Tales of First Dates, Connections, and Dating Adventures
Dating stories are filled with the excitement, unpredictability, and sometimes awkward moments that come with meeting new people and building relationships. From first dates that go incredibly right—or horribly wrong—to the process of navigating modern dating apps, these stories capture the joys and challenges of finding love in today’s world.
Some of the best dating stories involve unexpected connections. Whether it’s the person who turned out to be nothing like their profile, or a blind date that led to a lasting relationship, these tales remind us that the path to love is often unpredictable. For many, dating is a mix of fun and frustration, where every new encounter offers a chance to learn more about what we want in a partner.
Of course, dating can also bring its share of challenges. Miscommunications, mismatched expectations, and even heartbreak can turn a promising date into a memorable disaster. These stories, though sometimes painful, can be valuable lessons in patience, self-awareness, and resilience.
If you’re fascinated by the complexities of dating or looking for relatable experiences, dating stories offer humor, hope, and insight into the search for love and connection.
I'm proud to be gay. In this era of social media, heightened awareness, and AI, I've found that finding love is harder than ever. I've been hit with multiple rejections from people I liked; sometimes I couldn't trust them, sometimes things moved too fast, and sometimes it was my own mistake.
I've always believed I will find my right partner, but I wonder if I'm being delusional. Recently, I really missed one guy, but he seemed not to care and cut off our conversation. I'm skeptical about whether I'll ever be able to find my true love. I hope the universe is listening; I'm always waiting for him.
Do I want him, or do I simply just yearn for the feeling of being loved by somebody? Am I simply just bored, suddenly craving the attention of someone else while still having the full attention of him? I am a horrible person. I am undeserving of being loved; I do not have the capacity to be loved for anything but my measly little body. My frail feelings have me running in circles, eager to figure out... what is wrong with me? Why am I like this? I am undeserving of love. I see why nobody ever wishes to have me.
I'm struggling so much I have a boyfriend. A boyfriend of 1.5 years, and I have no idea at all if I still have romantic feelings for him. I always want the best for him, and I truly do want to see him succeed in life, but I just don't know if I love him anymore in that way. I've begged for months on end just for him to listen. to understand how I feel. He doesn't get it. He only wants to change when I'm beginning to slip from his grasp, and it's the worst feeling in the world. Only now that I'm starting to lose my care factor, he wants to fix the issue I've had for a YEAR. It feels so horrible. To add to that, my guy best friend is being really weird .. like oddly affectionate. It has me feeling ... confused? causing my struggle to worsen, even? And not only that, but he has been borderline encouraging me to leave my boyfriend.
I'm so confused .. lost, even. I don't know what to do with myself. It doesn't help I'm struggling with severe depression (5 years, ongoing).
Being gay is so painful; finding love feels like an insurmountable challenge. To those around me, it might seem like I lead a chaotic life, but they have no idea this isn't a choice I made; it just happened. Everyone has different perspectives on gay people, and I've even encountered some gay men who are homophobic, which still doesn't make sense to me. I'm not feminine, and none of my friends know about my sexual orientation; they all think I'm straight, and I've maintained that status quo.
I wish I could talk to them about my dating experiences, but I can't. It's equally difficult for me to find the right partner, and the world feels so harsh. I don't even know how I'll manage in the future. People call me 'hot,' but I don't understand why guys don't seem to like me that much; they often say we can't have a future, and I don't have an answer for that.
I just wish I was never gay. Would my life still be this difficult? My emotional health is suffering, and I have no one to talk to. I'm all by myself, trying to fix myself, feel better, and live a decent life.
Experiencing multiple betrayals and being left alone has made me lose faith in love, and I constantly wonder if I'll ever be normal again or find the right person.
I feel so wasted for giving my best to someone who didn't care. I've started to hate myself, questioning why I can't live all by myself, and thinking how wonderful that would be. I've begun to believe that people are heartless and don't deserve to be loved.
