I don't know anyone who "likes" your first definition. Sometimes it can be necessary though, if someone else tells us about this person they know from work or something or our parents have a friend's son they want us to meet. We can't always have enough guys to hang around with and our groups don't get enough guys joining casually so we can get to know them over time by hanging out?

I don't see anything wrong though with meeting a guy in a group situation and later maybe deciding to get closer, just the two of you. But, remember, "practice" makes things easier and going out on dates can make dates easier too so you get use to it and can maybe make more friends, meet more guys that way and, when you are in other, similar, "uncomfortable" situations, you can better deal with them.