is it time to move on? advice session

20 Jul 2025 · 50 min · 11 chapters

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In short

Relationship advice on when to move on, handling “missed out” feelings, whether breaks are healthy, boredom in long-term relationships, and how to decide about age-gap dating and “right person, wrong time.”

Guests

No guests. The host gives advice directly to multiple listener questions.

Key claims

Regret isn’t healthy for “what if” relationship choices; focus on now and fulfillment. “Breaks” are often messy and can enable cheating; healthy space is okay only with clear mutual agreement. Boredom after the honeymoon phase is usually normal unless connection is shallow. After 1–5 years, you should discuss shared goals; inability to communicate is a red flag. Age gaps under 25 can create power imbalance due to differing maturity; respect a partner’s discomfort and don’t pause your life waiting for “right time.”

Notable examples

Freshman-to-senior college partner “missed out” worry; four-year boredom; five-year relationship “not going anywhere”; dating a boy best friend; 19 dating 26; 24 considering a 9-year-older man.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Recognizing When to Move On

0:45 to 2:24

Emma discusses the challenges of realizing when to move on from a relationship.

“in love and I made excuses for them and I had made up my mind that this was my soulmate and I wasn't going to give up and so you know I would almost turn a blind eye to stuff that they were doing that was terrible.”

Advice on Feeling Like You've Missed Out

3:12 to 7:46

Emma provides advice on a listener's feelings of missing out on casual dating during college.

“Somebody said, I've been with my partner since freshman year in college.”

Taking Breaks vs. Breaking Up

7:46 to 14:00

Emma shares her views on whether taking a break in a relationship is healthy or toxic.

“Because at the end of the day, we have to live life for us.”

Navigating Boredom in Long-Term Relationships

14:00 to 21:57

Explore the dynamics of boredom in long-term relationships and ways to rekindle excitement.

“And then the other person who's like, I love you so much, I'll do anything for you.”

Addressing Relationship Stagnation

22:29 to 28:00

Advice on how to address feelings of stagnation after years in a relationship.

“Somebody said, I feel like my five-year relationship is not going anywhere and I'm having a mentee B.”

Navigating Relationship Transitions

28:00 to 29:10

Emma discusses the complexities of transitioning from friendship to a romantic relationship.

“But if both of you are dedicated to figuring out this transition, which I can imagine would be really uncomfortable if you were really close for a really long time.”

The Foundation of Friendship in Dating

29:10 to 30:46

Emma shares her experiences emphasizing the importance of friendship in romantic relationships.

“the fact than it is to figure out the sexual piece after the fact.”

Right Person, Wrong Time?

30:46 to 33:58

Emma explores the concept of 'right person, wrong time' in relationships and the need to move on.

“Somebody said, do you believe in right person, wrong time?”

Understanding Age Gaps in Relationships

33:58 to 37:43

Emma discusses the implications of age differences in relationships, highlighting maturity levels.

“Not impossible, but don't wait up for it.”

When Age Gaps Matter

37:43 to 42:00

Emma elaborates on how age gaps affect relationships and the importance of maturity at different ages.

“You're going to look at him like he's this, you know, oh my God, God, he's so much older and so much cooler.”
Show all 11 chapters

Navigating Age Gaps in Relationships

42:00 to 46:38

Emma discusses the complexities and considerations of dating someone with a significant age difference.

“The older you are, the more irrelevant the age gap becomes.”
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Transcript

Automatic transcript. May contain errors.

0:00Welcome back to Advice Session, a series here on Anything Goes where you send in your current dilemmas or anything, and I mean anything, you want advice on. And then I give you my unprofessional advice. And today's topic is one that we know and we love, relationships. But more specifically, when it's time to move on from a relationship, which is an incredibly challenging dilemma because it's really hard to think clearly in a relationship. when you're in love or you think you're in love it's really hard to think straight at least that's been my experience like it's actually mortifying to me when I look back at all of my past relationships how much shit I let slide because I was in love or I thought I was in love and I made excuses for them and I had made up my mind that

0:52Emma Chamberlain:this was my soulmate and I wasn't going to give up and so you know I would almost turn a blind eye to stuff that they were doing that was terrible. Like, it's so hard to honestly analyze a relationship when you're in it. It's so challenging. But today I'm going to be giving advice on it. Even though I can't say for sure it's something that I won't do again, but I'd like to believe that I'm a realist in relationships now. Like I've gone into enough relationships being like, this is my soulmate. They can do no wrong. We're getting married. I can't wait for our wedding. I'm going to wear a beautiful dress, long sleeve, but kind of off the shoulder.

1:33Emma Chamberlain:It's going to have no sparkles because I don't like that stuff. Maybe a little bit of lace. I'm gonna have a super long veil. Maybe we'll get married in like, in like Cape Cod or something, or maybe like, maybe something local, like California vibes. Like I've done that enough. And then because I've become so dedicated to the idea of like, this is my person that then I've made excuses for them throughout the entire relationship. And then at the end, become mortified that I did that. I've done that enough times now in my life that I really am crossing my fingers that it's not going to happen again.

