There’s no such thing as risk-free dating. Whenever we put ourselves out there, there’s always a chance of making a fool of ourselves, having a heated argument, or just discovering our romantic interest isn’t that interesting.
However, humans aren’t entirely rational creatures, and instead of running away from a challenge, we might head straight toward it. “You miss every shot you don’t take,” and all that.
One online thread has people sharing what happened after they went out with someone way out of their league. Whether their endeavors come with a happy ending or not, at least they now have a story to tell.
#1
I started dating this woman, Athena, way out of my league. She looked like curated museum art, and I looked like misplaced furniture. We met at a dog park where her perfectly trained rescue sat like a monk, and my dog, Keeper, committed small acts of public chaos.
Somehow, she kept agreeing to see me. I spilled drinks, wore wrinkled shirts, and described my “portfolio,” which was really just a savings account called Emergency Pizza Fund. She found my disasters and ineptitude charming instead of alarming, which was either love or a very serious lapse in judgment.
I proposed at the beach, immediately dropped the ring in the sand, and screamed, “Please don't move, this thing is tiny.” She laughed so hard and she said yes anyway.
Ten years on, we’re married she still looks like luxury, I still look like chaos, and our wedding photos are basically “Model Marries Mikey the muppet.".
Somehow, she kept agreeing to see me. I spilled drinks, wore wrinkled shirts, and described my “portfolio,” which was really just a savings account called Emergency Pizza Fund. She found my disasters and ineptitude charming instead of alarming, which was either love or a very serious lapse in judgment.
I proposed at the beach, immediately dropped the ring in the sand, and screamed, “Please don't move, this thing is tiny.” She laughed so hard and she said yes anyway.
Ten years on, we’re married she still looks like luxury, I still look like chaos, and our wedding photos are basically “Model Marries Mikey the muppet.".
66points
#2
Still do, 14 years together and counting. The secret is to keep her laughing. She can't see you if her eyes are closed.
50points
#3
I used to think “out of my league” just meant someone more attractive. But being with her redefined that for me. She’s incredibly beautiful, sure, the kind of beautiful that turns heads without trying. That’s honestly the least impressive thing about her, though.
She’s thoughtful in ways that catch me off guard. She listens deeply. She remembers small details. She challenges me intellectually and makes me want to level up in every area of my life. Being around her makes ordinary days feel meaningful and worth living.
At first, I won’t lie, there was a little voice in my head asking what she saw in me. But over time I realized something incredibly important. The right person doesn’t make you feel small.
They make you feel seen. She doesn’t treat me like I’m “lucky to be there.” She treats me like a partner who is equal and one that she has chosen with intent.
So what’s it like dating someone I once thought was out of my league? It’s humbling in the best way. It pushes me to grow. And it reminds me that “leagues” aren’t real. What is real, is compatibility, effort, and the way you show up for each other.
If anything, I just feel lucky.
Not because she’s out of my league. But because she chooses me, and I get to choose her back every day.
She’s thoughtful in ways that catch me off guard. She listens deeply. She remembers small details. She challenges me intellectually and makes me want to level up in every area of my life. Being around her makes ordinary days feel meaningful and worth living.
At first, I won’t lie, there was a little voice in my head asking what she saw in me. But over time I realized something incredibly important. The right person doesn’t make you feel small.
They make you feel seen. She doesn’t treat me like I’m “lucky to be there.” She treats me like a partner who is equal and one that she has chosen with intent.
So what’s it like dating someone I once thought was out of my league? It’s humbling in the best way. It pushes me to grow. And it reminds me that “leagues” aren’t real. What is real, is compatibility, effort, and the way you show up for each other.
If anything, I just feel lucky.
Not because she’s out of my league. But because she chooses me, and I get to choose her back every day.
38points
#4
Yes, an extremely intelligent and gorgeous middle eastern woman who married me in 1970 and stayed at my side until leukemia took her away in 2021. Every day was magical.
37points
#5
We matched on Tinder and when I actually saw him in-person, in real life, I felt like I looked like Jim Carrey in The Mask, iykwim.
I had never seen a more beautiful man and that he was interested in ME?!? Even if it was just going to be a one night stand.
