“Jaw With John” – Robbing The Cradle Is Better Than Robbing The Grave

I’m a 16-year-old guy, and am going to be a junior in high school this year.

I’m attracted to a girl, “Randi,” who is a friend of my younger twin sisters. She is 14 and is going to be a freshman at the same school I go to.

We are very close friends, which causes a lot of tension with my sisters and my parents, who think I’m being inappropriate. Randi and I talk all the time, and she has also expressed some interest in me. I’ve been considering whether to ask her out and make it official.

Is my family right about her being too young? She’s very mature for her age. Should I continue to pursue this, or wait and possibly miss my chance? — Slightly Older Guy

Dear Slightly Older:

You’re not being inappropriate. You’re being a 16-year-old guy who happens to have a thing for a Freshman.

You might want to hold off on saying things like “She’s very mature for her age.” That’s the kind of stuff guys said on To Catch A Predator.

I say go after her. You can hold off for a bit as she settles in to the new school surroundings, ultimately still being present and letting her know you’re around to help. Stay her friend and when you feel that the time is right, ask her out.

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