2:05But I can't make any promises. But I'm going to give advice on it anyway. And I'm going to be listening to myself while I give this advice. because sometimes I need to hear my own advice. Anywho, let's dig in, shall we? I briefly interrupt this episode to let you know that this episode of Anything Goes is presented by Walmart. Summer's back, baby, which means a whole new wardrobe. Thankfully, you can find trends that speak to you for less at Walmart. You know, for me, summer is about simplicity and comfort because warm weather is pleasant, but only if you dress properly for it. So I'm trying to wear breathable but cute clothing all summer long.

2:52From casual hangs to vacation, Walmart's the place to find all your summer pieces. Think chic eyelet styles, breezy dresses, it girl shoes, vibrant colors, and more. Shop the hottest summer trends and new drops at walmart.com slash trends. That's walmart.com slash trends. Now back to the episode. Somebody said, I've been with my partner since freshman year in college. And now that I'm a senior, I feel like I might've missed out. What do I do? Well, to start, I truly believe in no regrets in life. I mean, listen, if you do something really, really, really fucking bad and evil. Maybe then regret is a necessary healthy feeling.

3:37But when it comes to something like this, I don't think regret is necessary or healthy. That's my opinion. Because you can't change it. You can't go back in time and not be with this person. It happened. And you can't rewrite history. So it's healthier to just accept that that is the past. It happened. You can't go back. and look at it fondly. Remember it fondly instead. There's a reason why you chose to be with your partner all throughout college. Like if in the moment it was miserable and you hated it, chances are you would have ended it and you didn't. And, you know, it doesn't sound like your partner treated you badly.

4:20You know, I feel like that would have been mentioned if that was the case. It sounds like you're more worried about missing out on dating casually, hooking up with people. It doesn't sound like your partner is a bad partner. It sounds like you're actually still with this person. Here's what I have to say to that. The feeling of, oh, what if I missed out? Number one, the grass is always greener. Okay. Not having a partner in college, hooking up with people randomly, dating casually, not being sort of tied down, if you will, in a relationship is probably a fun experience too. If you had done that, there's a chance that that would have been enjoyable.

4:58But I don't think one would be more enjoyable than the other, just different. And again, like the grass is always greener, right? There are people who spent their entire college experience doing the opposite of what you did, you know, hooking up with people, dating casually, who perhaps regret not dating somebody that they had feelings for because they wanted to be free and hook up with people and whatever. Like, there's somebody out there wishing they had the experience that you had. The grass is always greener. And again, you can't change it. So it's better to just accept it as the past and focus on right now.

5:40Focus on what's going on right now. But you're still faced with a dilemma, right? Once you let go of that feeling of regret and what could have been, you're still faced with the dilemma of what to do right now. Because if you're feeling like, oh, I think I might've missed out. Like, I really want to know what it feels like to date casually. And, you know, if you're yearning for that, I think part of that is normal in a relationship every once in a while to be like, ooh, what would it be like to be single again? Like, I think that's a universal experience. And I think that's often a phase that people go through in relationships.

6:14But if that's overwhelming to you and you're like, I don't know that I want to be with this person for the rest of my life. I think it's more important to me that I go out there and I explore. That's okay too, you know? And it's not too late to be single and to enjoy that experience. You can do that at any point in your life. Just because college is over doesn't mean that you can't go do that now. That's a limiting belief that's false. Like, yeah, you can't go back in time and go to college and do it again, but you have your whole life ahead of you. But I also think another thing to consider is why do you feel like you missed out?

6:55Do you feel like you missed out because you didn't have the same college experience as your friends? Do you feel like you missed out because societally people sort of romanticize the experience of being single and dating around in college? Like, where is this thought coming from? Is this thought coming from you genuinely feeling like, oh, I think I missed out? Or is it coming from the outside? because if it's coming from the outside, it might be helpful to look inward instead and figure out how you feel about it. But if it's something that is coming from the inside, it's coming from you, then I think it's something to take more seriously and figure out what your next step is, which is tough, you know what I mean?

7:38But I think the guiding light when it comes to making that decision should be, what is going to bring me more fulfillment in my life? is it continuing to build this relationship with this person so that ultimately one day we can have a family or one day we can move to New York City together or whatever your dreams are for this relationship or would it be more fulfilling for you to have an experience in you know your young adulthood where you're single and you can hook up with whoever you want and you date around and you see what's out there only you can figure that out but you just have to make sure that these feelings and these doubts and these concerns are coming from you and are not coming from any outside sources because it can be very easy to make the wrong decision if you're not listening to yourself, if you're, you know, if you're being influenced by other people.

8:33Because at the end of the day, we have to live life for us. And I've had moments in my life where I felt like, oh, did I miss out on being single and being sort of promiscuous? I don't know if that's the right word. I mean, I guess promiscuous. Did I miss out on, you know, dating casually and hooking up with people when I was younger? Because I've been in relationships pretty consistently since I started dating at like age 17. Like, what did I miss out on? I've had feelings like that. But whenever I look inward, I realize, honestly, I don't think those doubts are coming from me. I think those doubts are coming from society and people around me.

