Valentine's day gets tricky

My two oldest boys are 14 and 11.  My 11 year old is slowly starting to indicate an interest in girls. My 14 year old is far less subtle-he's interested and isn't shy about saying so.

As a dad, this makes me kinda nervous.  I certainly don't want them to repeat the silly mistakes I made when I was their age.  And yet, I'm not entirely comfortable talking with them about it. 

On the Sunday before Valentine's day my hand was kinda forced. My oldest was pacing around and finally asked his mom to buy a box of chocolates which he wanted to give to a girl at school the next day.  Mom wasn't convinced it was a good idea; I wasn't either.  But, we certainly didn't want to discourage him.

I finally sat him down on the couch and tried to talk with him about it.  It was awkward.  He ultimately decided that the box of chocolates wasn't yet a good idea and we talked about other ways in which he could let the girl know that he liked her.

For a moment I felt like I had done my fatherly duty--passing on wisom to my oldest son. I encouraged him to talk to me any time that he needed advice about girls.  He nodded, and then asked me whether I had dated a lot of girls when I was his age. "No," I had to honestly admit, "I didn't."  "Well," my son says after a slight pause, "maybe your advice isn't so good, then."