Reddit Stories - UNEXPECTED PROPOSAL_ A CARICATURE, A Crowd, and a Ring_

Episode Date: August 7, 2025

#redditstories #askreddit #aita #caricatureproposal #crowdsurprise #ringreveal #unexpectedengagement #artisticproposalSummary:In a crowded park, a man proposed to his girlfriend with a unique twist - a caricature drawing that revealed an engagement ring. The unexpected proposal caught the attention of everyone around, creating a heartwarming moment.Tags:redditstories, askreddit, reddit, aita, tifu, caricatureproposal, crowdsurprise, ringreveal, unexpectedengagement, artisticproposalBecome a supporter of this podcast: https://www.spreaker.com/podcast/reddit-stories--6237355/support.

I hope you enjoy this story. Close companion asked for my hand in marriage in a crowded setting while I was having a caricature portrait created. I chuckled as we had never been romantically involved. He vanished and was subsequently apprehended by law enforcement. In all honesty, I'm still in shock that this happened so this might be all over the place. Bear with me. All fake names, etc. Jordan and I met in university two years ago. We both started at the same time and,

because of our ages we were both considered mature students. So we quickly became firm friends as we shared a dorm and we joke around together about us being old enough to be considered mature in our early 20s. We weren't on the same course, but given we lived together, we would hang out pretty much all the time whenever we didn't have a lecture. We joined a bunch of societies together, went drinking every weekend together, etc., etc. It was a pretty sweet gig because it meant we were at least never alone. Obviously we made other friends, both alone and together, but we were always each other's number one at the end of the day. At the moment we're on spring holidays for Easter. And while we haven't hung out constantly, we decided to make plans to visit each other's

hometowns, because we're from very starkly different places. Today, we went to mine. Mine is a big city central. This morning we went there and were wandering down the streets, doing some sightseeing, he's never been. There's typically a lot of street sellers here, trying to sell you everything from hot dogs to fluffy Pokemon hats. I decided I wanted to get a caricature done. I've never had one and I thought it would be funny to get and hang over my bed when we got back for term. I asked Jordan if he wanted to get in and he refused. No worries, so I sat down to get it done. They don't take very long, five-tenths-ish minutes, so I stayed look straightforward at the artist the entire time. He finished the caricature, I loved it.

So obviously I turned to show it properly to Jordan. When I turned though I literally don't even know what to say. He's down on one knee holding up a ring box. I don't even really know what he said, if he did the whole like proposal speech thing because I was so confused, I was barely paying attention. Remember again, this is a super busy tourist city, so this has drawn a mini crowd now, coming over to cheer us on. I couldn't help but burst into laughter. To be honest, I thought this was some kind of odd prank-type thing. We never have been prankster types or whatever, but I couldn't come up with a reasonable explanation. So I just laughed and laughed and laughed. Until I looked at Jordan and he looked genuinely heartbroken. So obviously I asked him something

along the lines of you are not being serious. This is the only thing I remember him saying. He shut the box, stood up, shrugged and said, I guess not anymore, and walked off. This left me standing pretty awkwardly in this gathered crowd of people, a lot of who were giving me dirty looks, which made me incredibly uncomfortable. The plan was to meet back up a hotel that we had booked rooms next door to one another. So I figured that's where he's going and head back that way. But he's not there. So I wait and I wait, and he still doesn't return.

I text him out of concern, this was at 1.15 p.m. It's currently 6.20 p.m. as I'm writing this, just asking if he's okay. He responds with a long message back, which I would post, because it's an odd read, but I won't out of respect for his privacy, in which he basically accuses me of leading him on, asking why I didn't break up with him sooner. Saying I had publicly humiliated him and that he thought I loved him the same way and that he felt our relationship was strong enough to consider taking the next step. Now this is completely out of left field. I literally have got no idea where in the world he's got this idea from. The closest we've ever physically been is a hug, hello and goodbye. I've never even jokingly flirted with him, for exactly this reason. I've had too many friendships collapse because they can't tell the difference between serious interesting and joking banner and friendships, so I've been extra careful to not.

We've never kissed, never been on a date, never had sex. I do not find him physically attractive and I wouldn't want to be in a relationship with him. I don't understand where on earth he's got this idea that we are. This isn't something he's ever bought up before this and I'm genuinely bewildered. He hasn't returned to the hotel yet, I periodically knocked a check, and I've been listening out for him walking up the hallway or anything. Nothing. I haven't responded to his long paragraph because honestly, I don't know how to.