9:14I made the decisions I made because that's what felt right. And that's what felt me, you know. And those were the decisions that felt like they were the most fulfilling in the moment. And when I have dated casually and been single and like, you know, just hooked up with random people, I haven't liked that. You know, I haven't enjoyed that experience. So I wish you luck. Somebody said, how do I know if I should just take time apart from someone or break up for good? Is it ever okay to just take a break without fully breaking up? Or is that toxic? Okay, well, I have my own personal opinion on this.

9:56However, I don't necessarily think everybody needs to abide by my opinion. Does that make sense? Like, this is my opinion. This is my sort of philosophy and my sort of boundary in my own personal life when I'm dating people. But I don't necessarily think it's the right answer for everyone. It's more catered to me as an individual. I personally am an all or nothing girl. Like you're either dating me and we are together and we're going to figure it the fuck out together or we are broken up and that's it. No halfsies. No like, oh, we're going to go on a break for a month and like we're not really dating.

10:32Like we can see other people, but then at the end of the month, we'll get back together and we'll be back together. No, I'm sorry. Fuck that. I can't do that psychologically. That is too messy for me because if I find out that on that break, my partner or ex-partner for the moment, like hooked up with somebody, uh-uh, too messy for me. My thing is, if you want to go get with somebody else or you don't want to be around me for like a few months, why are we together? Like the whole point of a relationship is it's a partnership. We're going to get through this shit together. You can fully take a break while in a relationship.

11:10It is very healthy. to take time apart while dating. If it's possible for one member of the relationship to like go on a trip for two weeks and the other stay home because, you know, you two need space, but there's an agreement, a mutual agreement, like we're still dating, we're still together, we're going to figure this out, but we just need space. That's so healthy. There's nothing wrong with that. And in a lot of ways, that is a break. But I feel like the break that we all know is like, oh, you know, we're not dating right now. We're taking a break from dating for like

11:46Emma Chamberlain:one month or for, you know, two months and then we'll get back together at the end. But while we're on the break, we're not really dating anymore. What is that? Listen, I really don't believe in it. I think it's fucking messy. And I think you're better off just breaking up, it's clear that one of you or both of you can't fully commit to what a monogamous relationship is, which is committing to one another through thick and thin. Relationships are so fucking challenging, especially the deeper that they are, the more vulnerable that they are, the more meaningful that they are, the more challenging that they are, you know?

12:25And that's what makes them potentially so rewarding, but they're rewarding if you get through the tough times together, you figure out a solution together under the roof of your relationship. Does that make sense? But if somebody is like, oh, I think I just need a month off. It's like, that's not how it works. That sort of, in my opinion, I think that that is like having your cake and eating it too. Like you get to have the security of like, oh, this person is waiting for me, but I get to go like hook up with other people. That erases what makes relationships, monogamous relationships in particular, so powerful.

13:03They're so powerful because it's a partnership where you're committed to one another and that's challenging. That's a challenging thing to do. But through the challenge and through overcoming the challenge together, you become closer as a result, thus forming a very special relationship and bond that can be really wonderful and fulfilling for people. And an ongoing growth experience for both members involved. But if you take a break and you get to like kind of cheat for a little bit, it just doesn't feel right to me. And so I think it's all or nothing. However, if you can have a conversation with your partner and you both come to the conclusion that you both are comfortable 100 % with going on a break where you both can do whatever you want and both of you feel okay with that, who am I to judge?

13:51you know what I mean? But I would argue most people would have a really hard time with this. And it's usually one person in the relationship who can't fully commit. And then the other person who's like, I love you so much, I'll do anything for you. And they're settling and they're allowing bad behavior just to end up breaking up a few months later when you try to rekindle, but then somebody, you know, the one who's struggling to commit ended up hooking up with somebody. And then the one who's super loyal obviously didn't. And then they get heartbroken. it's messy. I say no to the break. But again, if you can figure out a way to do it, I mean, don't let me stop you.

14:31Somebody said, I've been in a relationship for four years and I'm kind of bored. How can I know if it's just a phase? Is this normal? I have good news and bad news. In my opinion, this is just a phase. This is the reality of a long-term relationship. and it makes sense, right? Like it makes logical sense. The beginning of a relationship is really exciting and really exhilarating because you have so much to discover about the other person. You don't know what their genitals look like and then you find out one day and it's like, oh my God, that's so exciting. Like you finally get to see like taint and it's like, oh my God, I can't believe I got to see that.

15:11And then the next day you find out about a new little cute freckle that's on the back of their neck that you've never seen before. And then the next day you see what it's like when they cry. And then the next day, they open up to you about something vulnerable. And then the next day, you figure out their sense of humor. And then the next day, do you see what I'm saying? It's like the beginning of a relationship is so exciting because you're constantly discovering something new. But at a certain point in a relationship, you've seen a lot. I don't think you've ever fully seen everything. I think there's always more to discover about another person because you're not in the other person's brain.

15:45And therefore, you'll never truly know what it's like to be them. You'll never truly know what goes on inside of their brain. There's always more to discover. But the exciting discoveries, or even really just the discoveries at all, they're less frequent, they're less often. You know, you get to a point where you're so familiar with your partner that it's like, yeah, it's not exciting. It's not exhilarating.