That was nine years ago this upcoming May— we got married in 2020, and I still look at him like he is the most beautiful man to have ever walked this planet, because he is.
And even better than him aging like your favorite fine wine, he is the kindest person I’ve ever met. He challenges me to be a better human, woman, partner, friend every single day. He is the most selfless and giving person I’ve ever known— he keeps a case of water in his car in the summer and a case of hot hands in the winter to pass out to panhandlers at intersections, because he sees dignity where others see waste.
Animals love him (even my hate-filled demon feline from the third ring of hell), kids adore him, and my life is infinitely more colorful and joyful with him in it.
I had never seen a more beautiful man and that he was interested in ME?!? Even if it was just going to be a one night stand.
That was nine years ago this upcoming May— we got married in 2020, and I still look at him like he is the most beautiful man to have ever walked this planet, because he is.
And even better than him aging like your favorite fine wine, he is the kindest person I’ve ever met. He challenges me to be a better human, woman, partner, friend every single day. He is the most selfless and giving person I’ve ever known— he keeps a case of water in his car in the summer and a case of hot hands in the winter to pass out to panhandlers at intersections, because he sees dignity where others see waste.
Animals love him (even my hate-filled demon feline from the third ring of hell), kids adore him, and my life is infinitely more colorful and joyful with him in it.
36points
#6
When I started dating a man years ago who had two Ivy League doctoral degrees including an MD from Harvard my friends all noted that he was way out of my league.
He turned out to be a full-blown psychopath.
He was in fact totally beneath me. Not all that glitters is gold, and you should never put anyone on a pedestal.
He turned out to be a full-blown psychopath.
He was in fact totally beneath me. Not all that glitters is gold, and you should never put anyone on a pedestal.
30points
#7
I never could figure out what he saw in me. I was plus sized and plain. He was athletic and gorgeous.
I remember him picking me up at school and a girl shockingly asked, "That's YOUR boyfriend?"
30 plus years later, i still don't know what he sees in me; but I'm glad he does.
I remember him picking me up at school and a girl shockingly asked, "That's YOUR boyfriend?"
30 plus years later, i still don't know what he sees in me; but I'm glad he does.
30points
#8
Yes and the weird part is the insecurity was worse than any actual problem in the relationship. She was objectively gorgeous and every time we went out I'd notice people doing a double take and my brain would go "they're wondering how you pulled that off." She never once made me feel that way; that was entirely my own thing. Ended up self sabotaging because I was constantly waiting for her to "realize" she could do better. Learned the hard way that if you don't believe you deserve to be there, you'll find a way to prove yourself right.
27points
#9
I went out with a woman for a short time that looked like a 6 foot tall Marilyn Monroe. At first, I would lose my train of thought while looking at her. That lasted about 2 weeks when I realized that she had never had an original thought. I see her online now spewing hate. Dodged a bullet.
26points
#10
My mate did. In his early 20s he went out with this incredibly beautiful and lovely polish girl who hadn't been in the country for that long. It was his first proper relationship and he wasn't out of her league; it was an entirely different sport.
They split up after about 2 years, quite amicably, when she returned to Poland.
It has forever realigned his expectations of a partner. We are now in our early 50s and he hasn't had a serious relationship since. He still, to this day, will dismiss potential great partners because they do not meet some aspect of his wonderful polish girlfriend possessed.
It is quite sad as he is nice guy but with warped expectations.
They split up after about 2 years, quite amicably, when she returned to Poland.
It has forever realigned his expectations of a partner. We are now in our early 50s and he hasn't had a serious relationship since. He still, to this day, will dismiss potential great partners because they do not meet some aspect of his wonderful polish girlfriend possessed.
It is quite sad as he is nice guy but with warped expectations.
24points
#11
It was awesome enough to turn my view on marriage. I swore for 2 decades that I wasn't going to get married. Been together almost 10 years, married for 6.
He is crazy clever, gorgeous, kind, hard working, and an amazing father. God knows what he is doing with me, but boy do I cherish that man.
He is crazy clever, gorgeous, kind, hard working, and an amazing father. God knows what he is doing with me, but boy do I cherish that man.
