Asking someone out is a risk. You fear rejection. Being asked out is the ultimate in flattery. The issue here is a task focussed issue on just one thing - 'He has to ask me out'
Why would he ask you out?
If you are frozen in fear of even having conversations, build your confidence and start your conversations gradually with complete strangers - the bus driver, the check out operator, the bar staff, anyone in the bus queue. If you relax and think about what someone has just said, then you can acknowledge and agree with them. Be open and be friendly. Most people start conversations with the usual non confrontational 'Oh this weather is awful isn't it?' Socially it allows you both to be on the same page to explore further comments if you both agree initially on something bland and agreeable.
This isn't just about you versus him. This is about you being left behind when everyone else has a 'mate' and it exposes your feelings to perhaps 'never getting a man'?
Fix your own comfort level first with friendly chatting with others and then practice building your confidence so you can just talk away with him. Ignore expecting him to ask you out. If someone asked you, and you decided to say 'no' it could be mildly embarrassing, but they survive. The same applies if you ask him. But think of the positives involved. Deal with this as him being a friend and nothing more. Just because this man is now 'on his own' does not mean he is a good match for you? Get to know him. But if you have the hots for him just ask if he would like to go on a date. What's the worst that can happen? He says 'no' - even if it is a 'no' he knows that he has one more cheer leader on his side than he did previously. And you also live to see another day, older, wiser etc