16:08Emma Chamberlain:But you know what it is? It's comfortable. it's familiar and a lot of times it's really healthy like it might not be exciting and exhilarating it might not be super hot and sexy and like oh my god I'm like seeing their body in a new like I've only seen their body a few times now I get to see it again and it's still exciting like naturally all of this is going to wear off but when that all wears off you're left with something potentially really wonderful just in a new way. And the truth is, is that I think a lot of people throw away beautiful, healthy relationships because they're like, wait, where did all the excitement go?

16:53Like, where did all of the hot, steamy romance go? And they throw away a really healthy, beautiful partnership because they want that excitement of the beginning of a relationship, but that will never exist forever. You know what I'm saying? Unless there's a weird power imbalance, which is unhealthy. Like excitement can continue if you're dating somebody who's super avoidant, who you feel like you have to win over every day. But who wants that? That's a toxic existence. I've done it. It's not fun. In my opinion, this is only a serious issue if you feel that the boredom is rooted in a lack of depth in connection, thus leading to neither of

17:35Emma Chamberlain:you growing or having riveting conversation or, I don't know, really like connecting on anything meaningful. If that's why you're bored, because your relationship is surface level and you're not kind of nudging each other to grow and be better and think differently, then yeah, that might be a problem, you know, and that can happen. Like there is a chance that you're feeling this way, not because it's normal, but because you don't have a deep connection with your partner. You've been able to sort of skate by maybe by having similar hobbies or, you know, maybe having like a really extreme sexual chemistry, but your relationship is actually not really rooted in any sort of meaningful, deep connection.

18:23I think the questions to ask yourself is, do you know your partner? Do you feel like you know your partner like the back of your hand?

18:29Emma Chamberlain:Is there anything that you're curious about? Like, are you like, oh, I actually don't really. It's shocking. You can find yourself four years into a relationship and realize I don't really know that much about this person. And that has happened to me where I've woken up one day in a relationship and been like, we don't even know each other that well. Like maybe we have the same sense of humor. So maybe we laugh together, this or that, but like, we actually don't know each other. And if that's the case, and that's why you're bored. I mean, either you make a plan to figure out how to have a deep connection with that person, or maybe that's the end of it.

19:05And maybe it isn't just

19:06Emma Chamberlain:a phase and you're actually catching on to something that's a real problem in the relationship. But I think more often than not, what you're experiencing is genuinely just a phase. And I do think that there are ways to spice it up. Like, listen, if you want to spice it up, maybe plan a monthly date night. Maybe plan a trip together. Maybe plan a new like hobby that you guys can try together. Maybe buy like lingerie. Listen, you'll never catch me buying lingerie as much as maybe people wish I would. Okay. But I like, that's to me cringe, which is actually something I should probably talk to a therapist about the fact that I feel like the thought of me and lingerie is cringe.

19:42Emma Chamberlain:Genuinely, there's something wrong probably there. Again, I should probably talk to a therapist about that. But, you know, buy a fucking sexy Santa costume. Buy a sexy nurse costume. Fuck it. Do nurse role play. You know what I'm saying? You get what I'm saying here. Like, make an effort to spice it up if you feel inspired. If you don't, it's probably just a phase that will pass. But I really do encourage you and people in long-term healthy relationships to find the beauty in the peace of a long-term relationship. there's so much value there and it is a bit harder to it's less exciting it's less obvious it's sort of a beauty that whispers for your attention rather than screams for your attention like in the beginning of a relationship it's so exciting it's screaming for your attention but the longer that you're together the beauty is much more subtle you know but it's also much more real and it's something that can actually last.

20:40Emma Chamberlain:Nothing that's that loud can last. I don't think it's too, do you know what I mean? Enjoy the peace and the freedom that comes with a long-term relationship. When you're loved by somebody and you have a beautiful partnership and that's something that is a priority for you in your life, that can give you so much freedom to go and focus on your career, to go and, you know, focus on hobbies, to go like do this or that. And you have this person waiting for you at the end of the day at home who loves you and supports you. And you don't have to be playing the dating game anymore if being in a relationship is something that you care about.

21:14Emma Chamberlain:And that's a priority for you in your life, which again, isn't for everyone, but it sounds like it is for you because you've been in one for four years. There's so much freedom. You get to almost return to your life when you're in a healthy relationship because dating is like a full-time hobby. It's exciting, but it takes up a lot of time and energy and it can get in the way of other things, which is okay for a period of time in life. But at a certain point, I think a lot of us want to go back to our lives, you know, get back to work, work on our hobbies, hang out with our fucking family. I don't know, but there's something beautiful about the freedom that you can have in a long-term healthy and perhaps boring at times relationship.

21:57I briefly interrupt this episode to let you know that this episode is brought to you by hotels.com. Okay, I'm going to let you in on a little secret. Hotels.com could help you level up your vacation. So if you sign up for free, I might add, you save up to 20 % on select hotels. Yep, up to 20%. That's actual real money back in your pocket, which means yes to massages, yes to room service, yes to those little extras that make a trip feel extra special. head to hotels.com to book now. Now back to the episode. Somebody said, I feel like my five-year relationship is not going anywhere and I'm having a mentee B.

