Sometimes programmers are also good with languages. If he is one of those, then he might consider taking evening courses in whatever language most appeals and then get to know fellow female students.
Sometimes there are organizations or clubs for folks who like Linux or Unix or writing games or some other aspect of programming. While most members are not female it wouldn’t hurt to get involved with a group like that. After all, many of the male members may have sisters, and there is always the possibility of a female member.
Is there anything he does besides programming? If he doesn’t already have one he may want to take up a hobby such as photography. Again, joining groups of folks interested in photography can lead to meeting women with similar interests.
There are any number of interest groups out there where the subject of the group is a built-in conversation starter. Then, once those involved can see what the others are like, the request to go out for a meal or a drink can be made and accepted more easily.
I strongly believe that he would be able to overcome his lack of self-confidence more easily if he has something to talk about on which he is an expert and which his audience wishes to discuss as well. So instead of “looking for love” he needs to look for people with common interests to his and then see what develops over time.