I'm just so stunned and taken aback that I genuinely have no idea where to go from here or what to do. I haven't told anyone I know in person yet. Mostly because I don't want to bring this up to people who know Jordan. So here I am turning to strangers on Reddit instead. What in the world do I do update one? Hey, I'm not dead. I'm back at my parents' house at the moment and I'll be staying here until school picks back up in a bit instead of traveling around. It's nice to be home anyways.

Jordan did in fact not come back to the hotel. I stayed up until 1 a.m. before falling asleep and he didn't return. When I woke up the next day, the hotel staff let me know he had checked himself out at about 6 a.m. I did end up responding to his big long text. I took everyone's advice and told him that I was sorry it didn't go as he had expected but that I wasn't sure where he'd got the impression we were together. I said I'd be happy to sit and have a discussion about it all so we could make sure we're on the same page. He was not happy about this at all. And he again went off which a bunch of the same

type of thing he'd said in his first message. It didn't really seem to be going through his head at all. Even in these new texts he kept referring to this all as me breaking up with him, despite me explicitly telling him we are not and never have. Again, all his messages were very clear and coherent, even if what he was saying was not based in reality at all. He wasn't sending paragraphs, just sentences in really quick succession which was blowing my phone up. He told me he didn't want to meet up with me to talk because I had ripped out his heart and crushed it in public. I did ask him for specific instances he could recall between us that made him think we were dating, but he completely ignored the question and just kept going on and on about how hurt he was that I was breaking up with him

and how he felt his world was ending. He said he loved me more than anything and had felt so confident that I had two, which is why he felt so certain about proposing to move our relationship along. Eventually, to be honest, I grew pretty tired of the conversation and stopped responding, because it was just going around and around in circles. Me asking where he got this idea, him ignoring this and telling me how hurt he is I'm breaking up with him over this, etc. He went on and on saying he thought it would be a ring I like, because it was my favorite gem, ruby, instead of diamond. It's got me wondering how much he actually spent on this damn thing. I didn't look very clearly at the ring so I couldn't tell if it was something super

expensive or not, and that he had been working up the courage to do so for a while and figured doing it when I was at home would make it more special. For a while, he was just talking to himself in my texts, because I wasn't responding anymore. When I checked back about 20 minutes later, I had something like 60 messages from him. Granted, they were all one sentences. At the very end he apologized and told me that it didn't matter anyway because I wouldn't see him around anymore. Obviously I was concerned so I asked for clarification. He said that he was going to drop out of university and go back home because he couldn't deal with the shame. That's where our conversation ended. I didn't really know what to respond to that. As it stands now, I don't really know where Jordan is.

I didn't ask him, which is my bad. I'm not sure if, when we will talk again. I'm sorry this is quite a boring update. Unfortunately, I can't excite everyone with A and then he turned up at my door, and then he sent me flowers, or whatever. It feels a lot as unanswered. I still don't know where he got the idea we were saying from, he hasn't explained that.

So I'm sorry I can't give everyone that answer. I haven't reached out to his family yet. yet. I did consider it, but if he's not having a mental health crisis, I don't really want to involve them unnecessarily. Mini update, so adding on a lot of people said I should ask our mutual friends if he's ever bought this up before. Ever suggested we were dating, etc. All of the people I've asked, granted it was only five, said that they've not got a clue and he's never mentioned it before now. I don't know then if this is something that he's newly started thinking, if it's been something long-term, etc. Either way, in addition, I've also

screenshoted all of his texts, etc. Just in case. Reading back on them not with a slightly less confused mindset. They read pretty manic. Still haven't heard back from his mum just yet. Update 2, hey it's me again. Still doing okay and hoping this will be the last update I need to make, granted I thought the last one would be the last. I did say I wasn't going to make another update unless something significant happened. That's why it's been a week, so I'm sorry for the silence. Following my update post, Jordan's mom did message me back on Facebook, that same day.

We had a chat for a little while. She's a really nice lady she agreed, though, that this was incredibly out of character for Jordan, and in fact, she mentioned a few other things that she had noticed as being off about him in the last few weeks. Nothing crazy, just things here and there she'd never known him to do or say. I spoke with her at length about Jordan's mental health and potential psychosis, and she told me that there is a history of mental illness on his dad's side, including a paternal uncle's suicide, but that she doesn't know all that much about it because they've not spoken to one another in quite a long while.

