How do i tell my mom about guys?

I really like my mom, me and her have our differences, but we get along. I've dated people in the past, it was nothing serious, but I feel guilty not telling her. I'm not going to tell her about the past, but how do I tell her in the future? Right now I really really like her friend's son. He's cute and Absolutely PERFECT for me. The catch is I can only see him face to face, with my mom and his mom. Should I tell her I'm interested? Or what? Me and him are SO perfect for each other, like you don't even understand. If my mom knew she would hook up us in an instant, but it's awkward...I can't talk to the guy either, no facebook or cellphone, just face to face. Help please :OOO