I love this guy so much. I love him so much that I wish he would understand that it's torture to be left in the dark about how he feels. We got into a situation where I was honestly being very emotional and hysterical for no good reason. I asked him if he would ever tell me if he had an issue with me or anything that he ever wanted to talk about so that I wouldn't spiral so badly again and he told me that he would never. I was shocked to say the least. It's important for me that there is communication in a relationship and I feel like we have awesome conversations when we are just talking, but we can never sit down and have a conversation about anything important. He internalizes a lot of things and I feel very cautious of what I say around him because he remembers very little comments and brings them up when we fight about anything. I match his energy and I keep things to myself and when I eventually explode and have horrible reactions he either just brushes off my emotions with "ugh men" or he talks about how he could've never known I felt that way and that I should talk instead of keep things to myself, when he is the worst at doing that. He makes me feel like I'm insane or dramatic and he often calls me dramatic, but I don't know if I really am or if I'm normal? We have both had bad experiences with dating in the past, so of course we're gonna have our baggage, but I really want this to work. He recently has talked about moving back to his home state with his mom and how he wants to get a one bedroom apartment and I was afraid that he meant alone and my emotions are clear on my face usually so he saw and he told me that of course he meant with me, but I really feel like I can't trust anything he tells me. He is very good at putting up a facade, it's kind of chilling how he can do that honestly because one day he was talking to an old friend and being very chill and laughing with them and immediately after that he just straight up cut them off entirely. He had reasons why he did that and I understood that he felt uncomfortable with that friend for a long time, but it put a big fear in my heart that I would wake up and he would just be gone one day. How would I even explain that to people? I have been through something similar with an ex that I had in high school where we stopped talking and he broke up with me and blocked me. I feel like this is worse though because I am not even sure if he would TELL me before just straight up blocking me.
[Translated from Spanish. Reminder: IIWIARS is English only]
I’ve always been very insecure and jealous in my relationship, somehow he made me feel that way, even though he never did anything wrong. I have his Instagram logged into my phone and I was always checking what he was doing. Until I decided to check his TikTok video history. I found a series of videos of a beautiful woman. I said the girl’s name to him and asked who she was, he said he didn’t know her, and I kept insisting, saying I knew he’d watched her. He said he thought she was pretty. Now I feel insufficient, stupid, ugly, trashy, and everything bad there is. I don’t have the courage to break up, and I’ve already cried a lot and he comforted me, apologized, and all that. What do you think I should do? But he always knew I felt insecure because I always opened up to him, but I know there wasn’t much to do, because he never gave me a reason to feel insecure or suspicious. It’s very hard to break up because a big part of the time I’m with him, I’m happy.
So me and this girl have been talking on and off for about a year, to be specific within this year the reasons we've ended things we're she was over stressed by school, she didn't want to ask me to change and she felt like we were to different and I mean it's my fault for having my standards so low to even take her back because every time we ended things it's because she wanted to but about two and a half months ago she wanted to start talking again but just as friends, which is totally fine but what I was aware of is the fact she would be talking with other guys while talking with me. The way I found out is bc we work together and that's how we met and so we were on shift together just having fun laughing and then one of my friends walk in and I walk up to him calling him by his name bc this is one of my closest friends and like after our shift together she requests to follow him on Instagram and my friend texts me and he's like "do u know who this is" and I'm like "oh that's the girl I'm talking with, she prob heard me call u by your name while at work" and yk I fully trusted this girl so I thought she just followed him bc he was my friend and no other reason but then I started telling her about it and when I told her about the part of me saying that's the girl I'm talking with she blows up in my face and is like "what right do you have to put labels on us, I followed him because she caught my eye and you have no right to interfere" but like I was under the impression that we were fully just trying to work things out between us and it's not like we've just been friends per say I mean litterally the day before she was talking about how jacked I am, and the day before how cute I am and then the day before saying she was shaking because I almost saw her without makeup and then like a week before that saying she was concerned that it seemed like I didn't like her anymore
and like what am I meant to do? I liked this girl so much but I can't just take that laying down right? and I mean I haven't talked to her since but I have to see her at work on Sunday
I just need some advice on the whole situation, maybe I'm being over dramatic and I'm wrong but I feel like I'm being an idiot.
There's a guy I have met in dating app with him I wanna have romantic feelings with him but he has friendly feelings n said he wants to friends and slowly develop into something but idk how long will it take. He said his past was not good because of hurry relationship n stuff.
When he was online in app I was really jealous but he told it was because he saw old friend n chatted in his hometown.
Then he compared his friend with me I was devastated.
I told him i will move on clearly but in reality idk what to do.
