How do you date a woman who is better looking than you?

[ironpony]

There is a co-worker of mine and normally I don't like to date co-workers but she send me messages on facebook that seems like flirting and she seems like she is interested in me.  I showed them to my friends to get their opinion and they said she is totally flirting and giving me hints.

However, I feel looks wise, that she is way out of my league and she is also thinner than me too.  I feel self-conscious about my weight when around her and almost my age, cause she seems like she is at least 10 years younger than me, but can only guess.

So I feel that I am out of her league, looks wise, but I think she's really cool and funny in personality and really goodlooking, so I feel I should ask her out but wonder if she is going to have second thoughts if sees the clothes come off down the road, weight wise.  What do you think or how should I handle that?  Thanks for any advice on it!  I really appreciate it!

[ExpatInItaly]

17 minutes ago, ironpony said:

she is also thinner than me too.  I feel self-conscious about my weight

As a woman, I can tell you that most women would not have a problem being thinner than their man, OP. Quite the opposite. 

If she's flirting with you, it is safe to say she is attracted to you, and you are over-thinking due to your own insecurities. She already clearly knows what you look like and has probably already imagined what you might look like undressed. She apparently likes what she sees and what she imagines, or she would not be dropping hints like this.

Ask her out and take it from there, man. 

[Wiseman2]

1 hour ago, ironpony said:

 I don't like to date co-workers .

Agree. Best not to get involved with coworkers.

It's also not a good idea to share anyone's private communication with your friends for a survey.

[Blind-Sided]

As above... it's not good to date co-workers.  If it ends bad... you may be looking for another job.

But, as also said... girls don't always go purely for looks.  And to a guy... you can't judge yourself.  I'm a little over weight... have gone bald... gray... and am late 40's.  After my D... I attracted several girls who just saw a "confident, handsome guy."  To an "Adult" woman... there is more to attraction than being good looking , or having 6 pack abs.

[elaine567]

2 hours ago, Wiseman2 said:

Agree. Best not to get involved with coworkers. ✔️

It's also not a good idea to share anyone's private communication with your friends for a survey. ✔️

 

[Gaeta]

Don't date her.

You will always feel you're not worthy, always wonder if she'll move on with someone better looking, always wonder what she sees in you.

 

[ShyViolet]

If she's sending you flirty messages then that shows she is interested in you.  There's no need for you to overthink whether she's out of your league.  You literally have nothing to lose if you just give it a shot.  Some women don't place looks at the top of the priority list; I've dated a lot of guys who really weren't conventionally attractive, because they had other qualities that I liked, and I have really never been the type of woman who goes for the male-model ""Brad Pitt" type.  As a matter of fact I wouldn't want to date someone who looked like that.

[Uruktopi]

Women´s "criteria" to find a man to be attractive are (or may be), life be blessed, quite different than men´s (our) ones.

Well, at least is what makes the difference between girls and grown up women.

Not necesarily the same way, vive la différence! , we men, also mature.

Live and learn.

[Johnjohnson2017]

Some women put more emphasis on personality than looks. If she is contacting you, it means she isn't creeped out by you. She finds you cute enough to be attracted to you.

Keep communicating with her and getting to know her. you don't have to ask her out right away. is she single? recently out of a relationship? Take your time getting to know her a little better.

[smackie9]

Nothing unusual about women going for someone that is less attractive. Women think with their emotions, so there is something about you she finds appealing. I myself have dated a variety of men, short,fat skinny,tall, really attractive, and unattractive.

A co worker of mine, who is beautiful, only dates older guys that are big and hairy. In fact there's a few coworkers of mine that would take big and hairy over young and fit. So I wouldn't over think this at all.

[Fletch Lives]

Start working out.

[Ami1uwant]

4 hours ago, Gaeta said:

Don't date her.

You will always feel you're not worthy, always wonder if she'll move on with someone better looking, always wonder what she sees in you.

 

This can happen in any relationship if there is a perceived difference such as looks, money, personality, age, etc.

[central]

Dating a coworker is usually a bad idea.  She may seem out of your league, but that doesn't matter if she's interested.  Besides, in 20 years, you may look better than her!

[Trail Blazer]

Dating a woman more attractive than you is easy.  If she's dating you it's because she likes you.  Many women aren't as looks-focused as men are, so stop thinking about it through the male frame of mind.

On the other hand, dating a woman who is also a co-worker is a much riskier proposition.  Let's face it, most relationships don't last.  You have to ask yourself whether or not thr fallout from this relationship failing would be worth the risk?

[ironpony]

Oh okay thanks.  All good points, thanks.  Well as far as dating a co-worker goes for being a bad idea, it's just that it's been really hard meeting women because of covid and people just don't go out anymore in big social events, so I feel that since this women keeps to talking me and giving me hints that maybe it's a sign.

Plus my boss at work is romantically involved with one of the other workers, so I thought maybe he would understand in his position, if he were to find out.

[norealusername]

From what I've seen, most women don't care about your physique. They like a tall big guy, doesn't matter if he's overweight and in poor physical condition.

[ironpony]

Oh okay, I will keep these things in mind.  Good points.  Well she asked me out and I couldn't help to say yes, so I guess that's that...

[Blind-Sided]

9 hours ago, ironpony said:

Plus my boss at work is romantically involved with one of the other workers, so I thought maybe he would understand in his position, if he were to find out.

Doesn't make it right.  

It could be fine.  If you have a long relationship... it's never an issue.  But if it's an ugly break up... then you can't work together.