22:36What do I do? This is, you know, kind of a similar dilemma to the last one, but a little bit different. After five years, I think it's appropriate to sit your partner down and be like, hey, what are we doing? Like, do we have the same ideas for the future? You know, do we have the same goals for the future? do you want to get married? Do you want to have kids? Do you want to move to Los Angeles? Do you want to move to Texas? Do you want to move to France? Do you want to have three kids? Do you want to have one? Do you want to have zero? Do you want to break up? Like, what do you want to do? Because if you're somebody who, you know, has a certain sort of set of goals for your future, when it comes to your family, if you want to have kids, if you don't want to have kids,

23:21Emma Chamberlain:If you want to move here, if you want to open a coffee shop, like after five years, it's more than appropriate to figure out if you're on the same page. In fact, I think it's appropriate to do that even sooner. You know, I think after a year or two, it's appropriate. Don't sit around and guess what your partner's thinking. Sit them down and ask. And the truth is, if you don't feel comfortable sitting them down and asking, chances are they're not the one for you. You don't have a healthy relationship with an open dialogue with each other. If you can't sit your partner down and ask, are we on the same fucking page?

23:55Emma Chamberlain:Red flag major. You're not comfortable with each other. You haven't built a true partnership yet. Not saying you couldn't, but that's an issue in itself. If you're sitting around wondering things after five years, that to me is actually a red flag. Because again, after five years, it's like, you shouldn't have any questions about your partner. You should know them really well. You've had a lot of time. So if you still have questions, there's a chance it's because you're not fully comfortable with each other. You're not fully being vulnerable with each other. You're not fully open with each other.

24:30Emma Chamberlain:You're in each other's lives, but you're not truly committed to a partnership. Because committing to a partnership is, it's a whole thing. You know what I mean? Like in order to truly get the most out of a romantic relationship, you have to be sexually vulnerable. You have to be emotionally vulnerable. You have to be honest. You have to be truthful. You have to be kind. There's so much to it to make it truly a partnership where both members are growing and it's actually a beneficial thing for everyone involved, you know? And if you can't sit your partner down and have this conversation, then that's clearly not happening.

25:10so that needs to be figured out first but there's a chance that you might sit your partner down and

Read the full transcript

25:14Emma Chamberlain:have this conversation which can potentially be uncomfortable and discover that you both actually are even more aligned than you ever even knew that's the best case scenario and then what well I think then your focus needs to be how do we get to a point where conversations like this are comfortable and easy and that we don't even need to really have conversations like this because we already know what do we need to do in our relationship to get to that point how can we be more vulnerable with one another. How can we communicate with one another better on an ongoing basis so that we always feel synced or, you know, as often as possible, we can feel synced on the same page.

25:50Emma Chamberlain:And worst case scenario, you know, it doesn't work out. And guess what? That's not five years wasted. I know that that's what you're thinking. You're like, I'm having a mentee B because I have just spent five years with this person and now I'm feeling like it's not going anywhere. And I think it's time to move on. But if I move on, I just wasted five years of my life. Like what now? No, you didn't. You did not waste five years of your life. Every relationship that you that you experience in your life will teach you things that will make you wiser and even better in your next relationship. There's like no such thing as wasting your time I'm in a relationship, I don't think.

26:32Emma Chamberlain:Again, I'm really against regretting things that you can't change that aren't wrong, you know? Like, it's not wrong to be with the wrong person for five years. That's not wrong. It's wrong to hurt somebody really badly. In that case, regret it. You know what I mean? But it's not, I don't think it's necessary to regret that. For whatever reason, the universe wanted you to be in this relationship for five years so that for whoever you're going to be with next, you'd be ready. That's how I like to look at it. And I don't mean to get spiritual with my advice, but sometimes the spirit speaks. Can't help it.

27:05Can't help it. Somebody said, I started dating my boy best friend of two years, and it is kind of weird to navigate the transition. Will it get better?

27:14Emma Chamberlain:To be honest, I think anything can get better in a relationship between two people who have a genuine friendship and genuinely love each other and care for each other. I think anything can be solved between two people who have a relationship like that through honest communication and mutual dedication. And that rhymed. So that's kind of awesome. But I really think that if both of you can talk through it together, honestly, and genuinely, and I think if both of you are truly dedicated to figuring it out, anything is possible. I really believe that. it's when one person stops communicating or when both of you stop communicating.

27:57Emma Chamberlain:It's when one of you becomes less dedicated or both of you become less dedicated. That's when it's harder to say. Actually, it's not even harder to say. That's when things won't work out. But if both of you are dedicated to figuring out this transition, which I can imagine would be really uncomfortable if you were really close for a really long time. And then now all of a sudden it's like, wait a minute, like your pants are off. It's weird. It's weird. It would be weird. I've actually never really done that. To be honest, I, it's funny because I'm the first one to preach like relationships built on friendship first are set up for success far more than relationships that start with lust.

