These are things that I used to do a lot when I was younger and shy. They really work because they get to the bottom of things. They're indirect and they're very subtle.
If he does reject you, it doesn't really look like a rejection.
1. A simple thing to do is asking him if he is free. Ask him what he's doing this weekend. After he replies, you say, ‘By the way, I'm going to x at x time. Wanna tag along?’
The reason why it's very simple and it works is because you never really ask him if he wants to go out with you.
You're just asking if he wants to tag along.
If he says, 'Are you asking me out on a date?' You say, 'No, I'm just asking you if you want to tag along with me and my friends. If you don't want to tag along, then you don't have to.'
2. Another thing is you say ‘are you busy this week?’ If a guy is interested in you, he will say, 'No, I'm not busy' or 'Yes, I'm busy but I'm free at this time.'
If he is not interested in you, he will say, 'Yes, I'm very busy.'
If he's not busy, all you have to do is say, ‘Oh, I'm doing this with my friends at this time. You want to tag along?’
It's a very useful line. You're giving the guy a chance to say no to you indirectly.
We discuss this in greater detail in my course.... click here.