How does his shyness manifest? For example, is he okay on the phone but just struggles face to face? Is he interested in internet dating? Is he okay once he gets to know people? And what does he like to do? Does he have any interests?
One option might be to get involved in a local group where there are loads of women. Even if he is not at all theatrical, local am dram type groups are always looking for back-stage crew or people who are good at finding/making props. The backstage people get to know a wide group of people (not only other people in the group, but also the 'performers') quite quickly who tend to have a vast social life that you can dip in and out of as you want. These groups usually have more women than men, so you can get to meet more people who are normally very welcoming of new people - and they will make most of the effort!
Don't know if this will help or if it will be too much for him to make the first enquiries and get involved...?
