognizing emotional readiness for real intimacy.

Guests

No guest(s) appear; the episode features Jillian Tarecki giving advice to two listener scenarios and answering a listener question.

Guest backgrounds (listener cases)

(1) A woman (age 34) dated a man (47) for ~3 weeks after a first-date sleepover; he became inconsistent after redundancy/job stress. (2) A woman (34) is dating a separated/divorcing man (47) for 4–5 months; he remains married, no attorney involved, and there’s no progression.

Key claims

“If he wanted to, he would” often applies early; sleepover/sexual intimacy can accelerate casual dynamics; sexting without being asked out can lead to exploitation; you shouldn’t tiptoe around someone’s divorce/separation—direct communication and standards are required; emotional maturity shows prioritizing “we,” staying engaged through issues, and making space for another person.

Notable examples

ignoring texts after a first-date sleepover; inviting her over but not asking to see her again; five months of dinners/sex with no labels and monthly “where do we stand?” questions.

Written by AI. May contain mistakes.

Chapters

1:16

Setting Up Today's Advice

Jillian introduces the topics she'll address regarding relationships and rejection.

“Hey everyone, welcome back to Jillian on Love.”
1:50

Listener's Date Experience

A listener shares her experience with a guy after a first date and her confusion about his behavior.

“About three weeks ago, I went on a date with a guy.”
4:52

Jillian's Tough Love Advice

Jillian offers advice on recognizing self-worth and understanding relationship dynamics.

“So I have absolutely no moral judgment at all about what people want to do versus not do on a first date.”
11:04

Understanding Sexting and Expectations

Jillian discusses the implications of sexting without commitment and the confusion it can cause.

“that you never want to do is get into a sexting exchange, like get into sexy texting with someone who's not asking you out.”
14:00

Understanding Relationship Stages

Explore how different life stages affect relationship dynamics and emotional maturity.

“plays a role in this because stage of life plays a role.”
18:06

Intro to Jevity Sponsorship

Learn about Jevity, an all-in-one precision health membership designed to improve health.

“Testing, clinician-built protocols, personalized supplements, and prescription therapeutics all in one plan.”
19:36

Navigating Complex Relationships

Discuss the challenges of being in a relationship with someone going through a divorce.

“I have two children who are teenagers 15 and 12.”
28:01

Empowerment in Relationships

Learn the importance of taking charge in your relationship dynamics.

“But in this very delicate place of we're not quite in a relationship, but we're not not in a relationship, you got to have a voice and not say and not look to him anymore for leadership.”
32:41

Recognizing Emotional Maturity in Relationships

Identify signs of emotional maturity and readiness for intimacy.

“or whether they just want the concept of a relationship without the depth?”
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Transcript

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0:00Hey, everyone. I have a really big announcement. My new book, Rewrite Your Story, How to Step into Your Power and Get the Love You Deserve, is officially available for pre-order at JillianTarecki.com book. Our past and how we feel about ourselves determine the way that we love and what we believe that we are worthy of. And inside, you will learn real practical steps to heal old wounds from childhood, overcome attachment issues, and break painful relationship patterns that are getting in the way of your happiness. This is the most personal and practical work I've ever created, and it will truly change your life.

0:47It is more than a book. It's a manual or a guide for healing, for secure relationships, for self-worth, and ultimately for letting go of the parts of your past that are continuing to haunt you. So again, it's available for preorder at JillianTarecki.com book. and I thank you all for being here and for your support.

1:16Hey everyone, welcome back to Jillian on Love. Today you're going to hear me give advice on someone who is starting to get rejected by someone who she went to bed with on the first date. Yet someone who has been seeing someone for five months who's getting a divorce and the relationship is not progressing. And then I also share what it really means when someone is actually ready to be in a relationship versus not. So I think you're going to really love this one and I can't wait to hear the comments about it. Hi, Jillian. About three weeks ago, I went on a date with a guy. It was our first date and we spent hours together.

