I don’t think that it’s a coincidence that the words “Vain” and “Naïve” share the same letters when both words are attached to dating. Case in point: I was chatting with a girlfriend’s younger, single sister and was taken aback by how vain she was and therefore how naïve that made her. Stella is a nice looking girl, tall, mid-twenties and educated. She is a successful website developer, is close with her family and is really funny. Stella’s had terrible luck dating, even worse luck with Jewish guys and has been on and off of JDate with no success.

I love a challenge so, of course, I asked her what she is looking for as I perused my mental rolodex thinking of tall, Jewish guys. The first – and admittedly most important – trait that she’s looking for is looks. As in really good looking. As in gorgeous Calvin Klein model. As I said, Stella is nice looking, not even near ugly, but she’s no Natalie Portman. And chances are that a Calvin Klein model isn’t Jewish. Is it possible that there’s a Jewish Adonis out there who wants to marry a Jewish princess? Sure. But it’s not realistic for anyone, Stella included. Needless to say, I don’t have any male models in my social rolodex so I guess I won’t be setting up Stella with anyone anytime soon… unless she changes her priorities.

It’s also naïve of Stella to think she can meet a Jewish guy when she’s not currently active on JDate or going to Jewish events. She even said that she’s not attracted to Jewish men… but wants to marry one. Ummm? How is that going to work?

Maybe it’s her age making her think that looks are what’s most important and I should give her a break. I, too, had backwards priorities when I was in my mid-twenties. Once she gets a few years of dating under her belt I bet she’ll shift her thinking naturally, but if I can give her a little nudge now…