22points
#12
Yeah, and it taught me “leagues” are mostly confidence — the real mismatch is values, not looks.
22points
#13
Miserable, not because I was out of her league, I wasn't, i just convinced myself I was. Instead it was because I wasn't self aware to realise how popular I was, meanwhile that seemed to matter more to her than who I was.
It also partially made me realise I don't want someone who is out of my league, or even the league concept at all.
I want someone down to earth, who brings the best out of me, lets me be there for them, makes me laugh, have chemistry with me and is all about commitment based on respect and communication.
Someone whom I can share these finite moments with, who wants to walk the path with me. I want a human being, not a convenience tourist or self absorbed parasite.
It also partially made me realise I don't want someone who is out of my league, or even the league concept at all.
I want someone down to earth, who brings the best out of me, lets me be there for them, makes me laugh, have chemistry with me and is all about commitment based on respect and communication.
Someone whom I can share these finite moments with, who wants to walk the path with me. I want a human being, not a convenience tourist or self absorbed parasite.
20points
#14
Yup, very much felt that way with my current partner. I had to get out of my own head, my own traumas and insecurities were feeding an internal dialogue that they were out of my league.
Once I was able to tell my inner voice to [shut up] after some therapy, I am now in the healthiest and most compatible incredible relationship I've ever been in.
I was stuck in a pattern of bad relationships because i subconsciously thought that was the best I could have, that's total [nonsence] but it took some getting used to to not feel uncomfortable because the new partner behaved in a totally different way. That was a good thing but my nervous system needed to adjust. Now the bar has been raised by a mile. I guess that's why people say don't settle, it really can be exceptional. The attraction is unreal because they are hot [as hell] but they feel the same about me so who am I to say otherwise because I am insecure with myself.
Once I was able to tell my inner voice to [shut up] after some therapy, I am now in the healthiest and most compatible incredible relationship I've ever been in.
I was stuck in a pattern of bad relationships because i subconsciously thought that was the best I could have, that's total [nonsence] but it took some getting used to to not feel uncomfortable because the new partner behaved in a totally different way. That was a good thing but my nervous system needed to adjust. Now the bar has been raised by a mile. I guess that's why people say don't settle, it really can be exceptional. The attraction is unreal because they are hot [as hell] but they feel the same about me so who am I to say otherwise because I am insecure with myself.
19points
#15
Yes! Still together after 38 years! I was a waitress/party girl, he was a quiet, shy engineering student in college. Turns out we both thought we were out of our league but the perfect compliment to one another! He’s my best friend and we have a slumber party every night since the kid’s moved out! Also, I [am bad] at money so he has helped me with money management. I have helped him with social interaction/communication skills! Also turns out I probably do dumb things but am totally unaware it’s dangerous until he points it out to me?! He calls me his beautiful disaster and I call him my very handsome stable genius. It just works somehow.
18points
#16
Dated 3 10/10s in my late teens early 20s, all 3 were so boring. 2 were academically high achievers while one was just a normal girl living at her parents house. All 3 were so shallow and just so boring it would be hard to keep a conversation going yet they were still into whatever we would do and be having the times of their lives.
I remember one time at dinner I was asking her about how her first week doing an internship was going as the starter was being brought out and she said “I’ll tell you in one second” then took a photo for instagram spent what felt like 5 minutes doing her captions and filters or whatever and then asked “ what were you asking?” I asked again and she said “ it’s going great, I haven’t had pasta in so long should we order some?”. That moment was an awakening for me, as before that all I ever wanted was the hottest wife possible no matter what.
Keeping those relationships alive was harder and more exhausting than the physical labour construction job I was doing.
I remember one time at dinner I was asking her about how her first week doing an internship was going as the starter was being brought out and she said “I’ll tell you in one second” then took a photo for instagram spent what felt like 5 minutes doing her captions and filters or whatever and then asked “ what were you asking?” I asked again and she said “ it’s going great, I haven’t had pasta in so long should we order some?”. That moment was an awakening for me, as before that all I ever wanted was the hottest wife possible no matter what.
Keeping those relationships alive was harder and more exhausting than the physical labour construction job I was doing.
