It's kind of funny, I ride with more female riders now then I did before I got married (my wife is one of the female riders
).
When I was single I would never start a conversation with a female rider while riding. If we ended up at the same rest point at the same time I would ask how their ride is going and the conversation would go from there. Once we get to talking i would ask if they have ever rode (insert trail name here, try to use a trail most riders don't know about
). If not I would offer to have them come along on a group ride the next time I rode that trail. Most of the time they would say yes. The fact that the ride will be with a group eases their mind also. If they have ridden that trail, ask anyways
The thing is, us as men, have to conceal that look of "(insert sexist remark
)" and the likes or you increase your chances of being turned down. Unless they happen to be of the same mind set at the time but better to be caucious so you do not sound like an arse.
I have always thought it funny how men get all nervous when wanting to talk to a women they find attractive. Just go for it but be polite. You will never now what could happen unless you try.