Dating a Woman Way Out of My League. How Do I Not Mess This Up? - /adv/ (#33203159) [Archived: 1733 hours ago]

Anonymous
6/11/2025, 4:04:44 PM No.33203159
HD-wallpaper-bogdana-beautiful-beauty-blue-eyes-cute-dark-hair-eyeglasses-portrait-pretty-russian-thumbnail
Was 19 when we met. Pretty average guy, maybe a 6.5 on a good day but a little taller than the average. Two of my friends started dating girls from the same group, and I got paired off with the quiet, chubby one. She was shy, always in hoodies, soft-spoken. We started talking, got close, and ended up dating.

She was incredibly sweet and loyal. No drama, no stress, just comfort. The only issue was she hated the gym and felt insecure in tight clothes. She never really wanted to change, and I stopped asking. We dated for three years through college. After graduation, I moved out of state for work, and we broke up peacefully.Now I’m 27. One of my friends got married to her best friend, and I was the best man. I knew she’d be there, but I wasn’t prepared.

She walked in and looked completely different. Lost around 50 pounds, confident, glowing, wearing a tight dress that showed off her figure. Honestly, she looked stunning totally out of my league.

She came straight up to me and said, “You look really handsome.” We talked all night. Same sweet voice, but more confident. She told me I always made her feel safe. We ended up sleeping together.We started talking again, dated long-distance for four months, and now she’s moved to my city. We live together now for about 5 months.

I’m happy, but I’m also insecure. She’s way out of my league now. People stare when we’re out. I keep wondering why she chose me. Am I enough?

I love her. I want this to work. But I don’t know how to stop feeling like I’m not good enough. Any advice?
Replies: >>33203185 >>33203335 >>33203397 >>33204563 >>33205298 >>33205802 >>33206862 >>33207008 >>33207332 >>33213142
Anonymous
6/11/2025, 4:14:00 PM No.33203185
>>33203159 (OP)
>Chubby
How chubby are we talking about?
Replies: >>33203189
Anonymous
6/11/2025, 4:15:39 PM No.33203189
>>33203185
She ha BMI of 32. But had a cute face and was pretty submissiv in college, she would let me do everything with her.
Replies: >>33203209 >>33205361
Anonymous
6/11/2025, 4:21:51 PM No.33203209
>>33203189
>32 Bmi
That's not chubby. That's obese.
Anonymous
6/11/2025, 4:53:08 PM No.33203335
>>33203159 (OP)
girls love to feel safe next to someone
they'll always go back to the man that makes her laugh and feel safe and fucked her good, don't worry about how you currently look or your money or anything
obviously don't let yourself go but if she's there right now she has her reasons beyond looks, a lot of girls are like that, looks come second after some other thing
something a lot of people around here will have a hard time accepting
(not to mean a 10/!0 will date a 2/10 but if you're around the same ballpark the looks come second for a girl)
Replies: >>33203560
Anonymous
6/11/2025, 5:17:54 PM No.33203397
>>33203159 (OP)
She chose you. She likes you. Show her the respect of assuming she knows what she wants
Replies: >>33203584
Anonymous
6/11/2025, 5:53:12 PM No.33203560
>>33203335
She told me she feels like she can truly be herself when she’s with me. That she can sit in silence without feeling judged, that she doesn’t have to hide her excess skin, and that when she’s feeling down, being around me always lifts her up. She even said I always made her feel like the most beautiful woman in the world, even when she was at her heaviest.

It’s not that she’s ever done anything to make me feel insecure. It’s just that when we’re out together, guys still hit on her, even while we’re holding hands.

