What’s this nonsense about giving her “one more chance”? You make it sound like she’s cheating on you by not wearing makeup. Maybe you need to grow up a bit and be a little less shallow?
I’m in the minority here, but I think you folks need to give the OP some benefit of the doubt.
Let’s face it, we ALL have physical preferences for mates. A man might really like tall, slim redheads - but might marry and be very happy with a short brunette, right? Now, if short brunette is willing to try dying her hair red that’s awful sweet of her, BUT we all agree that it must be HER choice (maybe she finds out her man is hot for redheads and she wants to do this for him, whatever). But if short brunette never wants to dye her hair, well, her husband might still have a long, loving marriage with her. It’s just that her other qualities outweigh the fact she’s not his physical ideal.
Sounds to me like the OP prefers women with a certain amount of make up (or at the least is accustomed to seeing this) but her lack of it is not a total deal killer - if it was, he wouldn’t be considering asking her out again. So, he has a preference, and it’s no more peculiar than liking red hair, women of a particular ethnicity, women in spike heels, or anything else of that nature. He is no more or less shallow than anyone else who has appearance preferences for a mate.
I can understand him wondering about asking her to wear make up, because it seems like an “easy fix” to make her more his ideal, but he knew it was minefield - that’s why he asked on a message board. The answer, of course, is no, it’s not appropriate to ask her to use make up, or why she doesn’t use make up.
Now, it’s up to him to decide just how important his physical preferences are for a mate. He might go out with her again, decide her other qualities outweigh this, and it could be a long and happy thing for everyone. He could go out with her again, decide her other qualities don’t outweigh all that, and end things amicably without ever bringing up the make up question. Or he could decide not to ask her out again.
Do you mean, “Dress up cause we’re going someplace nice.” or “Change your clothes, you look like slob”? Because they are 2 different situations. And if someone told me to change my hairstyle after a few dates, I would be really insulted.
In the early stages of a relationship, you probably shouldn’t be “suggesting” anything other than “You should really wear that color more often. It really brings out your eyes,” etc.
I think what people are telling you is there might be a time you could broach this, but that time, if it occurs, would be well after the time when you have to decide if this is a dealbreaker for you.
I think my kneejerk reaction is sparked partly by the title - you met a woman who wasn’t wearing makeup? Did you report her?
At a singles event, that’s unusual. I’m ruling in favor of the defendant. 
I wish I could find a video clip of the episode of “Herman’s Head” where he dates the woman who doesn’t shave her armpits. Anyway, here’s a clip with Megan Mullally (sp?).
Why did they ever cancel that show? And why isn’t it on DVD?
Understood. Maybe you can fight my ignorance on this: I assume that most women can wear some makeup. E.g. maybe she’s allergic to foundation, but she can wear mascara. I’m reading the OP like she’s not wearing one speck of makeup. How likely is it that she’s not wearing it because although she wants to, she can’t—ZERO mascara, lipstick, eyeliner, foundation, etc.? I assumed most women can wear at least some; I’m not saying they should, but rather, noting that I didn’t think it likely that this woman couldn’t wear any at all, i.e. it’s partly choice and not total necessity.
You point out that maybe she thinks she looks better without it, and that’s possible, as it is possible that she really does look better without it. It’s also possible that she might be one of those whose friends will send her to “What Not to Wear” for a makeover. Some of the women on that show really blossom—they never would have tried new clothes or a new approach to makeup if their friends hadn’t pushed them and they’re grateful for it.
I’m not saying everyone would be. Some would think, “Who are you to tell me that I’m not pretty enough or stylish enough or whatever enough?” Got it. But just as some love a surprise party, others might be mortified. But we wouldn’t ‘outlaw’ surprise parties as evil incarnate because for some people, they’re the best thing ever.
Obviously, I’m against OP recommending it to her. Others have bashed him for not accepting her as is, but I think that describes 99.9999999999% of relationships. We accept people without our sense of humor, whose interests are different than our own, who aren’t quite as tall (or short, me lurvs the petite ones) as we’d like, blah blah blah. There are no perfect matches—something’s always a little off with appearance or personality or income or intelligence or politics or whatever…but I’ll stop just short of 100% because maybe there truly is one out there somewhere.
Props to the OP for honesty and running it past others in hopes of avoiding the commission of a grave faux pas on another human being. I’m not surprised that makeup is a hot button issue for a lot of women.
I don’t want to leap in and make some sweeping generalization about women, but… I work in a school, and I’d say half wear make up every day and half wear none. There are varying degrees of make up, from just eye stuff to a full face. Some women who do not wear it to work would wear it for a date, or would not wear it for a date but would wear it for a wedding. It’s not just a “do you or don’t you” issue.