2:01We spent the night together. There was a little bit of intimacy. um we'd been talking for a couple of weeks before that a week or two and I knew we were going to have a good time because we were getting on really well and we did and on the night he was like I do really want to see you again he he invited me out with his friends the next day and then the next day kind of came and it didn't happen he didn't invite me out again with his friends he just went out with his friends he didn't ask to see me but we continued texting and then towards the end of that first week he he said that he'd been made redundant and it affected him and his team and so he was juggling a lot and he would get back to me when he could about something we were talking about and I'd said okay well do you want to see me this weekend and he's like I'll get back to you when I can and he didn't so then we started texting again that weekend um because I think I started the conversation oh I asked him how he was and he said it's been one hell of a week and he was just hanging out with his housemate and this was the Saturday now I'd offered him a Thursday or a Friday to see me so we got to the Saturday and he was just like oh you can come around tonight and I was like no you had your chance to see me I'm actually busy tonight we were texting a little the next morning and it was kind of sexual and then nothing for a whole week I text him on Saturday sent him a photo with something related to the date like a jokey thing and he read it and ignored me until today this morning and he's texting me again basically saying like following up playfully like asking me a question about it and then basically said like sorry for the quietness he's going through a lot at the moment he's juggling a lot um he's got quite a lot going on and I just think at what point do I think okay well he's obviously not prioritizing this and engaging with this at the moment why is he keeping the door open right now um and at what point do I stop giving leniency because of his situation and think well actually it's been three weeks he hasn't asked to see me again um yeah like what's next for this is he trying to keep it casual okay so I'm going to give you some tough love but I want you to know that I'm giving it to you with the utmost compassion and I don't want you for a second to get down on yourself or to be upset with yourself that you messed anything up because there's nothing that you messed up and there is absolutely nothing special about this guy.

4:53He's a total stranger, okay? But I am gonna give it to you straight. So I have absolutely no moral judgment at all about what people want to do versus not do on a first date. you decided to spend the night with him you said there was some intimacy I don't know if that means kissing I don't know if that means sex but still even if there wasn't actually intercourse you slept over he slept over at your place and that's very intimate and it's a first date are there people who have spent the night together on the first date and ended up getting married Absolutely. Like there's no, like there's no right or wrong, so to speak.

5:49That said, the problem with that, and I am going to get gender specific because it's, it is pretty gender specific. It's not, it's not a hundred percent, but most women, not all, and certainly this is not all men, but most women, when you like someone and you have a good time and you're attracted to them. And when she spends the night with this person, she is going to want more of this person. And that's just not always the case for men. So again, I have no judgment about it. All I ask is for people to be honest with themselves and say, if I were to spend the night with this person and really enjoy myself, and that would be it.

6:45I might get ghosted. I may never see this person again. I might see them again and decide it doesn't work, or I might see them for a few weeks and then they reject me, whatever it is. Am I going to be okay with that? And I just think that for most people, if they were to be honest with themselves, they would say, no, that would be like, that would stress me out. And that is perfectly okay and perfectly human. Human behavior is actually very complex. And so this trope of if they wanted to, they would. If he wanted to, he would, doesn't really work when it comes to actual relationships because most people in relationships are doing what they can.

7:33based on their emotional capacity and their skill set and their and and whatever their physical state is in the moment whether they're exhausted or they have energy when it comes to early dating this idea of if he wanted to he would actually is true most of the time if he really wanted to see you him being busy with work really wouldn't be a deterrent and if it were he would call you and he would say I really like you here's when I want to see you the next two weeks or whatever are really insane with work but let's put something in the books for when we're going to see each other again. That's what he would do.

8:31And what I really want to say, and of course this is a message for everyone, but I see this overwhelmingly more in women, is you have to really see your worth and not chase anyone. And you've been doing a little bit of chasing. And I think it's been totally innocent. And it's because, and I hate to say it, but there is a little bit, there's a dance. I don't want anyone to play games. I don't want anyone to pretend like they're not interested. I actually want people to be more honest about being interested. But there is a way to be vulnerable and say that you really, and to convey and reveal that you really like someone while simultaneously having boundaries and standards and not chasing.

