[dkarl]

My experience is that intimate partners are easier than friends, because whatever awkwardness or other social issues you have, the other person is going to spot it and not go on a second or third date with you unless they can tolerate it. So if you're on a third date, they've already decided that it's provisionally okay with them. Also, I feel like people are way more tolerant of weirdness one-on-one than in groups, because in groups they have to worry about what other people in the group think.

Once you have a partner, or just someone you're dating, they will expose you to other people in social settings, which will give you more practice under a critical and supportive eye.

But that might just be my experience.