28:36And then, you know, because a relationship at the end of the day is a friendship

28:41Emma Chamberlain:where there's a sexual element, but it's, it needs to be a friendship arguably first, you know, because you're not having sex all the time. You're having sex like 5 % of the time. And then the other 95 % of the time, you're friends. That's really what you are. You're friends who maybe every once in a while, like touch the butthole, like when the other one's walking up the stairs, like that's, that is dating, but you're really just friends. So if you don't have a solid friendship, good luck. And it's much harder to figure out the friendship piece after the fact than it is to figure out the sexual piece after the fact.

29:12I feel like the sexual piece, Sometimes you're just not compatible. So be it. But I think that's something that can usually be figured out or experimented with much easier than the friendship element.

29:26Emma Chamberlain:So I really believe you guys can figure this out. Like, I believe it with my whole heart. You know, the closest thing I ever had in dating, when I look back at my past relationships, the relationship that I think has been overall the most successful from a problem solving standpoint, like the person that I've dated that I've been able to problem solve the best with overall was the person that I was friends with for the longest first. Does that make sense? and I mean we weren't friends for very long and there was always sort of this undertone of like dating but we didn't have any sort of sexual interaction with one another for like a month and a half like we just talked on the phone for like a month and a half and then met in person and you know and then we're dating but you get what I'm saying and we really got to know each other and build a foundation again it's not like fully being like besties first but it was the closest thing I've ever had to that.

30:24But I will say that particular relationship, the problem solving was the most successful.

30:30Emma Chamberlain:And so based on personal experience, I think you fucking got this because you have that foundation of friendship. That might be what's kind of getting in the way and making things weird right now, but it's also the thing that's going to help make it possible to solve it together. Okay. Somebody said, do you believe in right person, wrong time? I fell for this boy, but I just got accepted into college and he already has a job and a car and his life figured out. We're in different phases of life, but it seems we can't leave each other alone. Part of me believes once I start university and get a job like a real adult, we'll meet again and work better together.

31:04Of all the boys I've ever talked to, he's the one I feel is the most sincere and we fit so well together. But he says he can't date me because of the age gap.

31:12Emma Chamberlain:I'm 19 and he's 26. Okay, before we get into the age gap, because I do have a lot to say about that. I have a lot to say about it. Not necessarily say, well, I'll get it. Let's wait. Let's put a pin in the actual age gap and first touch on the right person, wrong time thing. Okay. Because I actually do believe in right person, wrong time. I think that that's absolutely possible. I also think that you can't wait around for it. Like you can't put your life on pause, your dating life on pause, your love life on pause, because you think that you've met the right person at the wrong time. You know, that is the worst thing you can possibly do It might be true that this is the right person and that this is the wrong time However, you have to proceed with your life as though that's not true Because the only way to find out if it is true is if it comes back to you and I really do believe not to get spiritual again But like if it's meant to be it will come back to you.

32:08Emma Chamberlain:I really do believe that's true And i've heard so many stories of people who you know who did find each other at the wrong time and ended up coming back together years and years later after dating other people. I hear that story all the time. And I really do believe in it, but I think you cannot put a pause in your love life because you might be wrong. It might not be right person, wrong time. It might just be wrong person, but you really like them. That's a harsh reality, but it might be the case. And in order to figure that out, you need to go out there and try other things and see if something else works.

32:44Emma Chamberlain:And there's a really solid chance that something else might work better. And you might realize, oh, it wasn't right person, wrong time. It was wrong person, wrong time, wrong everything. But I just kind of like them. Like I thought they were cool and they were nice. And you know what? I wish them well, but they actually weren't right for me. Like there's a really solid chance that that will happen. So it's tough because as much as it might be true, there's no way to know for sure. and you cannot like not date other people because you're waiting for them. That's the worst that you'll, listen, I don't like believing in regrets or wasting your life, but that's a way to waste your life.

33:23Emma Chamberlain:And it's so painful to move on when you think you've met the right person and it's the wrong time. But I can tell you from experience, every breakup that I've been through, I've been like, it's the right person in the wrong time. Just to then realize like a year later, two years later, five years later, ooh, it wasn't, it wasn't. It's crazy how convinced we can become that like, oh, this person is it, this person is the one just to be completely fucking blatantly wrong about it and to find that out years later. So that's how I feel about the right person, wrong time. Not impossible, but don't wait up for it.

34:01Emma Chamberlain:Now let's discuss the age gap, okay, right? If he does not feel comfortable with the age gap, respect that. Okay. I actually find it really admirable that he feels uncomfortable with the age gap because it's a sign that he feels that there's a power imbalance. He feels like I'm more mature than her. I have more life experience than her. You know, it's almost like he could perhaps manipulate you in ways that you wouldn't even understand because you're 19 and he's 26. so much happens between age 19 and 26 it's like so much happens between age 20 and 24 okay I'm 24 now right when I look back at myself at 20 I think that is a child I would feel uncomfortable dating a 20 year old to be honest and that's not even that large of an age gap I mean four years in your 20s a lot changes but it's not like a super controversial age gap you know like 20 to 24 I would still personally feel uncomfortable dating a 20 year old because I was so different at age 20.