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10:32Need to hire? This is a job for Indeed sponsored jobs. And listeners of this show will get a$75 sponsored job credit to help get your job the premium status it deserves at indeed.com slash podcast. Just go to indeed.com slash podcast right now and support our show by saying you heard about Indeed on my show. Need to hire? This is a job for Indeed sponsored jobs. So one of the things that you never want to do is get into a sexting exchange, like get into sexy texting with someone who's not asking you out. Because I want you to protect your dignity and I want you to protect your body and yourself.

11:26Someone doesn't get to do that with you unless they are actually taking you out. And look, are there scenarios? Because, you know, I know that there are scenarios where we feel empowered to have that kind of sexting exchange and we don't care and we want to make it casual and sexy anyway. More power to the person who wants to do that. But your question conveys someone who likes someone, wants to date someone, and is very confused about someone's behavior. So this guy, it's more than likely not going to work out with him. And the reason why he is still keeping the door open is because he can, because he's not quite sure.

12:16He may want to see you again, but maybe not. You mentioned he just doesn't seem to be prioritizing this. And your instinct is right. So knowing that he's not prioritizing you or getting to know you better or prioritizing some sort of engagement, you know, between the two of you, how does that make you feel? Because I'm sure it doesn't feel great. And why then are you continuing to ask to see him? You know, it's part of it is knowing our worth. Part of it is having more confidence in dating. And part of it is not succumbing to the fear that all of us have on some level that we're going to be alone or we're not going to meet someone or that we're not good enough.

13:13The resilience and the conviction that it takes to not succumb to that fear is big. And it's so important. If he wanted to, he would, he would ask you out again and you asking him out and then him making excuses and then texting you again. It's just, it's, um, it's not, it's not what you ever want to do. It's never going to feel good for you. And, you know, why he's keeping the door open is because you're a maybe. And in the moment when you spent the night together, in the moment, he was feeling it. He wanted to see you again. And then once there was distance, it was like, oh, well, you know, I'm busy with my guy friends.

13:57I don't know how old you are. And I think age plays a role in this because stage of life plays a role. So I don't know where he is in his stage of life where like hanging out with his boys and like work is more important than being in a relationship. Or he's in a stage of life where he hasn't reached a level of emotional maturity that so many people are lacking in the dating world of all ages to just be able to say, hey, you know, I'm not quite sure if this is the right connection, you know? And the thing is, is that I wish that people would do better. I wish that people would not string other people along, but you know, a lot of people are selfish and they are not considering other people's feelings.

14:41They're only thinking about their needs and their needs are, you know, when I'm in the mood, I'll sex this person. You know, when I'm in the mood, maybe I'll go out with them again. And he He didn't even ask you out again. He invited you over. It's like once you slept over, he didn't even think, let me treat this woman with even more respect and take her out for a meal or do something nice for her. It immediately went from first date to something casual.

15:16And this happens a lot. so I'm not going to tell people you know don't sleep with someone on the first date or any of those rules because every situation is different but just know that when you do move it that quickly to a sleepover in the beginning that it really can turn into something very casual and until you really know if you like someone until you actually set some boundaries and some standards you might continue to get taken advantage of. You might, you might not. You might meet your next date with another person might lead into something magical. You never know, you just never know. But I don't want you to be taken advantage of anymore.

16:02So with this guy, what I would do is completely withdraw. Not to play games. It's not to get him. It's not to punish him. It's to literally just say to yourself and be like, okay, this happened. It was a nice time. For whatever reason, it's not progressing into something else. It certainly doesn't feel good for me. I feel confused. I feel like now I'm chasing the guy. It doesn't feel good. So I'm going to go live my life now. And I'm going to demote him mentally from being up here, from being the prize to just some guy that I had a nice time with and, you know, and unfortunately it was one of those dating experiences where you thought, I thought that there would be some progression into something and it's not.

16:55And that's disappointing. And you have to kind of process your disappointment around that and learn from this experience and allow yourself to be pursued a little bit, allow yourself to, um, to be cherished, you know, um, you deserve someone who's going to want to see you want to spend time with you, want to invest in you. And after they've spent a night with you, if they're not doing that, then they just don't have the level of interest that's necessary. And I don't want you to feel badly about yourself, but I do want you to perhaps in the future, just based on how you ask the question to not go home with someone on their first date, to protect yourself, you know, and to understand the sort of dance of early dating and how protecting your physical and psychological and emotional boundaries are really important.