Me, personally, I don’t wear it unless it’s an event on the level of a wedding, and I’m really dressed up. It has never affected my ability to date, that I know of, and any guy who would have wanted me to wear make up regularly would have been disappointed. It’s just not going to happen.
And if it’s a conscious choice and not just momentary laziness, she’s even LESS likely to want to start doing it, especially for some guy she hardly knows. I don’t get why women are expected to make up their faces but men aren’t.
Sure, but my question is whether they can or not. By “can” I don’t mean “are allowed by the rules” but rather, that they would experience no ill side-effects, such as allergic reactions. I would guess lipstick is probably ok for a vast majority. The woman in question didn’t wear any.
There may be some women who wish they could find a product to even out their skin tone but it all makes them break out in a rash, so they content themselves with lipstick, mascara, or other things that they can wear without adverse health effects. But again, choosing is a different matter.
Me neither, but I’m glad I don’t have to. I do know that there are beauty contests for men elsewhere…
That sums me up, as well. I hate taking the time to fuss with it, and I’m just not going to do it on a regular basis. My social life never suffered for it, as far as I could tell, and my husband doesn’t care. I’m not saying he doesn’t appreciate it when we get dressed up to go out, and I put some on, but he doesn’t expect me to do it on a daily basis.
And it’s not a “hotbutton” issue for me. I never really think about it. I would hate to have to start thinking about it because some guy told me I’d be the perfect woman if I’d only put on some mascara.
Do people start threads when it’s just a bit of a preference? I can’t imagine starting a thread like this unless it was very important preference-wise.
I don’t wear makeup. I’m not going to start for anyone. Not only do I have severe allergies, I also find the very idea rather gross. I don’t like lotions or lip balms or stuff clinging to my face.
OP, this woman’s normal, natural face repels you. That’s all you need to know.
I’m still struggling with what appears to the OP’s desire to have an illusion rather than work with reality.
It’s kind of an offensive analogy but it works: You can put lipstick on a pig but it’s still a pig.
A plain-faced woman is still plain-faced, even if she puts makeup on to mask the plainness. A flat-chested woman is still flat even if she stuffs her wonder bra. A short man is still short even if he wear lifts. A bald man is still bald even if he wears a hair piece. An amputee is still an amputee even if he wears a prosthetic.
If you have a problem with this plain woman, then her wearing makeup is not going to take away that problem. That face you saw is her face. Unless you expect her to wear makeup 24/7 whenever you’re around, there’s no escaping that reality and eventually you’ll have to accept it. What are you going to do then?
I don’t think the OP’s shallow. I just think he’s deluding himself if he thinks her putting on a little rouge and powder is going to make everything hunkey dorey now. Perhaps if she had been wearing makeup when they first met, then her plain face wouldn’t be such a dilemma (maybe something else would have been…who knows?). But since she left the truth out before the rose-colored glasses of infactuation could set in, this might be too big of a hurdle for the OP to jump, IMO.
I agree with you on this point. I call it my “minimum standard of non-hideousness.” That verbiage is meant to be humorous, but I think we all have a minimum standard for looks, and that’s okay. Wanting to be with a person that you find attractive does not necessarily equal being overly picky or shallow.
BUT–Makeup WILL NOT change an unattractive face to an attractive face. Makeup may indeed make her look “better,” but it won’t change the basics.
Take me, for example. As far as I know, I’m generally considered “pretty.” And I do usually wear some makeup because I think it makes me look better. I’m one of those redheads with invisible eyelashes, so some liner and mascara does a lot of good. And in the last couple of years (I’m 37), I’ve noticed that a little undereye concealer goes a long way. Looking better makes me feel more confident. Doing my makeup takes about 3 minutes. For me, it’s a no-brainer. I’m wearing it.
But that said, there is no way that a man that finds who me attractive in makeup will find me unattractive without. My face is my face. My face with makeup is just my face, but slightly enhanced. If I put on a ton of the stuff, I’d just look like myself with a ton of makeup on.
So, dean, if you like the way women look with makeup on, that’s fine. But don’t think for a second that it will make any substantial difference in the way she looks.
Gah…ywtf snuck in on preview with the same point! (Nice username/subject match, by the way.) I was thinking of the “lipstick on a pig” analogy too, but forgot about it before I found a way to work it in. 
Whoa! I didn’t accuse you of being Jack-the-ripper. I just suggested that you not date this woman.
It seems that the way that someone looks is fairly important to you. And that’s fair. I’m just suggesting that you don’t “come to grips with it”. Since beauty is so subjective, I’m suggesting that you just move on and find someone who meets your standards.