Our conversation lasted about an hour, I showed her Jordan's texts, etc., and she agreed that they sounded quite manic, regardless of how coherent they were. A lot of people also asked if he had told our mutual friends and acquaintances that we were dating. I did message our mutual friends, our dorm mates, etc., and they all basically said they've got no idea what I'm talking about. So it seems he's just been sort of having these thoughts by himself without expressing them? I don't know how to get in contact with his close friends that we don't share, so I can't really ask them. Anyway, for a few days, that was it.

Until yesterday evening anyway, which is where the big and positive, depending on how you see it update comes. I got word from Jordan's mom that he had been detained under Section 136 by the police. For anyone not from the UK or who, like me, doesn't know what that is. From what I can tell it basically means he was suffering from an obvious mental health disorder in public, with their behavior concerning enough that they're a danger to themselves or to others, and police think they need immediate and urgent care. What I know from here is pretty minimal.

I'm not sure where he was taken to, but his mom, said that he would be there for the day while they perform a mental health assessment. So I assume that's what they're doing today. She said that essentially he had been out in the streets yelling about things. She didn't specify what, and intimidating other people on the street. He was throwing things around and generally just causing a lot of issue. Police got called because people thought that he was drunk. They established he wasn't, not sure if that's just from how he was acting, breathalyzer, etc.

I honestly don't really know how it works, and that's all I know. His mom and I again had a chat and we sort of assumed that mental health, psychosis is likely right. The rejection of the proposal probably set him into a spiral of getting worse in the last few days, bringing us to where we are right now. I do feel pretty awful about that. I'm doing my best not to blame myself, but it's hard not to feel like I caused it. Either way, way, he is currently with police, mental health professionals, etc. Likely being assessed.

I don't know how the system works, so I'm not sure what will happen beyond this point. If someone with more knowledge wants to chime in, please do. I'm hopeful, though, that this will mean Jordan will be able to get some help for whatever it is he is currently dealing with. My hope is therefore I won't need to update again, and this can end here. I have yet to speak to the university about the situation just yet. Not really sure how to, if I should approach that, so I'm leaving it be for now. This has been a whole lot of emotions, and I really appreciate the help of everyone on my last two posts.

Again, I won't update again now unless something major happens, but I highly doubt I will learn much more. If he gets diagnosed with anything, I'll see if I can find out what from his mom and I'll add it as a small update to this post, though some form of psychosis is definitely looking most likely. I don't want to bother her while they're struggling with this though, so we will see. Thanks again everyone, and thanks for following along. It's been really reassuring to have this support and people with way more understanding than I have to help me. Next story, wife and her best friend tried forcing their kids to date for years. When my son rejected her daughter's public proposal, she got bullied at school.

Then my wife demanded he apologize. This is a throwaway, but this involves some absolute high school drama nonsense that someone my age should have to deal with, but maybe I am trippin' and missing something. So, here I am. I, 45M, share a daughter, 17F, and son, 15M, with my wife, 41F. My wife's best friend, 40F, has two daughter, 18F and 15F. My wife's best friend moved to our town about six years. My wife and her best friend have been not so subtly pulling for the two fifteen-year-olds

to end up together. I find this weird and low-key creepy. About two years ago, Wife's BF's youngest daughter appeared to have developed a crush on our son. My son talked to me about it and he had zero interest. So, we discussed how to tactfully but firmly let her down. She has approached him again a number of times over the last couple of years and he has reaffirmed his lack of interest. This past summer, my wife's BF's oldest daughter turned 18. Her parents

went all out for her birthday. It was a whole weekend of festivities and events. One of the events was a couple's dinner for the oldest daughter and all her friends and couples. The younger daughter of Wife's BF wanted to go to the dinner but did not have anyone to go with. She asked my son, and he agreed to go, but only as friends and just this one time. So, they went together. After the dinner, the couples all watched ten things I hate about you together. It was my son's first time seeing it and he commented that he thought the Heath Ledger singing scene was cool, this is important later. My business partner, 44M, every year, for the last five years, throws a huge Halloween party. All our employees are invited along with close friends,

