BMBochur777,
I can really appreciate this question, as I went through an almost identical situation when I was dating. I was dating a girl who I found incredible in many ways, but I noticed over time that her skirts were sometimes a tad short (not very short skirts, but often I would see her knees briefly while she was sitting, etc.) I am a serious Yeshiva guy with very strong hashkofos, and to be honest, it really bothered me. I kept pushing off the issue in my head as I got to know her better. I’m NOT recommending that you do this, but at a certain point when we getting pretty serious (date #10), during a serious conversation, I mentioned to her that there was something I needed to talk to her about that was bothering me. I want to keep this post short, so I won’t go into great detail, but I said it in an EXTREMELY sensitive way. She starting crying and told me that this was an issue that she has been struggling with for a while, but it doesn’t represent who she is. I accepted that answer, but still was unsure what it meant for me. I called my Rebbe who I am very close with and told him the whole story. His response was, “are you crazy? This girl is a diamond! For her to admit to it being a struggle, and start crying about it shows how special she really is. So she struggles with it – we ALL have struggles! Everything else about her is great, right?” And it was…
P.S. We are very happily married for a few years now. She’s a fantastic girl and I respect her tremendously. The same issue does still come up once in a while, and it still bothers me. But we work it through like any healthy married couple work through their “stuff”.
I’m not giving you advice, as I don’t know you or your situation. (I am a Marriage and Family Therapist, and I know too many situations where people got messed up from getting terrible advice that was not well suited for them…) However, I just wanted to share that perspective. Take from it what you’d like.
Hatzlacha!