Dear Shelly and Ricky,

Hey Shel and Ricky- I have a major problem. I have been going out with my girlfriend for the last six months. She is the most beautiful girl I have ever set eyes on, but she is also the most experienced girl I have ever dated. I am nervous about taking our relationship to the next level, because I do not want her to think I am lacking in performance. How do I get over these presex jitters and just do what a real man would do?

—- Hard but hoping

Dear Hard,

What you have is an uncomfortable situation but nothing you should lose sleep over. This is your girlfriend who you really care about and I am assuming she has reciprocal feelings.
Who cares if she has more experience? Just like at every other progression of foreplay, while in the action you figure out who likes what and how you can please your partner.
Now if you are about to engage in sex, it is the same thing. You are considered skilled if you can play along, not by the number of notches in your belt.
Your best guy friends probably know the little experience you have. Ask them for a few tricks. If you cannot bring this up in conversation read a Maxim or any other advice periodical. In the end if you feel like you are hitting a wall, ask her. I am sure she would not mind a session of show n’ tell.
If you want to look real experienced, I have a piece of advice for you. Bring the contraceptive. Take ownership of the upcoming events and understand the consequences. The use of a contraceptive is crucial. Do realize that not every girl is on the pill.
I hear some of my guy friends say, “If she wants it so bad then she should bring it!” Be a real man and take care of it. I am sure the few dollars will be worth it in the end.
Love Always-
Shelly

Dear Hard,

I have a great idea, in fact, I have solved your problem!!! Do not ever have sex with her! Then you do not have to worry!
Sound good? I did not think so.
Sorry to be the one to break it to you, but you may actually have to have sex with a beautiful girl and just get it over with. I know that it is not the best case scenario, but it’s all I can think of.
Jeez, if everyone had a problem like yours, the world would be a much happier place.
Honestly, let me break this down for you. You have been with an “experienced girl” for six months and the fact that you have not taken the relationship to “the next level” has not seemed to be a deal-breaker yet.
I understand your fear that if/when it happens, she will be dissappointed. Just remember that she has gone this long without “sealing the deal” with you, so she must be in it for something more than just sex. I think the best way to get over your jitters is to make like Mike and “Just Do It.”
What if you are lacking in performance??? So what. You obviously do not want just a physical relationship with her, so if she breaks up with you (worst case scenario right?) then you have found out what kind of person she truly is. Who knows, she might like the fact that she can teach you a few things.
Hey, you might actually be good, then all this worrying was for nothing. The bottom line is, you need to realize this is not the end of the world. You can “what if” this subject to death, but you will just wind up driving yourself nuts. Just be thankful that a beautiful girl is willing to sleep with you, that’s more than a lot of guys can say.
So Hard but Hoping, let nature take its course. I think you should focus on all you have going for you instead of this one possible setback.
And just remember:
“Sex is like pizza, even when it’s bad it’s still pretty good.”

Good Luck
— Ricky