35:12Emma Chamberlain:So different. And I was so much less mature. I just every year that goes by, I feel like in your 20s specifically, every year that goes by, it's like 10 years. And so the fact that he's feeling that is actually really admirable. And I think you should respect it. like that's respectable. And you might think that you're mature enough to be with him. You really might feel that way. But I can almost guarantee you, you're more immature than you think you are. And I'm not saying that to be mean. Because when I was 19, I thought I could date a 30 year old. I really believe that I was like, I'm an adult.

35:49Emma Chamberlain:I'm 19. No, 19 going on 30. Like, send me the next 30 year old. That's hot. I'll date him because I can fucking do this. in retrospect, that is idiotic of me. But I was 19, you know, but I felt big and adult and like, you know, but also I think dating, you know, in your early 20s, because you're 19, you're almost 20. It's complicated because it's when maturity really starts to show. Like, I don't know. I look back at when I was 19, 20 and I was attracted to guys that were older than me. And I dated guys that were older than me, you know, by not by seven years, but, you know, by a little bit less than that, not by much less, because I felt the same way you did.

36:36I felt like this is the most sincere,

36:40Emma Chamberlain:nice, mature guy I've ever spoken to. Like I, this is magic. The truth of the matter is, it's just because perhaps you've matured a little bit quicker than the boys your age. You know what I mean? And that's very common. And there's something really refreshing about being with a guy who's like mature and has their shit together and is respectful. And it's like, and younger men sometimes are not as good at that. Takes them a few more years. You know what I'm saying? I get it. I get where you're coming from. And I don't want to undermine your feelings towards this man because he might be truly your soulmate, but this age gap is wide.

37:17Emma Chamberlain:It is. It's wide. And I think you're feeling the way you feel about him, not because he's even necessarily that special. Again, I, I'm like, I hesitate to say that because he might genuinely be magic and you two together might be magic. But I think what you're experiencing is just a mature man. And yes, there is something really wonderful about that. But I think the age gap for him is too wide. He feels there's a power imbalance and he's probably frightened that he's going to, you know, that you're not going to be able to hold him accountable because you don't have enough life experience. You're going to look at him like he's this, you know, oh my God, God, he's so much older and so much cooler.

37:54Emma Chamberlain:And like, you're going to idolize him and put him on a pedestal naturally. And that's not good for him because he needs somebody with enough maturity and with enough like life experience to be like, uh-uh, you can't behave like that. Uh-uh. You know, do you get what I'm saying? I really find it admirable that he's uncomfortable. It is a really, it is a wide age gap, but I think it's only a really wide age gap because you're 19 and he's 26. Okay. If you were to tack 20 years onto this, right, you're 39. He's, I don't want to do the math. You guys, he's like, what? 39 you're in your, and he's in his forties.

38:36Emma Chamberlain:Then you have a different situation. At that point, maturity is a completely different conversation. You're prefrontal lobe has been developed for a long time, both people, you know what I'm saying? And everything sort of evens out. I think once you get past the age of around 25, everybody's brain is pretty like set in stone. So age gaps don't matter as much. But before that, there's so much brain growth that happens every single year that his prefrontal cortex is fully developed and yours is not. You're not above science. You're not above biology. That is reality. so there will be issues there there will be a power there's there's a good chance that there'll be there'll be a power imbalance is there a chance that there wouldn't be sure but there's a strong chance that that could happen and I don't know I think there is a chance that it's right person wrong time you guys might you know maybe when you're 25 and he's like what 32 maybe then you rekindle because at that point, the age gap doesn't matter as much.

39:42Emma Chamberlain:But right now the age gap is very, it's wider than it would be post prefrontal cortex development. But again, I don't want to judge or like it's everyone's so different and everybody matures at such a different speed. And there's so many variables and everybody's so fucking, I can't even like, I can't fully comment on your situation and tell you what to do and tell you if there's a power imbalance or tell you if it's wrong or tell you, listen, some people would argue that this is, you know, predatory. I don't feel comfortable saying that. I don't know him. I don't know his maturity level. He might be really emotionally immature, closer to somebody in his early twenties.

40:24Emma Chamberlain:And meanwhile, you might be really like, I don't know. So I can't say that, but I can say to be careful. And I can say, you might be feeling that he's the most wonderful man you've ever met just because he has a really developed brain, you know, and you've been interacting with perhaps boys your age that don't have a fully developed brain. And that's not insulting. That is a fact. So maybe you don't need to date some seven years is long. Maybe let him go for a little bit and date perhaps some, you know, some guys who are a few years older, but within a range that is a bit more comfortable. you know, maybe stick to like three years.

41:06Emma Chamberlain:Yeah. Around there. You know what I mean? Maybe that, cause then you're getting a guy who's definitely a bit more mature, but not so much more mature that there's going to be a power imbalance or some sort of complication or discomfort around the age thing, you know? And then, Hey, maybe perhaps 10 years down the line, you two might rekindle and find love, but you, you also might not be right for each other at all. Um, only time will tell, but don't hold up. Let it go. It sucks. It hurts, but let it go and see what comes your way next. Somebody said, this is a very similar dilemma to the last one, but a little different.

