But Yackov, if you yourself aren't completely religious yet, why do you expect a very religious girl to be interested. Most will get nervous if they know you dont keep shabbos totally. I feel I have to point this out. I also think you are narrowing down the list of qualified females to drastically.
She doesn't have to be "very" religious. She can be Modern Orthodox Liberal (A term Frumster uses.) and still be a virgin and be okay for me. I call myself Modern Orthodox Liberal too. The other kind of Modern Orthodox is Machmir. I'm very strict on hugging, kissing, and sex, but I will still listen to female singers and if I see an attractive woman, I will still look at her. I also am not opposed to watching TV or other modern things.
This is a tricky one!
My view is if wearing a kippa, then I would almost certainly not look.. Because I would think it is a chillul hashem..
But if I was wearing a hat, then I wouldn't be quite as strict with where my eyes go.. But I tend to keep them lowered. In normal walking - Head up usually .. Fedor keeps his head up and (respectfully keeps his ) eyes down in the stare down against his opponent! I think the RAMBAN(with a Nun) writes in a letter that one should walk like that.
There was one instance where the woman with the most unbelievable legs anybody has ever seen, she was wearing a short skirt and no tights and was walking down quite a religious jewish road. The friend I was with, started slurring his speech, and said(afterwards) He has -NEVER- seen anything like that before in his life. And BTW, He is not jewish and doesn't live a sheltered life.
The whole street stood still watching, including a guy with a beard. Standing still, staring behind him in amazement with his mouth hanging open - not drooling, but open in suprise/disbelief..
It was an uncontrollable stillness, like a UFO had landed..
It happened once or twice in school, a stunning girl would appear, and because we were all 17, she could stun people into slurry silence. And we'd stare into space even after she had gone, until somebody would wake up and wake up his colleagues, out of the daze.
But for that to happen on a busy public street, to guys in their 20s, 30s 40s. I have never seen anything like that before or since..
I didn't always cover my head in public.
But what about synagogue where they know you are Jewish no matter what head covering you are wearing? I like to look at the girls after services. I just don't talk to them.
Well.. there is a difference between
a)being outdoors and looking silently in a sexual way.. A way that is easy with the anonymity of being a stranger in the street (to girls that might sound perverted, but most guys take advantage of it and look in that situation!)
That is probably quite sinful, and with a kippa on, would be a chillul hashem
b)And looking at them because you have to or want to talk to them. Which would happen in or near a shul!
I wouldn't normally let my mind wonder if I am in or near a shul.
It has happened, but even then, only when I was young, and tired and bored and closing my eyes. I wouldn't look at a girl sexually in or near a shul! They would know, and it's not anonymous. Nobody really stares at girls like that in a shul.. And if you did, it would be a very publc thing.. If you did it while in shul, then the whole ladys' gallery would be aware of it.. And even if outside the main building.. Girls are not alone in a shul, they are with friends.. If Your parents are there, and their friends too, it's even worse. It's just not the place at all.. People talk, but it's far from a place for sexual thoughts to prosper.. I would be afraid of such thoughts there! Especially if talking to a girl and within inches of her! sexual thoughts are not for such public situations. They are for private or if you want to be sinful! then for anonymous situations(like a reflex reaction of staring at a girl in the street when in that open free frame of mind!).