17:59So I hope this helps. This episode is sponsored by Jevity. Jevity is the first all-in-one precision health membership. Testing, clinician-built protocols, personalized supplements, and prescription therapeutics all in one plan. We simplify the path to a healthier you because your body is already sending you signals. The afternoon crashes, the plateau at the gym, the sleep issues that won't resolve, those are signals. Jevity helps you look under the hood and address them. The traditional healthcare system is designed to react, not to prevent. So you go once in a year, get a basic panel and here everything looks fine.

18:43But fine is a low bar. It means nothing is critically wrong right now. But that nothing could be building. 93 % of members see meaningful improvement from their first to second round of blood work. and members reduced waste of time on unnecessary supplement guessing by an average of 80 bucks a month. That's a lot. Listeners to the show will get an exclusive 20 % off purchase. All you have to go to is gogevity.com slash Jillian. So you want to go to G-O-G-E-V-I-T-I.com slash Jillian, promo code Jillian. Hi, so here's the situation and then I will state the question. I'm 34, he is 47. I have two children who are teenagers 15 and 12.

19:41He has two children from his first marriage that he's divorced from. Both kids have graduated. The second wife he is still married to but is telling me they are separated. We have been talking, sleeping together and going to dinners for the past five months, four or five months, and I still feel in limbo. And I've popped the question over this course of five months, about three to four times, you know, once pretty much every month to see where I stand with him. I've asked him and I've told him, I don't know where this is going. I am not sure where I stand with you. And his response is, don't you want to take things slow and just let them bloom?

20:28Have you ever done that before? And I understand his side. I get that. However, I feel like if we are going to take things slow and let them blossom into something more beautiful, then we should not be sleeping together and we should really reel it back and slow it down. And when I asked the question this last time at dinner, about two to three days ago, I still told him, I don't know where I stand with you. He looked at me kind of like I was crazy and said, we're sleeping together. We're not just friends. And which my response was, people do still sleep with their friends and you have not confirmed whether or not we are together.

21:13You are still married. You do not have an attorney involved in your divorce. You're trying to settle things on your own. And how am I supposed to know three years from now that you're actually going to get divorced? You could still be married and you're telling me to take things slow. Not that I'm trying to push him to do that. However, I do feel that I should be kept in a loop. And I also feel like I shouldn't have to keep asking this question where I stand with you. It's for someone his age and myself, I feel like there should be more directness and I shouldn't have to be consistently trying to pry an answer out, but perhaps I am wrong.

22:05no you're not wrong you're you are correct this is a 47 year old man we're not talking about people in their 20s and he should absolutely 100 in fact i have a producer sitting next to me who's a man and he's nodding his head and and agreeing that you are absolutely correct um so So look, it sounds to me like there's something, you know, he's separated but not divorced. He's dealing with it on his own. So there's a part of him that's not ready, it sounds like, you know, to fully commit. And I have no doubt that he cares about you and that he likes you. But it's five months. Him to say, well, don't you want to take this slowly and see what happens?

22:58and see how it blooms. I think it's really lame. I think it's incredibly lame. Five months, there has to be some sort of progression. Anything that doesn't grow dies. And why would you want to, as a mother of two, why would you want to waste five months of your life on someone where it it might not be going anywhere. I mean, unless you wanted something, unless you were content with the way things are and you're not, and no, you should not have to ask every month where you stand. Um, but I want you to, I, your communication has to change. And I'm going to get to that in a moment. I just want to first drive this point home.

23:49Are you just sleeping together and having dinners together? Are you doing anything else together? Have you met each other's kids? It just sounds to me like he has compartmentalized his life and he's got his second marriage that he's separated from and navigating a divorce without any lawyers on his own. I don't really and we don't really know what's going on there. You know, you're not like we don't really know the truth. I'm I'm presuming they don't live together anymore. I'm hoping so. and then he's got you and it's this lovely thing and he gets to control the pace and that's just not how it goes a relationship only had a connection or a relationship or whatever this is only has a chance to really blossom when both people are agreeing on the pace and right now Now, he wants it his way because I'm sure he's very overwhelmed.