One time, we were at a restaurant, and this good-looking waiter actually slipped her a piece of paper with his Snapchat on it. It said something like, “Hit me up after you dump this loser.”
Replies: >>33203592
Anonymous
6/11/2025, 5:58:21 PM No.33203584
>>33203397
You’re right. I know she chose me, and I know how much that means. I love her deeply, and if I hadn’t moved states, I never would’ve broken up with her. I’m actually planning to propose. It’s just that sometimes, when we’re out and I see the way people look at her, I get in my own head and start feeling like she’s too good for me.
Anonymous
6/11/2025, 5:59:55 PM No.33203592
>>33203560
lol
well if a girl did that in front of your gf you'd say something right
I would, I remember a girl hitting me up in front of an ex and telling her to have some dignity and respect and to stop doing that etc
my ex fucked me like a maniac that night
does she say something when other men hit her up?
she might feel too starved of attention because she was fat a lot of time and now she's getting all the attention but still, she should know better than not do anything if other men hit on her in front of you.
Replies: >>33203707 >>33203740
Anonymous
6/11/2025, 6:23:44 PM No.33203707
>>33203592
He slipped her the paper while I was in the bathroom. When I came back and sat down, she showed it to me and told me he’d given it to her while cleaning the table next to ours. She said if I even tipped him a cent, she wouldn’t talk to me. She was pretty angry, it felt to her like he was calling her a slut who sleeps with anyone.

Later, when we got home, we had crazy sex. She wore some sexy lingerie and made me fuck her without a condom.
Replies: >>33203898
Anonymous
6/11/2025, 6:31:12 PM No.33203740
>>33203592
>does she say something when other men hit her up?
When we go out together, whether it’s for drinks, the park, or somewhere else, she likes to dress up and wear bright, pretty colors, but she really hates it when guys try to talk to her.

When she’s out alone, she usually keeps it simple, dresses more conservatively, and doesn’t wear much makeup.
Anonymous
6/11/2025, 7:00:48 PM No.33203898
>>33203707
Lost a great opportunity there, should've tipped him 1 cent and said "This is for how much you're worth, better luck next time, loser" and walk it off confidently. You should always act like you're better than everyone else and be confident. If you start showing other guys can are better than you and you are insecure that others will take her from you then you'll come off as weak and she'll lose respect.
Replies: >>33204060
Anonymous
6/11/2025, 7:33:23 PM No.33204060
>>33203898
It’s not like I show how insecure I am. I get that no one wants to constantly reassure their partner that they love them and there’s nothing to worry about. I really try not to let it show. Even that day with the waiter, I just brushed it off and made a small joke about the whole thing
Replies: >>33204235
Anonymous
6/11/2025, 8:14:44 PM No.33204235
>>33204060
Then you got nothing to worry about. The only advice I can give is to keep working on yourself and improving everyday, bodywise, mentalwise and moneywise. If she likes you the way you are, improving yourself will keep that and eventually you'll stop feeling like you're not enough. If you let yourself go because of these thoughts on the other hand...
Replies: >>33204272
Anonymous
6/11/2025, 8:27:07 PM No.33204272
>>33204235
Yeah, you’re right. I’ve actually come a long way already. When we first started dating and were living three states apart, I was really insecure. I used to call and text her constantly. After a while, I realized I was probably coming off as controlling and immature, so I started working on it little by little.

I still have moments where I feel like I’m not enough, but I’m doing my best to keep improving. I make about 75k after taxes, I take care of my body, and I go to the gym at least three times a week. She goes to dance class once or twice a week and joins me at the gym at least once.

We’re even building a home gym together. She doesn’t really like public gyms because she feels like people are always staring at her.
So yeah, I’m sticking to the path. Just doing my best to keep growing every day, like you said.
Anonymous
6/11/2025, 9:28:41 PM No.33204563
>>33203159 (OP)
Put the effort in and get jacked, she obviously likes you enough to go back even after her glow up, if you have your own it's only going to help you and show you're also willing to put in the work.
Anonymous
6/12/2025, 12:17:54 AM No.33205298
>>33203159 (OP)
Because you pair bonded with her. Some people are more sensitive to oxytocin than others. You probably look way more handsome in her eyes than you do to yourself in the mirror so what is there to worry about?
Replies: >>33205337
Anonymous
6/12/2025, 12:26:57 AM No.33205337
>>33205298
>more sensitive to oxytocin
Honestly, I never thought that. It's just like pic related seeing with an average dude. You would probably think why that hot woman is together with that ugly looking dude. Im probably just overthinking things, but yeah, im not doing anything to destroy this relationship, im actually planning to propose to her next month
Anonymous
6/12/2025, 12:31:53 AM No.33205361
>>33203189
>She ha BMI of 32. But had a cute face and was pretty submissiv in college, she would let me do everything with her.
You have nothing to worry about

