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Dilemma Two Friend Dating My Ex
From 143. RUBY IS ENGAGED!! Ft Ruby Adler — Jun 16, 2026
143. RUBY IS ENGAGED!! Ft Ruby Adler — Jun 16, 2026 — starts at 0:00
Hey Tinies coming up on today's episode. I'm engaged . This ring is the best ring I've ever seen in my entire life so well. It's my dream ring and more. He goesever, you when'd leave the house, I'd get it and I'd have a look at it. We're both engaged at the same time. The two tins tie the night. We actually feel like I'm gonna get emotional . We've gone through so much. It was just the best moment of my life . Before we get into it, please subscribe to our YouTube channel at Wednesday's podcast. Enjoy the episode Timmy's back on the poll. Hi everyone. She's back from Mars . Yes . We bought some big pieces. You go, you go . I never thought I'd be nervous to say this. I'm engaged . We need to . I can't believe I can't believe that day five for being in. Yeah, so happened on Wednesday he proposed on my birthday. Maybe you should tell the girlies the whole spiel. Yeah, of like how it happened because no one's gonna know. No, they're not. So this is my big moment. Oh my god firstly, I'm like so happy I can't quite believe it. I knew we'd get married and I knew he would propose in time but I really just didn't think realistically it would be this year. So the whole thing completely threw me and I think a lot of people have inklings or spidy senses and they like kind of feel like I see a lot of videos on TikTok and Instagram being like, get ready with me whilst I think my boyfriend might close tonight. I don't like these videos. And I'm like, I watched them. I don't know why I don't. I kind of think it's incredible, obviously, but I just like that could not have been the opposite of what happened to me. Like I just sat down from coming home from the gym like it was my birthday, had my very average mundane morning routine as I always have. My boyfriend gave me a couple of really lovely gifts and we were doing incredibly lovely gifts, ruding cards . And I was in like I was actually got engaged in Tier's husband's T shirt , which sounds really weird. In Jay's T shirt that like I bought from like years ago that's like my I s like tears . And I'd just had a shower, been to the gym, sat down on the sofa, we did gifts, we did presents, we did cards, and it was such a nice morning. I was having my coffee. It was obviously my birthday so I had a lunch with a couple of girlfriends in like an hour or two. And Gab goes, Oh, there's just one more thing in the bag. I've got one more thing for you. And I'm kind of like clearing up packaging. And he goes, No sit down. I've got one more thing for you. And he comes out with a ring box Because my brain was so far away from getting engaged that I didn't see the ring box and put two and two together that he was proposing. So in my head I was like, Oh my god like you've got me a piece of jewelry or some earrings like, that 's so unnecessary. And then he sits down and he opens it, but he doesn't say it down on any? No. That would have thrown you off because I guess that would have initially been . He sat next to me and opened the box on the sofa and doesn't say anything . So we're both just staring at one another , right ? And I'm at this point computing what's happening. So I'm now realizing, Oh my god, this is everything I've like literally dreamed of my whole life . He's proposing to me. And like, it's been a hell of a year guys. Like I've literally like moved to Australia and like it's been like a really crazy ten years even like with relationships and with men and with ups and downs and like oh my god I actually feel like I'm gonna get emotional . We've gone through so much and actually in that one moment I was like oh my god like this is happening and I love him and he's amazing and I'm going to mar ry him and like it was just the best moment of my life . They were so good to he then say . No, so I then go to him , I go you asking me something. And the cheek of him goes, you know what I'm asking you ? Come on, just ask me and then I didn't say anything yes. I then didn't say anything and then he goes, so is it a yes , will you marry me? And I said, Yes, I will give me a little ring and I put it on and I was like and this ring is the best ring I've ever seen in my so well. It's my dream ring and I also do think for like and more. Yeah. It's the dream ring and more. But also the proposal like at home. I know you got engaged at home and like it was a special key and romantic intimate. The fact it was just asked, no one was like head to toe glam, like dun up like photo opportunities. It was so raw , it was so like special and actually like I almost felt like I'd blacked out like looking back like I know you have your proposal recorded which was just for you guys and you can look back at that. I feel like Gab isn't very content savvy. No, he's great at what he does but like he wouldn't have thought of like I'm gonna record this moment. You put it up in here yeah. So you've probably forgotten. At least you remember all the lead