I was a classic ugly-duckling.

Bullied in elementary school and middle school, so I had no social skills by the time I reached high school. I was a stress eater in high school and was overweight due to social and general anxiety, I didn’t have any sense of style, I kept 1-2 close friends but was really a hermit for the most part.

College comes around and I decided that I wasn’t happy, I was going to “find myself.” I slowly started getting healthy and in shape—I’ve lost about 80lbs of fat in the last 6 years and have put on flattering muscle. I experimented with fashion to find what works for me, it’s now rare that I leave the house without a friend or stranger giving me some sort of compliment on my clothes. I waited tables to pay for school which really forced me to come out of my shell and get used to talking to people. I’m still working on my social skills, I “foot-in-mouth” a lot and don’t makes tons of friendships that go beyond surface level, but I’ve been told by a lot of people (dates, strangers I served in restaurants, family friends) that my whole energy can light up a room.

I’m generally happy and consider myself a well adjusted adult, I have hobbies, I’m educated, I have a great job. But I keep having the same problem where dates and boyfriends think I’m too good for them and I don’t know what I’m supposed to do.

I’m pretty limited at the moment to dating apps. But I routinely have guys un-match me after a bit but they’re sure to tell me“you’re too pretty and funny not to be a catfish” first.

I had a single date over Christmas with a guy who said his office had a running bet that either I was a catfish or I was going to stand him up because he wasn’t “in my league.” After the date he told me he didn’t want a second date because I was very much out of his league and he didn’t want to deal with that.

I have had guys from apps ask for my phone number and the first thing they ask for is a picture of me holding up x many fingers to prove I’m real.

My first serious boyfriend in college developed an anxious attachment to me, he’d never had one with any other girlfriend. If I wasn’t reassuring him a dozen times a day that I loved him—when I woke up, and yes after lunch I still loved him, and even though we’ve been silent for 2 hours at the movie theater I still love you—he’d panic and ask me what changed, why didn’t I like him anymore. I eventually broke up with him, it was one problem of many but it was exhausting.

I ended my second long term relationship, during the break up he said he knew we were never going to work out because he was clearly “dating up.”

My most recent boyfriend routinely told me I was perfect. I told him he shouldn’t think like that, I have flaws, it puts me on a pedestal and when I fall it’s going to be unfair. He also developed a cuckolding kink while we were together. He said it was specific to me. He’d never had an interest in the kink prior to me, we’ve remained friends and I asked, he doesn’t have that kink now. It was 100% based on me. He said that he wanted me to be satisfied by someone else because he wasn’t capable of it, couldn’t live up to what I needed, I deserved better. I told him he was hands down the best I’d ever been with, I was happy and satisfied, he would change the subject but it got to the point where we couldn’t have sex without him fantasizing about me sleeping with “someone better.”

I realize this probably sounds whiney, poor me I’m too good for dating. But what exactly am I supposed to do? I have absolutely no idea how I’m supposed to go about dating when people either don’t believe I’m a real person, shoot any relationship down because I’m out of whatever league, or my relationships come with this pedestal I’m inevitably bound to fling myself from.

EDIT: I just wanted to say thank you to everyone. I’m still reading and responding to replies, but this has been a really kind, engaging, and respectful discourse. I know reddit often devolves into the disciples of harsh truths and was fully prepared for that. I was mostly looking for a place to vent, but hopefully find some advice along the way, and for whatever reason everyone who responded has been really lovely, so thank you!

36 comments
  1. I also ugly ducklinged and although I don’t think I’ve experienced what you have to the same degree, I have nevertheless. My takeaway is that it’s not a problem with you it’s them, they’re just insecure and lack confidence. It’s ultimately better that the ones who struggle to believe you’re real or think you’re too good for them show those feelings now bc they’re the ones who will develop really unhealthy attachment styles. And it’s better to find that out sooner or later.

    All it really takes is for you to come across a man who has the self confidence to pursue anyone regardless of whether that person may be “out of their league”. I mean look at Pete Davidson, the guy arguably only dates out of his league. And that’s certainly not bc he’s telling these women that they’re too good for him or that they can’t be real.

  2. I have total faith you’ll eventually find an egotistical guy who will take you for granted no matter how amazing you are. Jk. I’ve never understood the whole “league” thing really because it should be way more important what someone’s personality is than their looks. Maybe instead of trying to date use your hobbies to find a friend and build that up. The best relationships in my opinion are always the greatest friends, and they would already know the real you before they got the idea you’re too good for them? Maybe.

