Do Long Distant Relationships work?

They do, though it takes extra work. You sound skeptical, so I would keep him as a friend and not pursue unless it gets hotter.

If it's just a friendship. People need to realize they can't know someone online or know if there is chemistry or attraction toward someone over the internet. These things are only discovered in person.

Emotionally connected is possible online. But most people who finally meet their LDR person, in person, meet someone they never expect. It's true.

So if the two of you do not have the resources to visit each other, meet and then continue meeting if there is that connection, it's a huge waste of time.

If you two aren't already together and he has know these girls for a long time its not such a huge deal. If you take the relationship further and he is doing this still then I would be concerned. I would keep the friendship.

Only if you are both adults and you are both at an age and stage in life where you guys can get married

I personally don't believe in LD you will always miss the physical part of the equation the bonding one close to another, I can see my self having a LD friend but not a romantic relationship.