up and like actually how he said stuff. Oh yeah, I remember everything because there wasn't much that was said to be to be honest. But one of the first things I said to him when I realized what was happening and I, put the ring on . And he said, Well, you marry me. I think the first thing I said was do my parents know because obviously this is all happening in Australia. That was one of my first thoughts with moment you told me I was, I wonder if my mom knows? And he was like, Yeah, I spoke to her parents and I actually spoke to them both last night and I spoke to them before and I asked for your blessing and he said that my dad was really emotional. I know. When did he ask your dad? I think a few days before and then spoke to them again the night before about what was happening. Finally, they were preps. Yeah. And then so he did it at like half eleven AM Sydney time so all my friends and family had just gone to sleep . So I also then just to add, so after we get engaged, Gav goes, Oh, by the way, I've got a laser appointment now so I'm just gonna head to the house, I'll see you shortly. I'm dead. I didn't need to do it. And to be fair, it was my birthday and I was going to a lunch with a couple of girlfriends. So we then he had to go to an appointment. I was going to have lunch with my friends, which was always the plan. And then I just sat in no idea. No idea . And I sat in this uber on my way to the restaurant with no friends and family awake, hadn't told anyone, hadn't been able to speak to anyone, was going to see my two close friends in Australia and I was like, I've just got to hold out and wait to show them. And they were like, What? I was like, No . And then Gav came and enjoyed and we had some champagne, and it was just like, Oh my God, how love? And then the whole of the UK woke up. And then I felt like I got to relive it. So I wonder how you. Yeah, happy birthday, Tim. Yeah, I think it was eight o'clock in the morning woke up . And she just called me straight away and I was like, I'm not expecting you to call me straight away because it was your birthday and I wasn't gonna call you on your birthday 'cause I soon would be doing stuff. And then she's like, hi and I was like, Hi Merthi. She was like, and I'm engaged. And I was like, what? I scream recorded like all my close friends reaction. I've got such a good video of everyone and honestly Melissa looks absolutely . I like was as did everyone to be fair. Everyone was like, what ? Like what? You know, when someone's like about to get engaged and there's like you murmur it to your friends a bit like surely it's gonna be this year. Yeah . No . Absolutely . To the point where Tim was like, I thought probably next year, but I was hoping hoping it would be next year . But obviously I'm so thrilled that it's happened and we're so excited. We couldn't be more buzzing about this whole situation. I can't stop looking at it. You know what's mentor? I've not even met Gav . I don't know. I know how mental. I've never met him. She noticed about Gavin obviously living in Australia and us like dating is that there's no like, oh do you want to just go for a drink? It has to be like when we're like, Oh, what are you doing next weekend? Like fancy going for a meal? Because he's the other end of the world, quite literally ten thousand miles away. It's everything has to be so pre planned and then it's Christmas and dates don't work and then it's like summer holidays and everyone's so busy. So it's like we actually do have time soon in the next two weeks we'll get both going to be in Milka. So that's gonna be amazing and also what a lovely place to celebrate. Yeah, can't we? I can't wait to meet him. Your fiance. Fiance said that were . Yeah, so when we got on the plane , I can't remember how it was said, but Gab said to be like, Oh, this is where you tra to Lveondllingon. He was like, he was like my ' fcauseiance's family lived there and I was like And now we're talking wedding time . I know. I feel so grown up. I feel like a child bride. I'm like thirty one. So I feel like a teen bride. I do just need to grow up and this is just what happens, but like I'm like, Oh my god you're lovy age I also just like feel like so excited that like he's my life partner. Like he is the best guy in the world. So wonderful that's what it's all about. Like we have the best time together and I just like think he's the coolest person. I really do. That's so nice. Okay, cheers. Cheers also like we're both engaged at the same time and like and I think I told you yeah, I did on the pod about it was. like It I was the same, like five days out of engagement on the board. And I surprised you the day off. It was the best day. It was like the same thing. What can we call this situation? Yeah, can we name it like the terms take there's nothing tears about our wedding. Like Tim takes the two Timmy's tie the knot? The two Times tie the knot. The two Times tie the knot . Wow . I've never had this two resties engaged at the same time. Actually, that's untrue. Oh no, I've never had it. I've never known anyone. But I can think of two best friends