Deal or No Deal

How do you know if something is a deal breaker, or if you're self-sabotaging?

To illustrate my question, I use again the example of Cindy Kim. Cindy Kim, for all of his other fine qualities, is sartorially challenged. His shirts are too big and sometimes holey, and he hasn't gotten the message that light wash, tapered leg jeans and white sneakers needed to be retired no later than the series finale of Seinfeld. I would not describe myself as a fashionista, but I am a devotee of What Not To Wear, and I put thought into my appearance.

A lot of women consider it their mandate to rehabilitate a man's fashion sense when the relationship starts (and indeed, a lot of men consider wardrobe advice to be one of the many perks of having a girlfriend). I believe these women are doing the Lord's work, but I'm not sure I could join their ranks. It's one thing to think about changing the way a man dresses, but I think about how I would feel if I started dating a man and he tried to change something about me. I would bristle, and I would wonder why he wanted to date me if he didn't like me the way I was. But I also don't want to be seen in public with an otherwise good-looking guy who dresses like a slob.

Therein lies my dilemma. Is it really a deal breaker if Cindy Kim can't dress himself (and I am unwilling to dress him)? Or am I using my low opinion of his wardrobe as a way to keep distance between us? Being in a relationship is hard work. Being real and vulnerable with someone is hard work. I've wondered for a long time why I didn't have someone, and I think the real truth of it is that I didn't want to do that work. There were probably times (not that I can think of any right now, but there probably were some) when I could have gotten together with someone, but I kept that person at a distance because I didn't want to do the work of being in a relationship.

When you spend a lot of time with someone, there are going to be moments of disunity. The other person is going to get on your nerves or be inconsiderate of your feelings or take you for granted or something. That kind of thing, while regrettable, is to be expected. But if you know from the beginning that there is something about someone that you don't like, how much weight should you give it in deciding whether or not the person is a worthy relationship partner?