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Dating Advice #118 - Dowdy and Unkempt

May 9, 2009 | by Rosie Einhorn, L.C.S.W. and Sherry Zimmerman, J.D., M.Sc.

She's still wearing the same ill-fitting clothes she wore in high school. Is there any hope?

Dear Rosie & Sherry,

I'm writing about my roommate, who could sure use some of your wisdom. Cindy is a lovely person who would like to find a great guy and get married. However, very few men want to go out with her. Cindy is plain-looking and a few pounds overweight, but if she tried to put herself together she'd make a nice appearance. In fact, I know plenty of women who were not blessed with good looks, but who look pleasant and attractive because they pay attention to their hair, clothes and makeup.

I've tried to set Cindy up, but each time I talk to someone about her, I hear something to the effect of, "Not her! I'm not looking for Miss America, but I wouldn't be interested in going out with someone so dowdy." She doesn't attract men on her own, either. She's bright and interesting to talk to, but she's so plain-looking that men who meet her at work or classes never think of asking her out.

I am sure that if Cindy got a flattering hairstyle, used some makeup and got a flattering wardrobe for a 26-year-old (rather than the same ill-fitting a-line skirt and pullover she wore in high school), potential dates as well as potential matchmakers would pay her a little attention. Then, they'd get to know a sweet, intelligent, interesting woman who will make someone a great wife and mother.

This is my dilemma. My subtle hints to Cindy about her appearance do not have any effect. I think I have to be blunt -- that unless Cindy stops insisting on the natural look and fixes her appearance, she's going to be a very lonely woman. I'm sure this will hurt Cindy's feelings, and I'm not so sure she will even listen to me. What do I do?


Dear Marla,

You cannot imagine how many times we are approached with questions like yours, how to make a dowdy or unkempt or overweight person understand that unless they improve their personal appearance, they will have few dating opportunities. Nobody wants to hurt or alienate someone they care about, but it pains them to see a friend or relative constantly rejected because of something as easily changed as personal appearance.

In all likelihood, Cindy is well aware that she does not present herself attractively. Men and women who maintain poor appearance generally do so for one of these reasons:

1) They don't know how to pull their appearance together. Rather than try and fail miserably, they rely on the same unflattering "look" they have lived with for years. A friend such as this needs more than a mere suggestion to have a makeover. If she is receptive to improving, she needs one or two friends who can provide ongoing encouragement, help her find an attractive personal style that suits her personality and taste, help her shop, and teach her to style her hair and apply make-up.

An overweight person who decides to diet usually needs additional emotional support, in the form of a group such as Weight Watchers or Overeaters Anonymous, to help change her lifestyle and deal with the issues that contributed to these eating patterns.

2) They are very unconcerned with physical appearance and don't understand why looks and wardrobe are important to so many people. Often, such a woman will think, "Why do I need artifices like make-up, fancy hair and a fad-obsessed wardrobe? If a man isn't willing to accept me the way I am, then he's not for me."

It's very difficult to convince someone who thinks along these lines that physical attraction is an essential component of every successful courtship. True, for a large number of men and women, physical attraction may be absent at first and develops as the couple gets to know each other. However, each of them needs some kind of "hook" to initially pique their interest in another person. For most people, that "hook" is a visually pleasing appearance as well as non-physical elements.

We want to emphasize that the essence of a person is their soul, and the purpose of a pleasant external appearance is to open up a window to that soul. As such, clothes and hairstyles should be modest and dignified. They must also be neat and clean, to convey a sense that the soul hidden underneath has those same healthy qualities.

A person who is not attuned to these physical qualities should understand that he/she is in the minority, and that there is a good chance his/her ideal mate needs that visual stimulation in order to spark an interest. By acknowledging that their future spouse may have different sensory needs than their own, some individuals who are not concerned with their own physical appearance may be willing to make a change in the way they look.

3) Some people use dowdy looks or a weight problem as a shield. They rationalize that prospective dates reject them because they are overweight, unkempt or unstylishly put together, and think, "If people could get behind those superficial elements and get to know the real me, they'd really like me." Secretly, these individuals are very insecure and fear that anyone who gets to know them won't really like them. They do nothing to lose weight or improve their appearance, preferring to be rejected because of something external and changeable, rather than take the chance of being rejected because their personalities are not good enough!

You may not know the reasons for Cindy's poor appearance. If you choose to approach her, make your point in a non-confrontational and loving manner. Undoubtedly, what you say will hurt, but if you communicate that you are speaking out of affection and concern, you can minimize the discomfort she will feel.

She may take your suggestions to heart and begin to change. However, if Cindy does not want to listen, or if she continues to insist that she is happy with the status quo, there's nothing more that you can do except keep trying to set her up with that gem of a man who, like Cindy, doesn't care much about appearance.

Rosie & Sherry

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