Elk Loin Wrapped in Bacon... and question about dating

Yum.... The Ladies went out to Sweetgrass, an aboriginal restaurant in downtown Ottawa. Tres Tasty!  Wine excellent, service fantastic, the meal insane!  So good.  Only complaint: had no room for dessert!  I forgot that the elk loin was wrapped  in bacon, so I was like "what is this skin around the meat?" and didn't eat it. Right at the end, I remembered it was bacon, so it was like I had extra plate o' bacon. How good is that? 

After that we went to my friend's place to chat. She has a crush on this guy from her running group, but she is so shy! It sounds like he is flirting with her, and although he may not be serious (some people like to flirt) it's still a great opportunity! He's on Facebook, and my friend was debating whether or not to join Facebook, get a few friends (incl this guy) and then try to get to know him better (send him a message). But she is so worried about looking subtle. Just ask the guy out for coffee! What is the worst that can happen?  I don't understand at this age (32) trying to look subtle. This isn't high school, ask him out! If he says no, who cares? He isn't going to think any less of you or joke about it with his friends or something.  But I have been out of the dating game for a good number of years. I met my husband on frosh week of University, haven't dated since. 

But am i missing something?  Is it really that hard to ask someone out? They know each other, but it's not too tight of a friendship where it would be wierd if he turned her down.

So the singles out there: how do you meet people?  She just seems so worried about making the first move, and I don't know what I can do to help!