engaged at the same time going through it. I can just think of Tim and Timothy So far Timothy, Timothy, who is going to be Timothy and who's gonna be Tim? I think I'm Timothy and I think you're Tim. Also I'm not Tim. You just renamed her. It's very confusing. Ruby's the origin al Tim. Tiny Tim from Scrooge. Yes with a broken neck . How appealing? And Sophie gave Ruby that name. He started it. And then everyone got hooked on it. And then Ruby was just desperate to tell me like why it was Tim. Like tiny Tim she's like, you know, from screwed. That's you. I was like, I wonder where she called that from? I can't stop looking at her ring. It's actually outrageous. We were at lunch and I was like, I can't listen to not I ab'smorbing anything you're talking to me about because I just can't stop fucking looking at it. It's so amazing. He's done really well. It's an actual rock on your hand. Like it's amazing . Did you what you wanted? Yeah, we'd spoken getting engaged, getting married, our future, what that looks like. Like we knew it would happen in time and he always asked me what my dream ring would be. Also what he likes. Like he's got a really great eye. He really loves like fashion, art and like night has appreciation for it. I feel like a lot of men stuff. I always knew I wanted something really simple and really classic and I kind of wasn't entirely sure on shape necessarily. And like I liked the oval, which is what I have . And I liked the idea of a really thin band, like quite Haley Brass. Yes. And then toyed with yellow gold and like he's just like he had n't gone wrong with what he's done. Like a massive gorgeous oval on the gold band. We've had stunning. It's like one big dive. Yeah, on a very simple band and that's exactly what he's nailed and it's lucky. And so I l feelucky and it's perfect. Like, I can't falter. This has been in the works since like Christmas. Yeah, Christmas, really? I don't know how these boys keep that to themselves and don't let it sleep. He said, he said he said to me, He goes, Whenever you'd leave the house, or you were away, I'd get it, I'd get it and I'd have a look at it. Wait, so he'd had it. It was made already . No, I think it was only made in the last few months. I think it got like suck. That's a long time to have to keep it in the house for months in the house before he proposed. Waiting for your birthday. And he was waiting for my birthday and he would like just have a sit there and have sit with it for a bit. And I was at the house and he'd just have a little look. He said he would always have a look when I was gone. I'd probably just practice just a film guess what Toby used to be. Yes, all the videos of Toby. But Toby probably got down on one knee. Yeah , which is the traditional way you do it. But did Gav just think did Gav just black out and was like I didn't even think about how I was gonna do it. He said he wanted to do whatever felt natural to him and it was in that moment felt like so because you didn't actually know what was in it until the box was open. He said he's seen disbelief life . He'd never I guess if you'd got down and then you would have been like, okay you are proposing and then it would have been open buted, because you opened it and in New York it also kind of opened it and I laughed I was like Ki like oh my god I wish I had a video of this one I would love to have seen it What are you going do to for your wedding band? You know, because I've said no, even though I'm like day, five engaged, I'm like, I wonder what I'll do. I think it has like a gap in it so I can like click in. Yeah, well it's like shape under nice. Sounded great. I quite like it. I prefer the look of what an eng agement ring without a wedding band around it. I think it's way chica, but I think it's chicer to say my wife than my fiance something a bit like I almost feel like I'm boasting and I feel embarrassed like I'm showing off . So I just say boyfriend. Do you? I can't bring myself to say fiancee. Can't. I have been saying it, but I don't know if it's 'cause I'm just day four or five. I've never said it in my life. Oh, really? I can't bring myself. But I can't wait to say husband. I think that's really cool and like I think it's really cheap. Yeah, I agree. But I think it's cool that I just have an engagement with no wedding band. I'm engaging because it's like a topic of conversation. I think being engaged is just so fun and like how like it just feels like young. Young, yeah, yeah. Whereas marriage I just think of my parents have been married thirty years. Yeah, so I'm quite happy. I'm engaged for that. It's at least a couple of years away. We're planning a big wedding and I honestly can't wait. But I also be that big. I don't think I'll rise will be that big. Come with . I don't think we'll have that many people. I think we'll do my wides, maybe. I think more do clothes you say that but when you when you add up your close friends and your family and then his . In my mind I'm like, let's have a small wedding and Joby's like, What's that? And I'm like, fifty, sixty people and he's like, Hey, that's just your friends. Yeah. I'm