[HiCrunchy]

In most couples, I feel like the woman tends to be the "prettier" one, in the realtionship

 

[BeanCounter]

17 minutes ago, HiCrunchy said:

In most couples, I feel like the woman tends to be the "prettier" one, in the realtionship

 

This is a point I was going to bring up. I honestly feel like there are simply a higher amount of attractive women on average than attractive men. It's likely because of the amount of pressure put on women to be pretty over centuries. Those pressures are slowly starting to change, but we are talking about a LOT of history here.

Aside from that, the whole "work relationship" thing is very relative. I know plenty of people who met their spouses at work. It's like someone else said - you've got to weigh the risk vs the reward, and understand it could end poorly and you could be forced to see this person daily after it ends poorly. We also don't have a lot of information here - is the person in an entirely different department than you? That's a big difference than if they are on your direct team or something.

Regarding the feeling she is more attractive than you, I think you've got to push that out of your mind and be confident. As a guy with a few extra pounds, you've got to look at the other qualities that you have that did attract this girl and remember those. For me, I think it's my smile and my genuine personality. I try to focus on those things and have fun when on dates. When the clothes come off, just be confident - things aren't going to be a total shock, your body is your body. And women, even very pretty ones, are very often just as insecure with their bodies as you are.

Best of luck on the date, make sure to give us an update

[ironpony]

Oh okay thanks for the information.  Well we hardly ever see each other at work, since she works on a different side of the building and she works the earlier shift and I work the late one.  We bumped into each other a couple of times, but it isn't much.

 

33 minutes ago, BeanCounter said:

This is a point I was going to bring up. I honestly feel like there are simply a higher amount of attractive women on average than attractive men. It's likely because of the amount of pressure put on women to be pretty over centuries. Those pressures are slowly starting to change, but we are talking about a LOT of history here.

Aside from that, the whole "work relationship" thing is very relative. I know plenty of people who met their spouses at work. It's like someone else said - you've got to weigh the risk vs the reward, and understand it could end poorly and you could be forced to see this person daily after it ends poorly. We also don't have a lot of information here - is the person in an entirely different department than you? That's a big difference than if they are on your direct team or something.

Regarding the feeling she is more attractive than you, I think you've got to push that out of your mind and be confident. As a guy with a few extra pounds, you've got to look at the other qualities that you have that did attract this girl and remember those. For me, I think it's my smile and my genuine personality. I try to focus on those things and have fun when on dates. When the clothes come off, just be confident - things aren't going to be a total shock, your body is your body. And women, even very pretty ones, are very often just as insecure with their bodies as you are.

Best of luck on the date, make sure to give us an update

This is the thing though, is that I do not know of what other good qualities I have per se.  I am autistic and still live with my parents right now, because I haven't decided on certain things yet in life, and was told I couldn't make it on my own, so I feel intimidated in my personality qualities as well.

I've had gfs before but that was when I was younger and perhaps it was more acceptable to not live on my own yet.  Plus those gfs were not near as goodlooking as this woman and not the type to do the persuing work themselves as much like this woman is.

Edited June 21, 2021 by ironpony

[Mrin]

There is a song by Dr. Hook on this... "When you're in love with a beautiful woman"

[BeanCounter]

1 minute ago, ironpony said:

Oh okay thanks for the information.  Well we hardly ever see each other at work, since she works on a different side of the building and she works the earlier shift and I work the late one.  We bumped into each other a couple of times, but it isn't much.

 

This is the thing though, is that I do not know of what other good qualities I have per se.  I am autistic and still live with my parents right now, because I haven't decided on certain things yet in life, and was told I couldn't make it on my own, so I feel intimidated in my personality qualities as well.

That's a good thing probably! I think the whole "don't date someone you work with" statement really applies more so to someone you're going to have contact with every single day at work. This person is clearly not that, so in my opinion, you're fine to give it a try.

Regarding your good qualities, you're still only focusing on things that you perceive as negative, or things that you're worried that someone else is going to perceive as negative. I wouldn't advertise something like living at home still, but if it comes up, drop it confidently and do not be embarrassed by it. Autism I can't specifically speak to, but does she know this about you? Being autistic can mean a LOT of different things, but I think the connotations of the word has changed so much in the past decade...

Like other people said, this girl sees something she likes in you! Negative energy is something that can be sensed, don't carry it with you on a date. 

What did you decide to do as a date with her?

[Gaeta]

Yes yes all this is true women don't only go for looks and are attacted to a 'combo' including personality, confidence,  etc. 

That being said, the issue here is not that she's out of OP's league. The issue is how it makes him feel. 

I've seen plenty of pretty ladies dating average men or less than average men but these men compensated by being confident, and felt pride in having such a lady in their life, not fear and uncertainties. 

Ironpony's  insecurity is in this situation is the issue and it's not going away because a few people told him 'go ahead date her'. 

[BeanCounter]

2 minutes ago, Gaeta said:

Yes yes all this is true women don't only go for looks and are attacted to a 'combo' including personality, confidence,  etc. 

That being said, the issue here is not that she's out of OP's league. The issue is how it makes him feel. 

I've seen plenty of pretty ladies dating average men or less than average men but these men compensated by being confident, and felt pride in having such a lady in their life, not fear and uncertainties. 

Ironpony's  insecurity is in this situation is the issue and it's not going away because a few people told him 'go ahead date her'. 

So then the suggestion is "don't date her" and basically do nothing? Not sure how you're supposed to gain confidence and experience if you don't take risks.