17points
#17
Dated a girl I met chilling in a park when I was 16. She seemed totally normal. Turns out her parents were worth £100m… found out when I was invited for dinner and turned up to some huge mansion. It was weird as hell, cleaners, chefs, butler, I could never get used to that sort of lifestyle.
She was cool but her family were completely out of touch with the real world. An example, I was invited to go with them to Alton Towers. We get there and they head straight to the entrance. I tell them I just need to buy my ticket. They were surprised I didn’t have an annual pass. Decided to buy me a 3 yr annual pass for all theme parks in the Merlin group (roughly £400. This was 2006/7 so probably like 1k now?) Ended after 9 months.
Edit: lots asking what happened. We mutually agreed our worlds were too far apart. Remember we were 16/17, she was very formal, dinner dates etc. I was a typical teen, all I wanted to do was hand around with friends, skate, drink. We had a connection, we had attraction but I think yeah, just too different.
She was cool but her family were completely out of touch with the real world. An example, I was invited to go with them to Alton Towers. We get there and they head straight to the entrance. I tell them I just need to buy my ticket. They were surprised I didn’t have an annual pass. Decided to buy me a 3 yr annual pass for all theme parks in the Merlin group (roughly £400. This was 2006/7 so probably like 1k now?) Ended after 9 months.
Edit: lots asking what happened. We mutually agreed our worlds were too far apart. Remember we were 16/17, she was very formal, dinner dates etc. I was a typical teen, all I wanted to do was hand around with friends, skate, drink. We had a connection, we had attraction but I think yeah, just too different.
13points
#18
Yeah.
I once dated someone I was 100% convinced was out of my league. Like objectively better looking, more confident, more socially smooth, the whole package. At first it felt unreal — I was on my best behavior 24/7. Overthinking texts, triple-checking outfits, trying to be “cool” instead of just being myself.
The weird part? They didn’t see it that way at all. To them, we were just two normal people who liked each other. The “league gap” mostly existed in my head.
It was exciting at first — big ego boost, not gonna lie. But the insecurity can get exhausting if you don’t deal with it. If you constantly feel like you have to earn your spot, it stops being fun.
What I learned: if someone chooses you, they’re not out of your league. The only real problem is when you start acting like they are.
I once dated someone I was 100% convinced was out of my league. Like objectively better looking, more confident, more socially smooth, the whole package. At first it felt unreal — I was on my best behavior 24/7. Overthinking texts, triple-checking outfits, trying to be “cool” instead of just being myself.
The weird part? They didn’t see it that way at all. To them, we were just two normal people who liked each other. The “league gap” mostly existed in my head.
It was exciting at first — big ego boost, not gonna lie. But the insecurity can get exhausting if you don’t deal with it. If you constantly feel like you have to earn your spot, it stops being fun.
What I learned: if someone chooses you, they’re not out of your league. The only real problem is when you start acting like they are.
12points
#19
Doing it now and it's pretty sweet.
I was in my early thirties. Single dad, solo parent. Hated the thought of dating but forced myself to hop on the apps for a few minutes a night, after putting my kid to bed and before I turned in.
Swiped on a girl, noticed we had something in common (both earned professional degrees). The more we chatted, the more I was blown away. She was a former professional musician and model; she left that career to become a literal doctor. She had a dozen Hollywood celebrities in her phone, and would tell me stories about working with them and their kids.
We'd meet up, she'd tell me stories about massive research projects and about recording music, and I'd tell her equally compelling stories about how my kid managed to get half of their pee into the potty for once.
Neither of us is sure why we got together. She'd been on the dating apps for years, and had decided strongly against dating single parents. She later told me that, if our initial conversation hadn't panned out, she was going to buy a townhouse and start adopting dogs as her lifestyle.
Anyway, we're getting married in a few months, she loves my kid even more fiercely than I do, and has declared that she's formally adopting him as soon as we're married so that we can truly be a family together. I love her to bits, and am still flabbergasted that she's committed to taking this journey with me.
For everyone out there, just make sure to always remember your own worth. You are more than just your resume or your physical appearance or your credentials. If you go into a relationship believing that you're worthless, the other person will pick up on it.