like, exactly , let's just have it work ed . But it does like when you add it in both people you then soon get to like one hundred and twenty people. And then all those close friends always have a boyfriend or a girl have it In the region of one hundred and fifty . Wow, okay. It's quite a solid nice number. Haven't sent out the same dates yet. I can't believe like we're going to have like your wedding's gonna fly by. Like it's actually not that long, is it? We were just talking, we need to get Ruby'sides Bmraid's dress at him. When I'm doing my like try on day, I'm not gonna be here. Timmy's not gonna be here so we're gonna try and dirt for. Yeah, we've got like a couple of options, haven't we? Also like you could just choose it online. Like you could choose the whole idea like trying it on getting the yeah, I know you're either. If I can, I'd much rather do that . Yeah . It makes it more of a thing. It makes it more of a thing we can make a day out of it. Like we could have lunch before and like it's also that makes me feel like I'm like supporting you part of that as well rather than me just ordering it online like I'm doing it with you. Is your sister your maid of honour? She is so nice. But like I've told everything I would like to have . And then she's like, A UK to have a few surprises? And I'm like, absolutely. You're like, I'd be like, Yes, give me all this. I don't want anything . I've banned pink . If someone wants to wear pink, fine, I don't want any themes . A veil for myself is great and then we call it day then and I just want everyone to be like dressed up vibes. I like that. I kind of like the idea of like boozy dinner then turns into a party. I love that. So do I. But like also like if it happens, I don't like the idea of all this everyone at night and all have to go out at midnight. Like when you read schedules like that, it makes my heart twitch a bit. I also don't want anyone to feel like they have to do anything. Love me planny handy like I know. I want it to kind of go with the flow a bit like obviously you need reservations and things but like the issue I don't want it to become this like I know hectic schedule I will say though at Sophie's end, we did go out once . No, we went out the whole time. Did we were so bad at the whole But I had so much fun. You and I felt upstairs coming back home but walking to our room, we fell up the stairs walking back. I've never been so consistently drunk. Actually, you know that's a lie the other week when I was in underwear I was consistently drunk. But like Sophie's was so fun and we went out but, like it wasn't like the wildest thing ever. Do you know what I mean? Like yes it was fun and we were boozy and it was and we were out it wasn't hung over yeah because we just kept drinking Yeah maybe that's why I just felt consistently like the right amount of p iss throughout the whole thing. Yeah. You know, there's some really annoying days, not that everything's about drinking , but there are some days where the alcohol doesn't hit and you feel like you're tragging back and nothing's happening. And you're like, it's just not hitting me in the right way and I'm over it and I want to go to bed because it's just not feeling right and I don't want to drink anymore . That didn't happen. It was like every drink. The hard greens and the champagne just went swimmingly. It was like day one of the hen . L Anducia, who's one of George's friends, who's so great, so funny. Fucking tanned. I can't even forget how she sits. Sit down follow her on TikTok now. Same, we follow her everywhere, every platform. Amazing. Sits down and she goes, I'll have a hard greens and a champagne. Mario actually like ordering coffee. This is like nine AM everyone's like a hangout. Starting the day like nice and civilized. I'll have a hard greens and a champagne, please . It was so it was so like classy the way she said it. And so dead paneria. Dead pan serious. Don't forget either of them. It sent us into like an oblivion of hysterics. And I don't think we recovered for that. It was so good. It was so fun. It was really good. And actually we were such a large group that I'm always getting there was twenty two of them. I remember thinking like, Oh my god, I'm nervous because there's so many people, but it actually did just work, didn't it? It was fine and there was like, you know what? Not too much of like a big group that all know each other and then a few on the side. It was sort of like pockets of two or three or four . And actually a lot of us knew and integrate grated so many times before anyway so it actually worked. But it is quite hard merging friendship groups sometimes. Yeah, it's like a birthday. You know, when you have a birthday, you're inviting everyone from all different like walks of life and you're like, Oh my God are they all gonna get on? But then over the years, as time goes by and you do those birthdays every year it you do see the same people ?. So Tr itue becomes a bit easier. So by the time you get to ahead and hopefully you kind of all know one another. Yes, that's true. Okay, should we go into some