41:45Emma Chamberlain:Somebody said, can an age gap relationship work? A man professed his love for me recently, and he's nine years older than me. Well, I've already discussed this a little bit. So honestly, I mean, I'm kind of going to sound like a broken record here, but the older you are, the better it works, right? Like if you're in your thirties and there's a nine year age gap, go for it. Forties, even better. Fifties. Wow. Easy. Do you know what I mean? The older you are, the more irrelevant the age gap becomes. But when you're in your twenties, a nine year age gap, you are at two very different phases in your life.

42:21Emma Chamberlain:I think, again, once you hit 25, probably it doesn't really matter anymore as much. Like from there, I think it's kind of fair game. Like who knows again, because your prefrontal cortex is fully developed. You are a developed adult, but like, okay, let's, let's think about it like this. I'm 24 right now. If I were to be dating a guy that's nine years older than me, that would be a guy who who is, what, 32? I don't know if that's right. It might be like 31. I'm not good at fast math anymore. I was when I was a child, but I've lost that skill. Whatever. 31, 32, 33. Around there. Okay. If it was a guy who's nine years older.

43:02Emma Chamberlain:Oh, if it's a guy who's nine years older. Wait, that's actually so easy math. 33. Wow. I'm embarrassed that I struggle with that. Oof. Do I think I could date a guy who's 33? Do I think that that would feel right? To be completely honest, I think it would be, it would be a little bit challenging, I think, because, you know, I'm somebody who wants to have children at some point, right? Okay, now if a guy is 33, I'm 24, I don't want to have kids for another, like, what, five years, maybe four or five years. Perhaps they would want to have children now. Like, it could be complicated, you know, different phases of life.

43:40Emma Chamberlain:Beyond that, when I talk to people who are in their 30s, it's interesting. Sometimes I feel like we're the same age, genuinely. Like I feel like we connect, like we're the same age. I don't think about the age gap. And sometimes I'm like, this is a full on, full ass adult beyond my comprehension at this time. Do you know what I mean? Like it varies. I don't know. I think an age gap relationship absolutely can work. I just think under 25, be careful, especially nine years. Ew. Be careful. Because as much as I think that every individual person is so unique and every situation is so unique that it's honestly irresponsible to make any sort of blanket statement, I also think that it's pretty safe to say that that large of an age gap under 25, for one member being under 25, I think is hard to pull off.

44:37Emma Chamberlain:And a lot of times it's sort of, it can be a red flag. It's like, why is this person dating somebody so much younger who has so much less life experience? Like there is sort of this question of like, is that a red flag? And obviously there are sort of the rare occasions where it's like, for whatever reason, there's just a click that's unexplainable. I'm not saying that that's impossible, But I think sometimes there's people who date younger because there's this appeal of like, they're not going to hold me accountable. I can manipulate them. I can sort of control them because I have all these years of life experience on them.

45:13Emma Chamberlain:I can convince them that everything I do and say is right because I'm older. I'm sort of the authority. And that can get sort of tricky. And I think once, you know, both people are past 25, 30, you know, whatever, that sort of disappears because everyone's a functioning adult. You can't really, that doesn't really work anymore. I don't know. So I really do think it depends on your age. And I would just say, be careful. I mean, obviously, this is all within legal realm. Okay, I'm not speaking, like, obviously, you get what I'm saying. Like, if you're 17, no nine year age gap, please. Let's not do that.

45:49Emma Chamberlain:that's very that's illegal so while the other person you if you're you get what I'm saying I'm not discussing that we're talking within within legal and in safe parameters here that's that's the guardrails of this conversation but you get what I'm saying I don't know it's tricky it is tricky but then I think about it and like I've met men in their 30s like well I'm 24 now so like when I was like in my early 20s earlier 20s like 21, 22, there were moments when I'd meet guys in their 30s and I'd be like, this is a child. So it's really tricky. Maturity is so complicated, but I wish you luck and safety and no power imbalance on your journey.

46:37Emma Chamberlain:Anyway, that's all I have for today. I hope you enjoyed it. And if you did, new advice session every other Sunday. New episodes of Anything Goes in general every Thursday and Sunday, twice a week, tune in. You can watch video and watch my FaceTalk on Spotify and YouTube and listen anywhere. And you can find Anything Goes on social media at Anything Goes. And find me on the internet at Emma Chamberlain and find my coffee company in the world and online at Chamberlain Coffee. I love you all. I appreciate you all. It's always a joy to hang out with you and especially give you advice. I love it, even if it's unprofessional and sometimes probably bad.

47:16Emma Chamberlain:I love doing it all the same. I'll talk to you all very soon. Love you guys and talk soon and bye.

From the publisher

[video available on spotify] welcome back to advice session, a series here on anything goes, where you send in your current dilemmas or anything you want advice on, and i give you my unprofessional advice. today's topic is relationships, and more specifically, when it’s time to move on from one.

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