Heyah👋🏻😄!!
I'm a short girly, and I was wondering if being short is a good thing when choosing a person to date🤔? I'm also 24, and I worry that my 4 foot 11 inch tall frame might make dudes think of me as a child🫠? I get the "you're super cute" instead of "you're super pretty/s*xy" sorta thing.
Also, because I'm super short my body proportions might seem a bit odd, as I have a size H bust... And that has confused a few of my male and female friends, cause I look like one of those anime characters who's child-like but has an "unrealistic" chest size🥴. They're real by the way, and I've always wanted size C or D, but..... Money😭💸!!
So, I'm asking the public... Anonymously, if my short stature, and front watermelons would turn people off🫠?
It’s kind of stupid. I don’t even really know how to say it, or why I feel the need to throw it out here. But here I am.
Today’s my ex’s birthday. We broke up over two years ago. We were together for four. And still, every damn year, May 16th hits me like a total bitch.
I try to carry on like it’s a normal day, but it’s not. It never is. I close my eyes and she’s *right there*. The memories come rushing back before I can stop them. Not really the good ones, even though there were a few, but mostly the bad. The heavy. The ones that never really let go.
It was the worst relationship of my life. I’m really not exaggerating it. I’m won’t get into the details—this isn’t the place, and honestly, I don’t want to go back there more than I already am. But it was toxic. Emotionally violent. Draining in ways I still don’t have words for. And yet—part of me is *still* stuck there. Still trapped in a past I hate with every part of me.
I’ve tried to move forward. Tried to rebuild. And on the outside, it looks like I have. I’m stronger now. Sharper. She’s been gone from my life for ages; we don’t talk, we don’t see each other, we live in different worlds. But today, I can’t fake it. I can’t pretend May 16th doesn’t mean something. That it doesn’t *still* mess me up.
I hate feeling this way. This ugly, twisted mix of pain, nostalgia, and quiet anger I don’t know where to put. It makes no sense. I didn’t ask for it. I don’t want it. I don’t *deserve* it. But it’s here. So I’m saying it. Because maybe it’ll helps. Maybe dragging this invisible weight into the light makes it just a little easier to carry.
sometimes, I find myself perplexed by my attraction to men. at 29, one would assume that I have gathered sufficient wisdom to navigate the dating landscape, yet here I am, grappling with a recurring frustration. my experiences with men have ranged from enriching to utterly disheartening. it's as if they oscillate between interesting conversations and exasperating behavior that leaves me questioning my choices. is it merely a matter of societal conditioning? or is there something inherently captivating about the male psyche that draws me in despite the red flags? 🤷♀️
more than once, I have encountered individuals who showcase traits that are both appealing and maddening. for instance, I appreciate a good sense of humor and intelligence, yet these attributes often seem to coexist with a lack of emotional maturity. it is frustrating to witness men flaunt their charm, only to retreat into a shell when the conversation turns serious. I wonder if this is a common experience or if I have a knack for attracting the emotionally unavailable. could others share their encounters? it leaves me pondering why I persist in seeking connections that feel so inconsistently rewarding. the highs are exhilarating, but they inevitably lead to lows that feel all too familiar. 😕
while I understand that every individual is unique, the patterns I observe are hard to ignore. the initial thrill of a promising date quickly dissipates into moments of uncertainty; am I asking too much? do they even realize the impact of their actions? trying to navigate this dating scene feels like an uphill battle that I am somewhat reluctant to fight, yet I continue to feel drawn to it. perhaps, I question my own motivations—what is it about men that keeps me returning for more? the search for companionship is universal, but the road to finding it feels uniquely fraught for me. maybe it's time for reflection and a deeper understanding of what I am truly seeking in this complex game of love. 💔
Is it messed up that I slightly hope the the girl I’ve been talking to goes to jail so I can stop talking to her because I’m struggling to not to talk to her because I’m so alone, and I know she uses and manipulates me and it’s destroyed me emotionally. She goes to court tomorrow and idk how to feel happy because I can not be used or sad because I’ll be back to completely isolated . For a bit more context I met this girl at a club she right off the bat tells me she’s a felon but she likes me, I get her number and we go on a few what I think are dates but really just me paying for her dinner and I get to join along And she gives me just enough to keep me around and hooked but not enough for anything else and she tried to avoid most all conversation I try to have about anything and then calls me a creep to my face for trying to get to know her even though she has never asked me one question about myself and she’s never sales I don’t think this will work or I’m not interested she has said she is interested but doesn’t act like it
Me (14F) and my bf (13M) have been together for a little over a year now, but things have been not so good. We are long distance so we can only text and call, we wanted to meet up when we were older but things have changed. Last night me and him talked about taking a break or breaking up. He has been mean to me for the past few months and didn’t really treat me like his girlfriend, he let his friends be mean to me and he just laughed even though I’ve cried to him on the phone several times because of it.