24:50I mean, he's going through a divorce. That is no easy thing. And it's probably really intense for him. And the idea of like having that and then jumping into something else probably feels like too much for him. And I would understand that if it feels like too much for him. But what matters is you in this scenario. And that is not being in something where you are uncomfortable with the pace or feeling like it's not growing, but then having to capitulate because of someone else's circumstances. And so I would just say, like, if you're going to get involved with someone who's going through, who's separated and going through a divorce, sometimes what that means is that your connection with them can't progress at the pace and in the way that normally it would progress with someone else.

25:49and so you would have to decide you know what this is worth it for me I'm comfortable with this pace I know what I was getting myself into I understand that they're going through a divorce and so I'm comfortable with this but even then I would think you'd want to know like what is going on with that you know so this is the potential obstacle that comes with getting involved with someone who's separated and going through a divorce. Not every situation is the same, but this is a very common obstacle. I appreciate your concern is what I'm feeling that you don't want to push him, that you don't want to, um, yeah, you don't want to push him or be needy, but at the same time, you've got to be able to have a voice in any relationship and say exactly what's not working for you.

26:42And you can, you don't have to be demanding about it. You can do it in such a way where, um, you can say, look, I don't want to push you. I know you're going through something. I know you're going through a separation and divorce. And the last thing that I want to do is push you to do anything, um, or to move faster than what is comfortable for you. Because if that, if you do anything that doesn't feel right to you or if I push you, then that's only gonna lead to a bad place for the both of us. So that's the last thing that I wanna do. On the other hand, the fact that we are sleeping together, there's no labels, we're having dinners and it's been five months and there's no progression, doesn't work for me.

27:31I need things to grow. And if you are not in a place where you can do that, I understand because I knew exactly what I was getting into when we started dating. But this is this this pace doesn't work for me. And not knowing where I stand with you, not knowing really how you feel about me, not seeing any progress from month one to month five in terms of how we spend our time together and how close we are getting together. We are we are getting with each other. It's just not working for me. and that's how you communicate instead of what so many women do is you know they look to the man for leadership to decide where things are going and and i get that and i think that you know there is something very attractive about a man who who can take leadership and that does actually make, in this case, his female, his woman partner relax.

28:36But in this very delicate place of we're not quite in a relationship, but we're not not in a relationship, you got to have a voice and not say and not look to him anymore for leadership. You have to become the leader and the CEO of your own life and, and communicate. And I'm going to say it again, because this is so important and we're not taught this in school. It's not about being demanding. It's not about ultimatums. It's not about being mean. It's about being really direct and vulnerable. And I will say it again. You can tell him, I don't want to push you. I don't want you to be, I don't want you to have to show up for anything that you're not ready for, because that certainly is not a good idea for me.

29:28At the same time, letting things just kind of blossom naturally doesn't really work for me because we've been doing the exact same thing for five months and nothing has actually progressed. And that's not what I'm, what I want. And when you can be really direct, then you give him, It's like the cards are out on the table and then the ball is in his court and he can decide in that moment. Okay, you know what? Like I either have to step up because I don't want to lose this woman or as much as I don't want to lose this woman, I am not in this place to be able to give her what she needs. And you have to be brave and be willing to hear that from him.

30:16and never, ever, ever put yourself in a position where you are tiptoeing around someone else's problems because you don't want to lose them. It never works. You have to be brave and be willing to have the conversations that might rock the boat and might tip it not in your favor, but I am telling you it's better. It is better in the long run than to live in this kind of, I don't know, this discomfort, this frustration of not being an equal participant in a relationship and in terms of the progression of it and the pace that it takes. Anyway, I hope this helps. This episode is sponsored by Masterclass.

