How should I strike up a conversation with a guy I like and drop some hints that I like him without sounding desperate?

Ask him to go to a flea market with you on a Saturday or Sunday morning.

Do you have a class or an activity in common that you could talk to him about? If not, is there something you know about him that you could ask him about (like a sport he plays, or a club he is in)?

Once you are talking to him, let him know you like talking to him, and would like to more often. And you could get his phone number or email address.

I find just saying hi works great, getting past any shyness you may feel. Sounds funny but when you strike up a simple conversation it can usually lead somewhere else when both people like each other.

I rarely ever suggest that a girl should ask a boy out, but sometimes I change my mind, due to the circumstances and this may be one of those times.

The biggest letdown in a guys life is a rejection, when one asks a girl for a date. I know, I have been there. He may have reasons for not asking you out. Can you think of any?

I suggest you find something you two have in common and play on that, in order to give him a hint that you are interested in him. Some guys just need a little encouragment once in a while. Be sure to find something that will not make you look desperate for a date.

One of my first dates, like this, was to go metal detecting. We were alone in a big field, looking for gold or anything of value. This may not be your bag, its just an example.

Try to not put yourself into much pressure.
Just be yourself, strike up a conversation. Make something up to talk. Tell a silly story or something interesting.
Just be you.

It’s not desperate to ask someone to coffee. It’s desperate to keeping asking when it becomes obvious s/he’s not interested.

It’s very possible. Why not strike up a conversation and perhaps suggest you see a film together? That way when you come out of the cinema, you have the film to talk about if he is very shy. Good luck.

Why not ask him to do something: go out for a cup of coffee or a soda. Tell him: “I like talking to you. Want to go grab a cup of coffee?”

Showing interest isn’t “desperate”. I hate that this wrong “definition” is out there.

Desperate is macking on every guy you see because you HAVE TO HAVE A BOYFRIEND, ANY GUY WILL DO!!11!PLEASE!!!1!! or OMG, I MUST HAVE THIS BOY AND NO OTHER FOR AS LONG AS I LIVE YAAAAUUGH!!11!

This doesn’t seem to be the case.

Ask him if he wants to get a slice of pizza after school one day. Simple enough. In any event, just keep talking to him. Small talk is OK. Getting to know him is OK.