Just another agreement with ZipperJJ. And another plea to consider not going out with this woman. I’m starting to feel very bad for her and I don’t even know her.
You’re right. The answer to your question is “you can’t broach this without offending her”. Telling her she would just be sooo adorable if she would just do something with her face, just wouldn’t fly.
I met my husband in grad school where wearing makeup was the exception, not the norm. In fact, we were always a little suspect of women who were “too made up” as not being serious. (Of course, now that I’ve grown up 
I realize that was asinine too!). So, I’ve known plenty of women who are perfectly happy not made up and plenty of guys who don’t give a damn. In other words, she knows she doesn’t wear make up and is perfectly happy. One person’s unusual (she didn’t wear make up to a singles event???) is another person’s perfectly normal.
Don’t believe all the commercials, also.
I absolutely agree. This woman is not attractive to you, and that should be the end of the story - no harm, no foul. It sounds like you have decided not to ask her to wear makeup, and I agree with that, too - she’s in her 30’s, she’s an adult woman; she would wear make up if she felt like wearing make up.
Why would you say that? I’m just trying to defend my position. I’m not out to hurt people. I’m really very harmless.
Intentions don’t matter–
If you were to go up to her and suggest she need make up to be cute to you, could be hurtful.
Going out with her multiples times when she may be growing attracted to you while you were just wishing she would do something with her face could be hurtful.
Defending yourself, rather than trying to picture the situation from her point of view is exactly the problem. YMMV
deanc2000, your own preferences are your own. If you like your women shaved, plucked, painted, dyed purple, or wearing feather boas, that’s your call and no amount of people calling you shallow on an Internet message board is going to change what you like. If you’re sufficiently intrigued to give it another go, do so. There may have been some specific situation that led her to not wear makeup on that occasion and on your second meeting you might be pleasantly surprised by her dressing up a bit more. Or, you may find that her other qualities make her more attractive to you. Or you may just decide you aren’t compatible.
If you’re not sufficiently intrigued to risk it, then don’t. No worries.
I’m a woman who doesn’t often wear makeup and I’ve had a few entertaining and flirtatious chats with men that never went anywhere. Was it because I wasn’t wearing makeup? My clothes? Was I not as charming as I thought? Does he only like submissive blonde Asian women who are fluent in German? No idea, but there’s no horrific trauma in the fact that you will not be instant soul mates with every person you have a nice conversation with. At some point in adulthood, we must accept that others may not be as impressed with us as we are.
If you gave it one more shot and went out with her to see if her personality made her more attractive, or if she made herself up to your satisfaction, and then decided you didn’t want to go out with her again, that would not be the end of the world. It would not be a supremely dickish move. It would not mean you are a shallow oaf who is abusing delicate flowers of womanhood. It’s just part of dating.
Asking someone out isn’t a contract requiring you to adore every part of her and never, ever, ever let her down.
Exactly. The end of the story.
What she said.
It isn’t even about her face anymore, if it ever was. It’s about the fact that you don’t seem to care about how she might feel. You’re already in the middle of the dilemma of whether you want to try to change her or leave her. Since you can’t change her, I’d suggest leaving. And sooner is better than later for her sake.
I’m still siding with the OP. He seems willing to venture into the situation, saying “OK, not my cup of tea physically.” Many women seem to be haunted by the question, “Am I pretty?” But this is a woman who is already not striving to be so. I completely understand those who feel that if the physical attraction isn’t there, don’t go there…but by virtue of the facts that she puts herself out there, unadorned, and he is willing to try, I say let him try.
There really are many things in life more important than physical perfection. I have a feeling other posters want to spare her the hurt, but I don’t think it’s going to go that way. The woman in question is willing to suffer some false negatives in hopes that when it’s positive, it’s really positive. C’mon it’s a date, not Armageddon.
This. Mrs P hardly ever wears make up. She certainly never wore it when we were dating.
Any suggestion that she just forgot that day or something is silly beyond words. If it’s not a medical reason, she has made a very deliberate choice. If she’s anything like Mrs P, it will be a choice quite central to her personality as a whole.
You need to decide if you like this now. If not, forget it. Going by the OP, indeed going by the fact you even posting this, I’m guessing “forget it” is the appropriate choice.
That’s how I feel as well.
Look, the guy obviously recognizes these woman’s positive qualities. He just wishes that the woman looked better, and I’m sure that we’ve all thought that way about a prospective romantic partner on occasion. He’s willing to give the relationship a shot, and more power to him.
