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.
So last weekend I went out on a date with this girl. After dinner we went to my house and shortly after we decided to ride around. Well, when we went to my house, I went on ahead and changed into my pajama pants and a comfortable jacket bc it was cold outside. My pajama pants were a Grey plush fuzzy soft type material and my jacket was a black fleece columbia jacket. well we stopped by the lake and I was in that outfit when she started to rub my inner thigh all the sudden I feel a hard firm grip between my legs I remember a gasp and a feeling of shock come over me as I feel her grip getting harder. while all this is happening, she is talking about my pants. it was such a good pain, but im having a hard time processing the whole situation. Why would she grab my crotch like that?
I'm struggling to get over a guy named Prasoon. Even though some time has passed, I still find myself thinking about him. There's a song, "Shaky Shaky," that he once told me about. Every time I hear it, I'm transported back to the feelings I had when he first shared it with me and during our conversations.
Our relationship had its ups and downs. Eventually, he expressed a desire to live a "straight life," believing that being gay wasn't good for his mental health. Hearing this was a setback for me, and it made me reluctant to pursue him further. However, despite everything, I can't shake the feeling that we belong together. These thoughts constantly resurface and I can't seem to get past them.
One day, after a brief conversation, I asked him to cut off contact, and he agreed. Later, I asked him if he wanted to see me again, and he gave a clear "no."
Now, I'm at a loss about what to do with these persistent feelings of missing him. I wonder if it's just my hormones dictating these emotions, as Prasoon suggested
So I had sex with at a massage parlour. I did it from a place of loneliness and curiosity as i was a virgin before this.
I feel like shit now because i didnt live upto my family and religiosa values
I confessed this to my mom and she was very understanding and supportive.
Now, i am not in any kind of relationship but in future when i meet my future wife and I Will reveal this incident to her as I want to maintain transferencia and dont want to have a marriage built on a foundation of lies. How would she react to me? Imagine if you were my future partner, how would you respond?.
Just for some context, I am a 14 year old girl. I have been in my first serious relationship for a little over a month now. He's a really nice guy, he treats me really well and makes me feel loved and valued. But I think I've become too attached for my own good. My life seems like it's revolving around him and when I can see him again. I get really disappointed whenever he can't FaceTime or text me. Because it depends on whether our parents' schedules align, we've only been able to see each other in person twice since school ended and most of our interaction comes from video calls and texts. I fully believe that I feel a lot more attracted/attached to him than he does to me. When I'm talking to him, there's the constant fearful background thought of "What if he breaks up with me?" or "What if he doesn't actually like me?". Taking into account that we're 14 and have only been together for a month, I'm not sure if this is a normal way to feel or not. How do I stop being so attached to him? Should I talk about this with him or not?
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. 💔