Dear Dr. Date,I am …

Dear Dr. Date,I am a 20-year-old virgin male. I make it seem to all of my friends that I have done the deed because I don’t want them to think I am less of a man or some twisted testosterone thing like that. Anyway, I have just recently started seeing someone and my question is, how do you think she would respond to me telling her? Also, if I don’t tell her, do you think it’s possible I could cover my virgin status with her in bed?
— BT
Definitely tell her. I get many letters from people who complain about the sorry state of their sex life and usually their problems all started with the same decision you’re trying to make right now. Most people choose to fake it and although they survive, they never really learn how to have good sex. If you don’t tell her you’re new at sex, chances are she won’t tell you how much you suck at it. Habits will form and you’ll go through your whole life thinking you’re great at sex, when most likely you aren’t. It makes no sense to act all big and talented, just relax and have fun. Many women get a big kick out of deflowering a young buck like yourself. Take it slow and make the subject of sex open conversation from the very start. Stay positive and don’t let your insecurity about your inexperience manifest itself in unattractive ways. The attitude you should adopt is, “I’m new, but eager to learn. Someday soon I’ll be a fantastic lover.”
The best approach to telling her would be to wait calmly until she brings it up. When she asks about sex, then respond, “I’ve never done it, but I’d like to with you.” Don’t put all the pressure on her to teach you how, as that can be a drag. Unfortunately, the most common sources for you to learn about sex are also the worst. Your friends probably don’t know any better than you, and porn videos are unreal and exploitative. Bookstores have several good instructional texts, but nothing is better than experience, my boy.
Sex is great fun and can be experienced in thousands of ways. There are really only a few rules. Be safe and always wear a condom. (Take the time to read the directions and practice putting a couple on at home.) Go slowly and pay attention to the luxurious sensations you experience. The last thing to remember is that first-time sex is usually lackluster. No mysterious transformation will take place and you won’t feel all that different, but it will get better if you keep trying and positively talk about it.