Because she’s not wearing make up, she’s not striving to be pretty? There are a plethora of reasons why she might not be wearing it, and may still feel that she is striving to be her prettiest. Maybe SHE thinks she looks better without it. And hell, maybe she does. She certainly has more information than the OP on that score.
As a woman who does not wear make up except to very big events, I’d say that if a guy asked me to start wearing make up so that I’d look pretty enough for him to date, I’d laugh in his face and that would be the end of that.
OMG, you and the other one haven’t even read my previous posts. I’VE BEEN IN HER SHOES MANY TIMES! I’ve been rejected for superficial reasons so I know how it feels. IT SUCKS.
What do you mean it’s not about her face anymore? You don’t give any reasons to support your assertions. How do you know I don’t care about her feelings? Did I say or suggest that I didn’t? Of course, I am aware of her feelings and her POV.
I’ve read all of your previous posts in this thread.
You’re 5’7’’ tall and pretty sensitive about that. If a woman was on a public message board asking how she could ask you to wear elevator shoes whenever you were out in public with her, what would be your thoughts about that?
I guess what I meant was that this thing about her face is so central to you that it’s not really about that anymore. If this is the thing that tips the balance, it’s probably lots of other things that didn’t overwhelm you.
If that’s true, it’s not evident from this thread.
Before I got a chance to reply, you edited out that you agreed that sooner was better than later. Did you take that out because you changed your mind and no longer agree? Or some other reason?
If you know that it sucks to be rejected for superficial reasons, might it not be nicer to let someone go before they have to know that it was for superficial reasons that they were rejected? At this point, a simple. . .not my type would suffice to move on and not get anyone hurt.
Wowsers, deanc2000, you’re really getting the gears in this thread.
Personally, I don’t see much wrong with your OP - you met a woman who you like but don’t find pretty - that’s a drag.
However, her other qualities are positive enough that you want to go out with her again. Cool.
Personally, I think you should go out with her on a date and see what happens. Maybe she’ll show up with makeup and you’ll find her a total bore. Maybe she’ll have no makeup but be more rested or laugh at all your jokes and get a really pretty flush to her and you’ll suddenly think she’s a goddess. Maybe you’ll see her and she still won’t be pretty, and you’ll still like her and you’ll decide exactly how much non-pretty you can put up with.
I don’t know and neither do you. I think you should take her to a nice dinner. Dress up nicely, tell your best jokes, charm her to bits and see what happens.
I’ve heard more than one man say that having a woman glowing and laughing at his jokes, hanging on his every word, makes her very beautiful even if she does have a big nose, or small eyes, or thin lips.
I agree with every word of this.
I feel like I’m living in an alternate universe. I’ve never had a man or woman I was dating make any negative comment about my body or imply anything was unsatisfactory about my appearance. That includes hair length and style, makeup or lack of makeup, and any sort of shaving or not shaving. My reality is that I don’t think about any of that very much. I wouldn’t be interested in dating someone for whom something like that was a problem. YMMV, but this has just never been an area of focus for me or my sweeties.
OK dude. You didn’t read my post when I wrote that I wouldn’t lead her on longer than necessary? That’s why I erased the other phrase, because I’D ALREADY WRITTEN IT! You’ve already made your judgement about me, dude, you’ve jumped to a conclusion and anything I say won’t budge it.
Didn’t I also write previously that she had other qualities that were attractive, including her personality? Why then would you say that I’m “centered” on her face?
Yes, it’s the one characteristic about her that one could say is a flaw, and I’m trying to come to grips with it. But I am still keeping in mind her other qualities.
Please Open up your mind to the possibility that people are not all good or bad, there are shades of grey mostly, I’m definitely not a Saint, but also I’m not the epitome of evil. I would love to say that I was alright with dating a girl who was a great girl in every respect other than being plain, but it’s not so easy for me right now. I JUST MET HER! Is that so hard to accept in your mind?
Not the hurt so much as the bother.
She’s a grown up - this isn’t going to devastate her. But time spent with someone who is trying to figure out if he’s only sort of unattracted to you or really unattracted to you is time better spent watching paint dry. Do her the favor of freeing her up to do something worthwhile.
The issue isn’t that you met a plain girl and don’t know if you want to date her–that would be a very different thread. The issue is that you seemed to think (and you haven’t explicitly changed your position on this, as far as I can tell) that it might be appropriate to ask her to change, that you could educate her on her deficiencies. That’s what has people upset–the implication that maybe she just doesn’t realize she’s plain and needs to be told. She knows. She choses otherwise. To bring it up to her would be so socially clueless and painful to her that it is bothering people that you’d even consider it, I think.