dilemmas? Dilemma one. Hi girls. My ex and I broke up in February. We loved each other, but one of our biggest issues was his anxiety around commitment. He cared about me, but fear stopped him from fully stepping into the relationship in the way I needed. Since the breakout, we haven't actually been in touch, which gave us both proper space. We've actually started seeing each other again at social events and that's brought us back into each other's lives. So you must have like a lot of mutual friends. Yeah, they've been in the same friend group. During that time apart, he started therapy and has done a lot of work on himself. He now wants us to get back together and he said he's a hundred percent sure. I've heard this story before . He's been very clear that he sees a future with me and he has spoken seriously about marriage. There is also a four year age gap. He's twenty six and I'm thirty . And I do wonder whether the part of the issue was simply timing and maturity . Part of me truly believes things could be different this time. We've agreed that if we do try again it would be very slow and honest with conversations first. But how do I know when giving someone a second chance is right versus repeating old patterns ? And how should families and friends' opinions matter when some are supportive but others are protective after seeing how hurt I was? I really would love some advice . Oh gosh We've both got back with ex I've got back with Toby and she's got a ring on it I guess it's like you kind of just have to go with your gut and like intuition slightly and if you like really love him and think that he's changed and that you're gonna but does he need to change? If he's having relationship anxiety, that's like something that he'll have to overcome no matter who he's with. Yeah, true. It's not like he's been a dick. No. It's just being hard . I know , I know. Sometimes it's easier when someone's been a dick, isn't it? You can kind of just go cold turkey and cut them out and like process things differently . I mean, I guess there's no harm in like trying because otherwise you're just going to continuously think what if? Like and then you want to watch him move on if you don't give him a chance you'll always be thinking about this guy that like wanted you back and you had this great relationship with and you loved but he, wasn't ready. And I think timing is so key and important . I guess like with four years age gap if you're thirty , you probably just want to check that you're like wanting the same things in the same time. In the same time that that has to happen like right here and now, but like you're on the journey to like wanting the same things with one another . Also like this anxiety thing will probably come and go and it's probably nothing to do. Like if it's the same sort of situation as like what Toby had like it was actually nothing to do with the relationship but because a relationship's like the one thing that's like closest to you. It's like when someone's in a bad mood you, take on the person closest to you, you then sort of cling it onto that like, oh maybe it's this, it's the issue . And then actually you find out it's not this issue's gonna follow me around like wherever I go . It's difficult when you've got like family and friends giving so much opinion but at the end of the day like he's not like been an awful guy. I think you should give him a second chance but I would really make sure that he's at a stage where also it might be helpful when you get back together. Like Toby and I would say the year after us getting back together was fucking hard because like ultimately he was still going through so much like relationship with anxiety and I was like you know I start being with me again and he was like kind of yeah like I know it's not you and I know it's not our relationship but, the anxious part of me is just going, Ah , yeah. And you have to kind of like not take it personally. Which is easier said than done when so hard. But also there's like a slight resentment from you, I'm assuming 'cause it's like, well, you've broken up with me. I've got back with you, how do I know you're not going to do it again? But like you're you're also taking a risk because you're like, I love you . But I want this to work. So I'm going to be with you because I believe that the outcome is greater than the anxiety , but you just want him to come back for all the right reasons, which is, I need to be with you, I want to be with you. I want to build a life with you, and I've made a mistake. We've got through this shit. Yes, with you. And people go through things, and people break up and people get back together and then they spend a lifetime together and they have never been happier and they needed to go through that breakup to realize that they're meant to be with one another. Yeah . But and I guess you don't know until you try, do you? Really? And you might be th alwaysinking what if? Yeah, which is the last thing you want to do. So Ice if you give it another go and it's another six to nine months of you dating him. If it doesn't work out, you'll then be like, I am