After reading this post, I can relate 100% to you. Especially in group situations, I feel so completely awkward, like I'm naked in the room. It's so tough to try and be outgoing and make friends. I've always struggled with forming friendships; my parents would always tell me that "friends are second, your family is what matters." Having this influence my entire life, and the fact my parents have no friends, I struggled to get close to friends. I only have a few close friends, and of those, I don't really feel safe or trust a single one of them to fully open myself up in a friendship with them. I have had a few boyfriends, but none of them lasted. I don't think you're missing much, only heartbreak. One of my close friends is 23, and she also has never had a boyfriend, and is still a virgin, so you are not alone at all. There are a ton of people just like you and me.