I’ve had two different men tell me that their girlfriends were plain. I don’t think either of them ended up with those women. And I don’t think that’s because of the way the women looked. I saw them and they looked fine to me. But the fact that the men focused on that aspect didn’t bode well for the relationship. When you’re focusing on something like that, you’re basically saying that the whole package doesn’t fit you. I’m just suggesting that you not waste your time and hers by pursuing something you already know isn’t going to work.
And before you say that you don’t know if this will bother you since you just met her, let me just say that her face won’t be changing and it bothers you enough for you to post on a public message board about it. Perhaps you feel that you can spare the time and emotional investment for something like this – I’m just suggesting that she might not, given that she doesn’t know what you’re thinking. If I knew what you were thinking, I’d hope that you didn’t waste my time.
I wear makeup so rarely I usually have to buy new stuff every time I do. I hate the stuff. It’s icky; it makes my face hot and greasy; and makes my eyes feel sleepy. And I can’t touch my face. Seriously, I can’t imagine why any guy would *want *women to wear that crap. Have a female friend make you up one day. Walk around for an hour or two with the stuff on your face. You might understand why some of us choose not to subject ourselves to it then.
I’m comfortable going without makeup in public. It’s not that I’m “not trying to be pretty.” It’s that I think I look pretty enough without a facade. WYSIWYG is a good philosophy to live by.
You’re not wrong for not finding her attractive, any more than another woman would be wrong for not finding you attractive because of your height. And one more date wouldn’t be the end of the world; you’ll both get a better chance to assess your respective personalities. Who knows? She might not like something about you, and this whole question is for naught.
But no, you can’t mention it, as I hope you realize by now.
There are ill side effects that are not health-related, too. You might dislike not being able to touch your face at all. You might hate the way it feels. It might make you break out unless you buy the really expensive stuff, and you may not want to invest in something like that just to please a guy. You might never have learned how to apply it to best effect, so it doesn’t really make you look better, or it makes you feel more awkward than pretty. You might not want to take the time. You might resent being expected to paint over what you were born with because others think it’s not good enough the way it is. These are all valid reasons not to wear make up. A woman might, justifiably, feel that a man who expected her to wear it didn’t think she was pretty enough without it, and that would be hurtful. I think the OP gets the message now.
You might dislike not being able to touch your face at all (convenience).
You might hate the way it feels (health).
It might make you break out (health)
unless you buy the really expensive stuff (money),
you may not want to invest in something like that just to please a guy (choice).
You might never have learned how to apply it to best effect (convenience),
so it doesn’t really make you look better (choice),
or it makes you feel more awkward than pretty (choice).
You might not want to take the time (convenience).
You might resent being expected to paint over what you were born with because others think it’s not good enough the way it is (choice).
As you indicate, there are a variety of issues; my gut reaction to the OP was, “She’s choosing not to wear it.” The woman who doesn’t put on makeup doesn’t have to justify it to me or anybody else, certainly.
Maybe, as others have posted, they only wear it for special occasions, and a date with him might qualify as such for her. But if we knew for a fact that she cannot wear it for health reasons, that would mean that she won’t be wearing any on the second, third, and umpteenth dates either.
I say this b/c I know some women look spectacular when they put it on. Count me among those who don’t expect it but who definitely appreciate it on those special occasions. The OP may be one of our group and “once in awhile” may be enough for him.
I’ve only met a couple who really needed a crash course in its application and I assume if she felt it were important, she’d seek someone who could teach her.
Couldn’t have said it better.
So has she. Commercials, print ads, articles, samples, makeovers at the mall. I don’t think there is a single Western woman alive who wouldn’t know where to go to buy make-up or have it applied, if she wanted. (And waterproof make-up can be a real bitch on some skin types).
Aren’t those the same women normally labeled ‘high maintenance’?
I don’t think I’ve ever heard a guy wish a woman would wear more make-up. I’ve heard men complain about women who spackle it on, and love for the ‘natural’ look (which, let’s be honest, usually involves at least four products and 15 minutes), but never anything like the OP. As others have suggested, you are certainly welcome to your opinion, but I can’t imagine mentioning this to her would result in anything but a punch in the nuts.
This is a really important point, too - from what I’ve seen here (and from my own life), women who choose not to wear make-up are very conscious of the choice they are making and what it means.
Where did this come from? I did not get the impression that the OP was any sort of metrosexual, but maybe you hang with a different kind of guy.
Okay, my point, since it obviously whooshed right by you, is that the OP feels like *his *normal natural face is good enough, without additional enhancement, to attend a singles’ event but wants to know if he can tell a woman he met that *her *normal natural face is not good enough to meet his specific standards. He did not suggest that she choose better clothing or groom her hair differently. She could have been wearing nail polish, he didn’t say.
A person’s face is what they choose to show the world. If it’s okay with her, who is he to even suggest she do something different? Okey-dokey?