  3. I totally believe your story and yes that sounds hard. Just be your authentic self. Focus on your most haves in dating. What is most important in a partner. Career, religion, kids, hobbies. Then looks. Be honest with guys that you like. Even mention you had a glow up but that doesn’t mean you are going to leave them for a pretty face. And don’t put up with insecurities. Be your best self.

  4. I like you.

    I might not be “in your league l” physically but I’m not insecure what so ever and I am comfortable being with woman who are supposidly “out of my league”.

    I’d go on a date with you

  5. Ugly duckling anti social, just being myself forever and always and happy to be me. The world sounds alot nicer with you around 🤗🤗 keep it up and stay the course, people sound competitive I’d take that as a compliment and enjoy your life 😊

  6. I *have* to see a photo…

    You just have to keep trying. I find it very hard to believe that you won’t find someone compatible soon. How picky are you?

  7. Lol, I appreciate the internet’s never ending curiosity, and that the content of my post probably compounds that, but I’m not posting to prove anything to anyone. Just looking for some venting, commiseration, and advice if people have it. Sorry to disappoint!

  8. Im sort of in the same boat and I absolutely hate this… I get told the same, and it leaves me defeated, alone, and chips away at me as a whole . I’m sick of positive feed back about my character, appearance, and what I’ve accomplished only to end up single or not the chosen one because I’m “too good” for them. It infuriates me to my core.

  9. You’re speaking of an increasing societal problem caused by social media, online dating, and pornography — *namely, the average man’s confidence in himself is likely at an historical low.*

    Sadly, this lack of confidence causes the average man to exhibit neediness instead of strength. Women perceive this weakness, whether consciously or not, as rightfully problematic and unattractive. Though many women do not want kids, they are still *subconsciously* attracted to the traits that would be helpful to providing for themselves during pregnancy and also their hypothetical offspring. If a man does not believe in himself enough to feel worthy of a woman, how can he be confident enough to help provide in a harsh and unforgiving world?

    There’s nothing for you to do but find men of confidence. Go to events such as networking events, entrepreneur meetings, the gym, perhaps extreme sports, etc. Hope this helps!

  10. I almost wish I had this problem.

    I’ve always been the ugly duckling and I’m 36, at least that’s how I see myself. My fiancé says I’m pretty or beautiful, but inwardly I don’t believe it. I’ve always been overweight even though I’ve lost like 120 pounds. I have more to go. While I’ve never had someone so freaked to lose me, I’ve been cheated on a lot. I’ve been a hook up. Been teased mercilessly for being ugly.

    Both are difficult situations and it hurts self esteem. It’s insane.

  11. I had this problem. The insecurity of these guys is absolutely astounding, but they are weeding themselves out as both insecure (do you really want to tip toe around someone’s insecurities the rest of your life?) and a bit misogynistic for viewing you as object that is “out of their league” instead of a human with feelings. Consider it a blessing in disguise.
    All I can say is that at age 32, I married my bff and husband. We’ve known each other since 7th grade. He felt safe to me.
    This is why “pretty privilege” is a myth. Everyone has privileges and everyone has problems. You e done an amazing job of explaining it here.

  12. If so many people are saying that, even friends you trust, you start believing it too? It seems like you have self-esteem issues because of your history (I have a similar history and still working through it, so I’m assuming it’s somewhat close, but I apologize if it’s not). It’s a thin line between self-confidence and overconfidence 😅

    Either way, don’t try to settle for anyone just because. Have fun, keep meeting new people, and hope for the best.

  13. It’s way likely that it’s the type of guy you’re going after….. but also I need a picture lol

  14. I did something similar as a man. High school me was 120lbs at 6’3″, fucked up teeth, absolutely poor style(nothing fit right), glasses, head too big for my body, the works. I was very aware of these things so my confidence was subpar. I was invisible aside from my couple good buddies.

    I figured out eating more than once a day even if my body didn’t want to and got into the gym, 135lbs at the start to 225 closer to the peak. I got contacts and finally could afford Invisalign a couple years ago. I learned a few things:

    1)I am worthy of love regardless of what I look like
    2)Pretty privilege is revolutionary for self confidence
    3)women value potential partners based on who they are, but what you look like gets your foot in the door

    You’re going to have to meet these people in person, and you’re going to have to initiate. Most halfway decent men will not approach you because we assume, unfortunately based on experience, you are approached plenty and would prefer not to sacrifice our self worth “competing”. You’re gonna have to go about it like a man and lead with your vibe, in person.

  15. You keep dating these guys because they are gonna be bending over backwards for you.

    I only date girls i think are too good for me, if not i wont care enough to treat them right lol

  16. What a strange quandary to have. I too was seriously unattractive when younger, but it took me until 30 to be tolerable. Still think I’m hideous most days, but that’s psychological.

