Some people need to know they can laugh and joke together in order to have a connection. In which case it is l’toeles.
Laughing and joking and fun is not the “S’chok V’Kalas Rosh” that we are discussing. Please see earlier in the thread.
So on your point, I’m not suggesting they need to interact with the opposite sex in order to be more comfortable on dates. I’m suggesting that they at least understand HOW to have such interaction when the proper time comes, and realize the following:
1. Your date is not to be treated or talked to the way you treat and talk to your buddies.
2. Your date is of the opposite sex, and therefore, you should understand that you will see things differently. Internalize and respect that.
So you believe the real problem is that boys are not getting appropriate hadracha from either their parents or their Yeshiva.