Wow! First of all, good for you to accept such a challenge with all those boys! I myself grew up in a family of 6 kids and was permitted to date at 16. Yes, every family has different standards, but I agree completely with Diane. This is the time to encourage Jake to see dating as an opportunity to make friends with many girls and learn how to interact with the opposite sex in responsible respectful ways. My mom always sat and talked with me about my "dates" and we discussed what were good qualities in the guys I dated and what I should be careful of as well. You might not have that talkative relationship yet, but if you stay involved and interested in who and why he is dating, he will learn to date for the right reasons.
I was raised in a pretty conservative home: taught to wait until marriage, be modest in the way I dress, and respect a curfew (though that one wasn't always easy!). Still, because my mom (my parents were divorced and both remarried) stayed involved in teaching me correct principles, many years later I found my wonderful husband. I know that going out in groups and focusing on developing friendships and personal character when I was younger is what allowed me to find such a great partner eventually. All the best to you!