and family. The party requires a costume. And at this party, there are prizes for best individual costume, group costume, and couples costume. My wife's B.F. and her family are obviously invited every year. This year, the Halloween party is tonight, October 26th. So, let me get to the reason I am here. About a month ago, my son is at school and comes towards him as my wife's BF's younger daughter with the whole song and dance routine. She ends it by asking him to be her date for the Halloween party. My son was so frustrated and reiterated, for everyone to hear, that he is not interested in her like that at all. Of course, it being high school, some kids laughed and she ran off crying. She has been bullied pretty badly because of it. My wife's BF is livid and thinks our son

owes her daughter an apology. My wife agrees and thinks, at a minimum, he needs to defend her against the bullying. My son has said that for two years he has told her he is not interested and reiterated it over and over. At this point, he thinks it's kind of harassing to him and it is not his role to defend her harassment of him. I agree with my son. My wife and I have had a number of disagreements about it since it happened. Well, things have intensified in the last couple of weeks or so because another girl, who wife's BF's daughter apparently does not like, asked our son to be her date for the party and he agreed. They are doing a pretty dope couple's costume.

This has really pissed off my wife because she thinks he should, at least, not go to the party with another girl out of respect. I think that is ridiculous. I plan on driving them to the party with me. My wife now does not want to go to the party and is saying I am in awe and raising our son to be one. So, Ida. Update 1, November 14, 2024.

Given the events of the past couple of weeks, I thought I would give an update. My wife did not come to the Halloween party. I took my son and his friend and they had a great time. Unfortunately, only came in fourth in the couple's costume voting. After the party, tensions with my wife died down considerable. She still felt what I did was wrong, but she took a what is done is done attitude. The bullying at school has gotten more intense. Apparently, my wife's best friend's daughter confronted the girl who my son did take to the

Halloween party. That escalated the bullying from other girls and two factions have formed among the girls in two grades over this and it has gotten out of hand. Apparently some accusations have been thrown around about cheating at my son by various girls. My son has been unbothered because all his truly good friends know the truth. Last Friday we got a call from the school wanting to meet with us about the situation since my son was the source, their words, not mine, of the issues. We met with some of the administration and one of the teachers on Tuesday. They wanted my son to help the situation by defending my wife's best friend's daughter to their classmates. He refused and talked extensively about her harassing behavior over the past two years.

They pushed against his description of her conduct. But, we ended the meeting with my son promising to provide a list of her harassment over the past two years. Tuesday evening, my son prepared the list and showed his mother and I. When my wife saw the list, it was like scales fell from her eyes. She got pretty emotional, apologized to our son, apologized to me, and we had a good group hug. She is now 100% on our side. She asked our son if she could share the list with her best friend. My son agreed. My wife's best friend. My wife's best friend. response was to double down. My wife is going low contact for the time being. On Wednesday,

we took the list to the school. It is a private school and has a strict code of conduct for students in and out of school. So, there is a possibility best friend's daughter may have some type of punishment for her behavior. I took my son out of school for the day and we hung out all day. Just dropped him back off at school today. So, this is the update. I wanted to add something I said in the comments. My mom for years was a counselor. One thing she taught me is that repentance and forgiveness are not events, but processes. Also that in order for a relationship to be restored, there must first be repentance from the wrongdoer.

In light of that, a practice she had our family due was to write letters when one of us caused harm to another. The letter includes, in detail, one, the wrong the person has committed, two, the resulting harm that was done, three, the immediate actions that will be taken to mitigate the harm, and, for the long-term actions being taken to mitigate the harm slash ensure the action is not repeated. My wife is currently working on her letter. The person who receives the letter can respond and request that additional actions be taken to address the harm my wife know she is only at the beginning of the process and that it is going to take time. Update 2, January 18, 2025. This will be the final

update. After everything that went on with the school last semester, my wife's best friend decided to remove her from school, and she is now going to the local public school. But, a week ago, my son received an email from the daughter apologizing for everything that occurred last semester and asking for them to remain friends. Apparently her dad finally set her down and explained how everything she did would look from a guy's perspective. My son wrote back and said while he accepted the apology, he thinks it is best that he keep his distance. He wished her luck at the new school. My wife's best friend still insists that my son should apologize to her daughter. My wife has said, in no uncertain terms, that shit isn't happening. A few more kids were disciplined

by the school since my last post, but things have calmed down on that front. We are doing family counseling, and it has been going well. That is all. This is the final update. This is the final update. 8.