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32:29That's 15 % off at masterclass.com slash JOL. Head to masterclass.com slash JOL to see the latest offer. How do I recognize early in a relationship whether someone is truly ready for real intimacy or whether they just want the concept of a relationship without the depth? And in a similar way, how do I recognize or how do I, how can I see if someone has, yeah, the emotional maturity already to actually have an intimate or is actually ready for an intimate relationship? Okay, so some of the signs that someone has the emotional availability and maturity to be in a real relationship that requires real depth, as you said, and emotional intimacy, which is what I believe you were referring to, is this.

33:37um well for one it's someone who is so a lot of people who sort of want the benefits of a relationship without any of the responsibility of a relationship everything is about it has to be easy and fun all the time it can't be inconvenient um there can't be any sacrifices made. It has to be all on their timeline and all when it works for them. But a relationship is about giving. It's really not about taking. I mean, yes, it's about receiving, and there's a fair amount of people who are watching this or listening to this right now who have a hard time receiving, but it's really about someone who wants to actually meet needs as much as they actually want to have their needs met.

34:42And so you know when someone is ready for a relationship and ready for that kind of depth, when they actually want to invest in you and they want to invest in the relationship And what that looks like is when there's like a little snafu or a little argument, they don't run away. They are, let's figure this out. When there's a, when you need something and it's not a hundred percent convenient for them, you know, most times, more times than not, they're going to prioritize the relationship. right? I mean, the thing is, I don't believe a relationship should demand these huge sacrifices, but there's a difference between being single and being in a relationship, right?

35:35We all know that. And when we're single, we get basically, if we don't have kids, we get to do whatever we want when we want to do it. But when we're in a relationship, we actually have to consider the thoughts, feelings, life, heart of another person. And when we are really committed, we want to do that. Yeah, the emotional maturity is I am prioritizing us and my life is not just about me anymore. It includes we. and what defines emotional immaturity in a relationship at the very like core of it is selfishness. Me, myself, and I, all that matters are my needs. All that matters is, you know, my day.

36:35All that matters is what I want to do. All that matters is that I'm having a good time. and relationships are sometimes inconvenient and they do take work now I don't think a relationship should be ongoing laborious work if it is it's probably the wrong relationship but it still takes some work it's like how do we integrate our lives so that we are prioritizing the we and so that's how you know and in the very early stages it's kind of hard to know because it's when you see each other, it's really when you see each other stressed out for the first time or when you have your first argument and how willing the person is able to kind of work through that with you.

37:22It's also, um, you know, when someone's really in it and really ready for it, you may have heard of this, but when you break down intimacy, the word intimacy, you, You have in, to, me, see. So there's more sharing of each other. There's more vulnerability. And the more that you open up, the more the other person is like, I want to know even more. People who are truly emotionally available to you, like they want to be with you and they want to be in a relationship and they have the capacity to be in a relationship. They want to get in here. They want to get into the heart. It's also about making space for another person in your life.

38:13I've met with a lot of people where it's like, like I said, they have so much control over their lives. Everything is so regimented. Everything is so controlled exactly how they like it. And then they start seeing someone and it's like, oh, the person wants to come over. They have to change the way they operate in their day. And they're like, yeah, I like this person, but I don't want to change anything. It's like, well, then you're not ready for a relationship. Because a relationship is about making those changes, but they shouldn't feel like these massive sacrifices. They should feel like I'm making these changes for something great and for something that I want.

38:53Because none of us can have everything that we want all the time. We have to make room for the things that we want in our life. So I hope that helps. Jillian on Love is a Q-Code production, executive produced by David Henning and Steve Wilson, produced and edited by Travis Howe. Music by Will Tendi. Coca-Cola. For the big. For the small. The short. And the tall. Peacemakers. Risk takers. For the optimists. Pessimists. For long distance love. For introverts. And extroverts. The thinkers and the doers. For old friends and new. Coca-Cola. For everyone. Pick up some Coca-Cola at a store near you.

40:15Cross.

From the publisher

Have you ever found yourself making excuses for someone's mixed signals? In this episode, Jillian answers three listener questions that all point to the same truth: healthy relationships don't leave you wondering where you stand. She explains why chasing someone who isn't investing in you only leads to confusion, why consistency matters more than chemistry, and how to communicate your needs without sacrificing your standards.

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