Next time you have a chat, invite him for something without this being an official date.
Suppose he mentions a movie and you both want to see it, here is what you can do:
Next time you talk about a movie you would both like to see, simply say: "Do you want to see it together?"
This is not an "official date" with all the planning.
It is an invitation to share extra time in a casual way.
It is a perfect way to build up complicity and shift the whole "asking him" out thing without taking too much risk.
How do you do that?
You get ready for this type of opportunities and respond to them when you see them.
If it's not a movie, it will be a drink.
If it's not a drink, it will be a party at some friends.
Any occasion is good.
What matters is that you seize the occasion when it arises.
See the opportunity and go for it!
If you miss an occasion, forgive yourself... You'll grab the next one!
If he can't or doesn’t respond to your invitation let it go straight away and change topic.
That way, you'll avoid any awkward silence.
If he does not go with it the first time, don't worry.
It means nothing.
Give him a week or so.
He might be thinking about it and if you take the initiative again too soon, you might sound pushy.
Taking the initiative and trusting your instinct when the moment is right will give you a huge confidence boost, guaranteed!
If your proposition merges with the flow of the conversation, it will sound like the next natural thing to do.
This strategy works wonders!