I know from experience that it can work. When I was 21 I dated a forty-one year old woman who I met through friends. We dated for about six months and during that time became very close. I was moving pretty soon and it is because of that we didn't get closer than we otherwise would, however I have no doubt had I stayed, we would have continued seeing each other and the relationship would have grown. People do look down on older women with younger men. My family didn't like it much, the men for the most part did (go figure) but the women in my family had major problems with it. For it to work I think both people have to be secure enough to know that most people in the beginning are going to have issues, but you have to remember, if you like the person, if you care for each other, it shouldn't matter what other people think. I've always enjoyed dating older women. For me it's easier, less drama, and I find myself noticing I have more in common with them. Age is just a number, and happiness is what matters, regardless of how old one or the other is. I firmly believe you can find love in relationships where age is a factor, you just have to be OK with the fact a lot of other people won't be.