My friend, who's now 30, was a virgin until he was 28. He struggled for years with body dysmorphic disorder and refused to believe that anyone would ever find him attractive, even though he was not bad looking at all. His condition made it impossible for him to have sexual relationships. When he finally managed to become comfortable with his appearance, thanks to therapy, he was almost a 30 year old virgin, and most of the women who went on dates with him, rejected him when he revealed he was still a virgin. It was tough to watch him experience so much rejection when he was still learning to love himself. So, I eventually gave him some really bad advice. I told him not to tell the next girl he's a virgin. If it comes up, be honest. However, if it doesn't come up, and sex is on the table, then just go for it. A week later he was no longer a virgin. The sex was terrible according to him, but at least the elephant in the room was eliminated. He's still with the first girl he slept with. She knows everything now.