She knows you liked her as a porker unless you catastrophically fuck this up that's loyalty you can't buy. She will always give you the benefit of the doubt because she knows you aren't there for her looks and she can't guarantee that with any other guy (because they'll only have known her skinny)

Just fucking coast man. You bought MSFT at IPO
Replies: >>33206841
Anonymous
6/12/2025, 1:31:51 AM No.33205645
>Luckiest guy in the world has a guaranteed relationship in the bag and is wondering how to not mess it up
kys
Replies: >>33205707 >>33206834
Anonymous
6/12/2025, 1:46:41 AM No.33205707
>>33205645
Seems pretty reasonable. He more or less won the lottery. I'd be scared of fucking it up too if i were him.
Replies: >>33206834 >>33212809
Anonymous
6/12/2025, 2:14:54 AM No.33205802
>>33203159 (OP)
Repeat after me: "It's just a woman, nothing special."
Anonymous
6/12/2025, 7:17:41 AM No.33206834
>>33205707
>He more or less won the lottery. I'd be scared of fucking it up too if i were him.
Pretty much this.
>>33205645
Think about it you dated a girl for 3 years break up, and years later, you meet again. The chubby girl now looks like a super model, and what's more surprising she wants you. You would probably be scared as well because he really just wo. In life, like a dude who bought Bitcoin 10 years ago. He should just relax and marry that girl because this is 1 in a lifetime opertunety
Replies: >>33212809
Anonymous
6/12/2025, 7:20:45 AM No.33206841
>>33205361
Right? He dated her for 3 years while she was chubby. She knows that you actually love everything about her, not just her body.
Anonymous
6/12/2025, 7:25:33 AM No.33206862
>>33203159 (OP)
Dude, just marry her. She loves you more than you can imagine. Plus, you were with her for three years when she was at her heaviest, she knows you love her for who she was, not just who she’s become. I’m pretty sure she wants to spend the rest of her life with you. So take the chance and propose.
Anonymous
6/12/2025, 8:41:43 AM No.33207008
>>33203159 (OP)
Use this feeling of unworthy-ness to make yourself a man you think can stand shoulder to shoulder with her. Work on your appearance, your skills, your career etc. treat her well but do not put her in a pedestal.
Anonymous
6/12/2025, 11:31:10 AM No.33207332
>>33203159 (OP)
Had this in high-school I'm an ugly dude now fat but in high school I dated the prom queen.
I was a gymnast and my face is terrible but my body use to be perfection.
I was popular too.
Going out was bad I'm short and with clothes on I didn't look like much.
Guys use to hit on her with me there all the time.
I got into fights too I could take your head off with a kick back in the day.
That's why she left me actually
Replies: >>33207781
Anonymous
6/12/2025, 2:27:55 PM No.33207781
>>33207332
Well, I don’t get into fights, and she also loves my muscles. Sometimes when we’re lying on the bed, she’ll kiss my abs and tell me how much she likes my strong arms.
Anonymous
6/12/2025, 8:31:52 PM No.33209312
Nice hamplanet you got there son
Anonymous
6/13/2025, 1:10:28 PM No.33212809
>>33205707
>>33206834
That's the thing, there is zero way he can mess this up.
Anonymous
6/13/2025, 3:21:06 PM No.33213142
>>33203159 (OP)
>Was 19 when we met.
>Now I’m 27
bro she's settling for you because she's pushing 30. date a younger women in her prime. maybe date this 27 year old bur look for someone better
Replies: >>33213940
Anonymous
6/13/2025, 6:20:36 PM No.33213940
>>33213142
Dude if she looks anything like that pic it doesn't matter, she would be able to get any guy she wants. She is with him because he was there when she was fat and both hit it off while she was at her worst. He can't mess this up, he should just marry her and put a child or two in her