done. Yeah, I've done yeah, I tried. it Yeah. I think that's what you do. Okay, love you so much. Good luck. I know what it's like. I do. I can really relate. So good luck. Okay dilemma too. Okay, right. Hi girls. I genuinely cannot believe I'm writing this in at my big age of twenty six, but here we are. Girls, my friend has started dating my ex . Don't like this. Don't like this. I feel like I'm losing my mind literally real life Amanda and Kiara from the summer house. Okay, I haven't watched this, but Georgia Habu has told me about it so I kind of know what you're referring to here. For context, she knows the full history and he teased on me and it literally broke my heart . She'd heard me unpack that whole relationships more times than I can count. So this isn't an odd realize you'd mind situation. She knew it would hurt me. I've already confronted her about it and somehow I came out of the conversation feeling like I was the crazy one. She got defensive, gave me the whole we just connected speech and basically implied I should be happy for her. The worst part is I didn't even want him back. It's the principle. It's the fact out of every man in this city sounds like Saxon city, every man in this city, she picked the one she knows I have history with, it's the Audacity. It's the girl code violation of the century . I love which she said it is. Now I'm stuck because we have the same friend group and I don't want to be the one who made it weird, but she is the one who made it the weirdest first. Am I overreacting or is this as insane as I think? And how do I exist in the same group chat as her without losing my mind? Okay, I think there's different I mean firstly , it sounds really quite awful. I think you need to weigh up like how close is this friend to you? Like if she sounds like she's one of your close friends which sounds awful and then like also I guess like he obviously sounded like a very significant part of your life. Like how long were you with him for ? And I guess it's not always a timestamp thing. Like even like if it was only a months, he obviously meant a lot. It depends on what your feelings are now. Yeah. I think it's very easy to look back and be like at the time he meant so much to me and like broke my heart . But now , do you still love him? Yeah, do you want to be with him? Does he still make your heart ache and does your tummy hurt when you're around him? Blah blah blah. If it's like, oh, I kind of get a bit nervy and butterflies purely because he's my ex but not because I actually have feelings for him. I honestly would just fucking let it go. Like if you don't want to be with him then don't good ridden. Honestly, like I do get it. It's obviously against girl code . But like if you've moved on from it, I wouldn't get hung up. I wouldn't like it's her problem now. I agree. I think that like if you really don't want to be with her and like what's the point of almost wasting your time and energy , like stressing and worrying about a situation. It's like you don't want him in your life as much as you can look back with like fond memories and like whatever happened with you guys happened. But then do you think it would change the dynamic ? So forget him him, you're over and you don't want him. Would it change the dynamic between you and your girlfriend? Like would you be like, So tell me everything like how it might be a bit awkward probably at least to jump try and just jump over that stage . But there is like, I guess it's frustrating when he's cheesed on you. He's been an asshole and he's called on your heartstring so much and you're like, now you're going to date him really. I don't know. I'm looking at this from so many different angles . I'm looking also Sophie and J amie like Sophie was good friends with Jamie's ex and then look at how wonderful and happy and Jamie was good friends with Sam. True. So and I'm like, you'd have to just be happy for people and then they're iconic cliff of like , I hope you marry her. Exactly. So I think if you agree with me, I don't know if think you're more annoyed because you feel like you should be. Yeah, I agree. Like I get he was a dick, just be like, I do think that you shouldn't have gone for my ex. However , I'm going to be happy for you guys. But I don't think it's worth losing your mind over and people it will just divide the group and I think you just that's the it's easier for you if you just you're gonna have a better time being okay with it than making an issue out of it. Good luck, babe. Good luck. I feel like I'm really anti girl code with that. No, I didn't know what time I really actually agree with you. I think we are all conditioned that way. And I hope for her sake that she has actually moved on anyway because it doesn't sound like he was very good to her. Good luck. If any drama on veils throughout this whole thing I want to know. Yeah, same. Love you. Love you . Thank you so much, Tim for coming on. Love you, Ruby, and I love your ring. Thank you both for pressing us at the present. Thank you for having me . Have the best time
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