If you're seeing someone and believe they're "out of your league," that's just an invitation for you to better yourself to get into that league. After all, if you don't belong there, why would this person be dating you?
I was in my early thirties. Single dad, solo parent. Hated the thought of dating but forced myself to hop on the apps for a few minutes a night, after putting my kid to bed and before I turned in.
Swiped on a girl, noticed we had something in common (both earned professional degrees). The more we chatted, the more I was blown away. She was a former professional musician and model; she left that career to become a literal doctor. She had a dozen Hollywood celebrities in her phone, and would tell me stories about working with them and their kids.
We'd meet up, she'd tell me stories about massive research projects and about recording music, and I'd tell her equally compelling stories about how my kid managed to get half of their pee into the potty for once.
Neither of us is sure why we got together. She'd been on the dating apps for years, and had decided strongly against dating single parents. She later told me that, if our initial conversation hadn't panned out, she was going to buy a townhouse and start adopting dogs as her lifestyle.
Anyway, we're getting married in a few months, she loves my kid even more fiercely than I do, and has declared that she's formally adopting him as soon as we're married so that we can truly be a family together. I love her to bits, and am still flabbergasted that she's committed to taking this journey with me.
For everyone out there, just make sure to always remember your own worth. You are more than just your resume or your physical appearance or your credentials. If you go into a relationship believing that you're worthless, the other person will pick up on it.
If you're seeing someone and believe they're "out of your league," that's just an invitation for you to better yourself to get into that league. After all, if you don't belong there, why would this person be dating you?
12points
#20
I did for a short time many years ago. Just dated for a bit nothing serious. I wasn't bad looking by any stretch but she looked like a movie star. An 11/10
I did not realize how exhausting it is to be that level of attractive. She literally could not go anywhere without being ogled and/or straight up harassed. Nowhere in public was safe. Even when it was abundantly clear that she was on a date with me, even holding hands, there were several occasions where guys straight up propositioned her even with me standing right there. And I'm not even talking they asked her out, at least twice creepy dudes said some of the raunchiest nasty stuff to her. A stranger.
She said some days she didn't like to go out much because that just gets so obnoxious. She went to the gym in the middle of the night because it was usually pretty empty, otherwise guys would bother her constantly. I wouldn't have believed it without seeing it for myself. She was so hot that random guys on the street turned into disgusting animals.
GreatfulDeadHead: What ended the relationship?
I wouldn't call it a relationship. Maybe more of a fling if anything. She just kind of lost interest I guess.
I also had the sneaking suspicion that she started fooling around with another guy in my extended friend group. We were pretty much just friendly acquaintances at parties and such since we had a few friends in common. That guy was definitely in her league, super good looking and charming. A few of us had a low key inside joke that inviting him to a party was a party foul if one of us was trying to get laid that night.
I don't think it was intentional on his part, he was actually a really nice guy. Girls just threw themselves at him. More than a few times a girl asked me for HIS number.
I did not realize how exhausting it is to be that level of attractive. She literally could not go anywhere without being ogled and/or straight up harassed. Nowhere in public was safe. Even when it was abundantly clear that she was on a date with me, even holding hands, there were several occasions where guys straight up propositioned her even with me standing right there. And I'm not even talking they asked her out, at least twice creepy dudes said some of the raunchiest nasty stuff to her. A stranger.
She said some days she didn't like to go out much because that just gets so obnoxious. She went to the gym in the middle of the night because it was usually pretty empty, otherwise guys would bother her constantly. I wouldn't have believed it without seeing it for myself. She was so hot that random guys on the street turned into disgusting animals.
GreatfulDeadHead: What ended the relationship?
I wouldn't call it a relationship. Maybe more of a fling if anything. She just kind of lost interest I guess.
I also had the sneaking suspicion that she started fooling around with another guy in my extended friend group. We were pretty much just friendly acquaintances at parties and such since we had a few friends in common. That guy was definitely in her league, super good looking and charming. A few of us had a low key inside joke that inviting him to a party was a party foul if one of us was trying to get laid that night.
I don't think it was intentional on his part, he was actually a really nice guy. Girls just threw themselves at him. More than a few times a girl asked me for HIS number.
11points