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 in my early 30s and since turning 30 I've been discovering myself again. I was in a 7 year relationship with a man for most of my 20s and I was also miserable and depressed most of my 20s. Just before turning 30, I finally seeked help for my mental health issues after the relationship ended and I realized I couldn't push my feelings down anymore. After some time I got help and got on antidepressants and got better. Before fully getting better I got into a situationship with a then coworker, who fell pretty intensely in love with me (according to him). I felt strongly too at the very start, he seemed really cool and all but as I got better mentally, I realized our personalities don't match. My depressed self liked him but my authentic self grew uncomfortable with him. He also pressured me into professing my love for him (like my ex did). Not long after that I kind of just broke it off with him, because I knew he was bad for me and I just wasn't satisfied. I wasn't working with him anymore, since I quit my job to study. I finally was all alone and I've been single like that for about 2 years.
I have almost no interest in relationship with men and I've actually started exploring the possibility of dating women. Tbh I haven't really thought about a proper relationship with women either but I've had some female crushes recently. I feel as though I'm coming into my full identity but am still hesitant to "come out" very publicly, which also means I don't use dating apps (I'm also very weirded out by them). I've always been pretty idk "queer" I guess, I had an online girlfriend as a teenager but it kind of freaked me out so it didn't last. But I've always felt some attraction to women. And I wouldn't deny it if someone asked, but I also havent really defined my sexuality nor professed it to anyone. Here is a good moment to mention that I am from a Nordic country, our culture is very repressed overall and I'm a very awkward and somewhat of a shy person. People would definitely call me weird and quiet. I currenty work at a place that houses young adults with mental disabilities, as a counselor of sorts. Last summer there was summer worker, a woman I found very attractive but she was so young and left after that summer.
There's also another coworker woman I've been I'd say... interested in for about a year. She's like a "permanent worker" idk how to else say that but she's like a regular, not a seasonal worker or a temp like me. Last year we didn't really have the same shifts and I very rarely even saw her at work. But the times I saw her, she left an impression on me since she's kind of a tomboy and seemed like a really cool person. She seemed different I'd say, and I have always been attracted to people who are different (even platonically). Finally, this year I decided to start doing more night shifts and I ended up on the same shift with her. It was an unconventional night shift also, because it was just the two of us there. There's usually 3 night workers doing rounds but one of our residents was in hospital, so the third night shifter was there. We talked a lot that night, I could see her getting more comfortable with me, since she usually never held eye contact for very long and seemed somewhat anxious before. I suddenly felt very brave and I held a conversation not to mention I asked a lot of questions. I felt I could really be good friends or even more with this person. After that shift I saw her occasionally at the start of her shift and the end of mine, as she does more nights and I do evening shifts. I was (and still am) always excited to see her and disappointed if I didn't get a chance to talk to her. Her eye contact got a lot better and she seems more attentive to me, as if she realized I exist after that shared night shift. I am actually really baffled how intense I am with her, since I'm usually very awkward and don't like eye contact with anyone. But her, I just stare whenever I get the chance.
This newly found confidence really came out this week, as I was finally again on the same night shift with her and another coworker. I can't even tell you how excited I was about these night shifts, even though last time we had more time together. But this time I came on pretty hard, even surprising myself. I think I might've gotten this courage from the fact that at the start of the shift we were talking, all three of us night shifters, and somehow got into talking about birth defects caused by acne meds and how women have to be on birth control to get the pills. She mentioned something about "having sex that you can't even get pregnant from" and I of course agreed with her sentiment on the matter. After that I just found every excuse to talk to her, to compliment her, to just be in her presence. I completely surprised myself and even felt kind of... proud? I ALMOST called her cute for getting so excited about a football match. She was watching some womens football in our tv room and I went out of my way totally awkwardly go there to be near her. I don't like sports at all but I made an effort to be interested and ask her questions about the game. I even at some point mentioned how the women playing are pretty. She was quite eager to tell me about football and I thought it was endearing.
I really made an effort to be interested in whatever she did or said. I even got a couple of chances to get really close to her and I just can't even... I really don't even recognize myself since I've always been the most awkward person ever. I'm not good socially, I'm weird and aloof and I never make the first step in social situations. This is so weird cause I know I'm really attracted to her, but I'm not afraid of her, like I've been of other women and men even. Am I just crazy, or do I feel some type of energy between us that allows me to be like this with her? I wish I could just... see her outside of work or something. There's a small chance of a get together that's being planned for August, where some people from work wanna just rent out a place and basically get drunk together. She signed up for it, and so did I because I saw her name. But idk if that will even materialize, or if I'll even be working there by the time this get together happens. Although if my work doesn't continue, I'd have nothing to lose if I just asked her out.
I also just found out that she is in fact 10 years older than me. I already suspected she's maybe late 30s or early 40s. She's very youthful tho, and I don't feel like we're really that out of sync, even with such an age gap. Oh boy idk, this is messing me up quite a bit and I'm feeling like some crazy person when I'm comparing our work schedules to know when I might have a chance to catch a glimpse of her. I don't really feel comfortable talking about this to my bestie, and I don't have anyone else to tell. I just have to vent somewhere. Also, heck, should I be worried that I keep crushing on coworkers?
I met a guy on a dating app, and we've since become boyfriends. He's 20, and I'm 22. We've been physically intimate to a degree, including kissing, and he wants to have sex. I'm unsure whether I should just go with the flow or think rationally before taking such a step. Since I'm older, I feel a sense of responsibility to ensure he is physically and mentally ready
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🫠?