But we both said if we do breakup, it would be on good terms and we would still talk and be friends. I do love him but the relationship wasn’t healthy for really either of us and often hurt me mentally. I still love him, I really do. I loved how sweet he was when he was and I just love everything about him other than the way he treated me. I feel like the distance is a big part of it because touch is my love language and also an easy way for me to show emotion in a few ways. I don’t want to breakup but it’s for the best.
My only issue is that I don’t know how I would find a new boyfriend when I’m ready. I’m homeschooled, there’s no clubs in my areas that I’m interested in, I don’t wanna do long distance again, moth of the guys/people is my area are assholes…I might have to try an app to meet someone but I’m scared of apps because of the risk of pedophiles and such. I just don’t know what to do
I'm struggling through a break up. It was a three year a relationship with someone I thought I was going to marry and have a future with. We decided to remain friends because we still love and want each other in our lives, even if it means transitioning into a friendship. We are currently going through a period of no-contact to give ourselves a grace period before we try to make a friendship work. It's been hard. Although I love the freedom and flexibility I now have, thinking about them moving on and trying to move on myself hasn't been easy. I've been struggling physically and mentally. It's been affecting my work, not by much, but I do see myself making mistakes and slowing down drastically in terms of work ethic. I know this is for the better, but I still get moments of wishing I could go back and crying over this. It doesn't help that they make it look like they're having an easier time transitioning through this. I know that's such a selfish assumption and people grieve differently but I guess there's a part of me that feels like I'm the only one struggling. I don't know what I'm trying to do. I'm trying to get back on my feet at work and pushing through with enrollments for my master's degree. I'm scared I won't find love anymore after this, and honestly I don't know if I can do anything better than what I had with them. I'm just not doing so great. Unlike my other breakups though, this one has no hatred or anger involved, it's just the yearning and mourning over something I was building my life for. I don't know how to go on... I mean, I'm trying my best but I don't know...
Context: I was with my ex-boyfriend for a little over 2 years. It was definitely rocky, especially toward the end, but the break up hurt. It hurt so bad because it was abrupt, and it was like right when I started liking him again. I became the desperate ex for like a little just trying to get back with him or at the least stay friends. It didnt work after he asked me for advice on how to date a new girl like 3 days. I blew up on him for being an asshole and he blocked me.
Fast forward about 3 months later and I started dating again. I accidently got into a serious relationship while in retrospect, defintelly still having feelings for my ex. I declined my feelings and moved forward with the new guy. Fast forward to this past summer and I cannot stop thinking about my ex. I wasnt happy in my current relationship so I didnt care to hide it. I told my current bf and said I need to reach out to him. He allowed it and things did not go well with my ex. I end up blocking him. Fast forward about 6 months and again he consumes my mind. I dont reach out as I know theres no point but I still want to.
I want so badly to be as connected as we were. He was funny, playful, cocky, but most of all real (or atleast it felt like it). Ive come to understand that I dont like him, but l miss the way I felt.
Today, I feel so empty. My current boyfriend just makes me anxious and judged. I dont love him but I want to because he is a good guy.
Yesterday I asked him, if I dissapeared, do you think I've made an impact on you. He said no. Hes told me he doesnt think I'm funny, he doesnt think Im smart, he just does not like me.
I want so badly to leave him. With college coming up, I told him I want to break up and he said no. I tried to pushback but it was still no. With me being such a coward I took his answer. I should stand on my ground but I dont.
Ive put myself in this situation and I just want advice.
I feel like I havent explained my situation the best I could and definitely left some things out. But, how do I get the ex off my mind. How do I salvage or break off this relationship.