I belong to a very conservative family and though am well educated, am very shy and introverted by nature. My family always wanted an arranged marriage for me and never allowed me to date anybody in my life. I however have met several guys through family but nothing has worked still for me. I am 29 now. Things never go beyond one meet as it is too formal usually with families being involved. Just in two cases it was that we met a few more times as the guys were interesting but still things didn't materialize. I am not very outgoing and have a very few close friends . Because of my kind of upbringing I am very under confident when it comes to flirting with guys etc ,this in spite of the fact that I am very attractive,and usually become the center of attraction wherever I go ( which happens real rarely ) of course not to mention that my over protective family environment has a lot to do in this case too.
Now the problem is that I have been liking this guy who lives in my neighborhood, since quite a long time. But don't know how to approach him. We hardly ever happen to bump into each other because of our schedules and stuff. This guy also happens to be somewhat the shy and introvert types but is definitely more outgoing than I am. He was into a very serious relationship which ended up a few months back. Immediately after his breakup he seemed interested in me. Whenever we happened to accidentally meet he took notice of me and tried to chat up, but I felt a bit shy and didn't really know how to take it ahead. Eventually it all stopped before starting. Also his sibling doesn't like me and didn't like to see us chat up. After which he started acting a bit reserved around me. Now I strongly feel for this guy and want to take things ahead. How do I go about? Will / Does he like me ? How do I figure out? Its been sometime now since we have seen each other .

Exactly how long has it been?
You can "bump" into him haha.
If you really like this guy, TRY.
Do. Not. Be. Shy.
Yes it will be hard but let him know your interested. Just start a conversation. See if he wants to go somewhere to catch up, see how he has been.

I think if your interested as you say, you overcome your shyness and talk to him, and see if he takes you up on an invitation to talk over coffee. Just ask and see.

Or you can just wait, and see, if his interest is enough to invite you out. That still requires you to more than just shy, but be friendly, and approachable.

You can set aside the fact that you are shy by spending more time talking to each other.

Put yourself in a position where you will be able to converse and get to know each other better. I'm sure that once you've gotten to know each other better, you will both feel more comfortable with each other and will automatically be more open.

Spend some time going to the coffee shop to talk, talk on the phone, go out to places. However, I would not recommend going to the movies, as both of you are shy already, so you don't need to put yourself in a situation where you can't talk.

If you are too shy to see each other in person too often or you aren't a phone person, maybe you can try IM or emailing for a little while until you warm up to each other?

Thanks I wish for your suggestion. The problem here is different though. We hardly seem to meet because of our schedules and as I said, he acts reserved and very much to the point whenever rarely we happen to see each other which again happens rarely. Now the only way could possibly be online chatting on some social networking site which again feels awkward as he might wonder what happened to her all of a sudden. See as our families know each other it really feels odd. May be he was never really interested and probably only appearing interested during the break up phase out of lonliness, you know that it usually happens, u just want to hit it on with someone inorder to forget the pain etc, but now its been 6 month or more and he is back on his own hanging out with his set of friends. I may appear out of place.