    I think maybe you pick men that are insecure like yourself because you can relate to them. If you date men with healthy confidence, it could turn out better in the long run. That also means you need to build on the love you have for yourself – and I know that isn’t easy.

  17. I read your other posts and I think the issue is that your self esteem is tied to your appearance. You’re probably not conscious of this but you’re picking guys who you’re settling for because you don’t think you’re good enough for someone better. You like that these men look up to you and think you’re attractive, even though it makes you uncomfortable, because it’s better than the alternative, where you’d have to deal with rejection for your appearance. Your boyfriend who you posted about before didn’t treat you very well and didn’t seem to respect you as a person very much, but clearly liked how you look. You’re dating these men because they like how you look. You’re dating these men because they validate you as a beautiful woman. But you’re unhappy because they don’t see you past that for who you truly are. You want more but you’re stuck in the same old patterns you’re used to because you’re afraid to step out of your comfort zone. You’re more concerned about whether or not these men like you than whether or not you like them.

    The trick is honestly to be more selective and stop settling for men who somewhat meet your standards and start dating men who you genuinely want to be with. Who respect you as a person and care about you beyond your appearance. The minute a man says “you’re too good for me” or makes a comment in line with what you’ve been experiencing, leave. Men should not put you on a pedestal for being beautiful. You’re more than just your appearance. They’re telling you how they see you and how they’re going to treat you. You’re not doing yourself any favors by dating men who view women as a status symbol or as something to be attained. If you can’t find a man who excites you, respects you, and values you as a whole person, you’re better off single.

  18. Have higher standards? All those people are probably right. Aim higher. It’s ok! You deserve it 🙂

  19. If you had early experiences in life that caused you to have an avoidant attachment style, it is likely that you will find anxiously attached individuals interested in you. [Here is a link](http://web-research-design.net/cgi-bin/crq/crq.pl) to find out your attachment style. Anxiously attached individuals can have difficulty with their self-worth and it can become magnified if you are very avoidant. A fearful avoidant can also cause extreme feelings in someone anxiously attached, due to the constantly conflicting messages that are being sent.

  20. It occurs to me your insecurities about yourself may have lied you to a pattern of seeking men with insecurities about themselves. Which might have been successful in a codependent kind of way if your looks matched your insecurities. But with your looks now giving off a different message, insecure men feel constantly inadequate.
    You’d have to find a self-assured partner. But I’m concerned that you’d be very much at risk of ending up with a narcissist who delights in the combination of good looks and lack of self-assurance, and would treat you badly.
    I strongly encourage you to find a good therapist and, separately, a good dating coach.

  21. Meh, I wouldn’t really worry too much about it. You’ll be ugly as shit again in just a few years.

  22. You Sound like you should date me don’t worry I’ll gaslight you into thinking you’re barely good enough for me and should be happy there is anyone that even likes you. Every mistake is your fault but occasionally I’ll tell you I love you and buy you flowers from the gas station. We’ll have 3 kids and a dog.

  23. from a fellow ugly duckling (magnet kid in elementary, was in every book fandom, went to a diff high school so i didn’t know anyone, glowed up end of senior year), i’ve had ppl tell me the issue is that i date “below me” bc i don’t think i deserve better. like that i’m used to being lowkey ugly and awkward and weird, so even though i’m not like that anymore, i feel like i am. maybe you’re dealing with the same thing.

    confidence is key! ppl are so attracted to confidence it’s insane. keep yourself open to opportunities, new ppl, etc. don’t just stick to dating apps

    shooting secure guy vibes your way

  24. Hey, I’m so glad you shared your story. I’m 18m, and I’m in college. Can I just say that I relate to MOST of what you said, about your transformation journey? I’m so happy rn.
    I hope you find what you’re looking for.😊

  25. Sounds like you’ve just been dating a bunch of insecure boys that don’t think they deserve anything. I used to be like that too, but that all changes once you start to love yourself.

    You’ll find someone who feels they deserve to have you in their life

  26. I feel like I’m not good enough. The men I’m attracted to generally aren’t interested in me and vice versa.

    I had a FWB and I hoped he’d give me a chance when he was ready to date again, but instead he started dating somebody else and I haven’t seen him since January. He knew my biggest fear was him disappearing and abandoning me entirely, yet he did it anyway.

    I hope you find a good man to be your Boyfriend someday!

  27. Only thing I have to add is to be careful of players.

    You’ve been dealing with a lot of insecure guys, its only natural now to rubber band a bit and be interested in guys who are comfortable and confident.

    Now, obviously, you should be looking for that

    But players can and will take advantage of your situation and expectations.

    Always gotta be careful with a guy that’s TOO smooth a talker lol

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