Tag Archives: High School Dating

06/09/2015
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Advice

“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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04/05/2015
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Advice

“Jaw With John” – Don’t Believe In Any Of This Fate Crap

“‘Bart’ and I dated in high school. After graduation we went our separate ways. We each married and had children. Eventually we both got divorced and started to date each other again.

A couple of years later we lost contact because we moved to different states. He got married again and it did not work out so he divorced. We did not see each other for two more years.

A couple of months ago we searched for each other and finally met up again. We are both 54 years old.

I am still single but he is seeing a girl on and off. He said she was there for him when he was going through his nasty divorce.

This other girl is separated from her husband (but not divorced). It is now three times that he and I lost contact and were able to find each other again.

Now we are back in each other’s arms. I told him I want someone who is not seeing anyone else. He said he is not going to marry this girl or even live with her, but he can’t just walk away. Now he is seeing both of us.

I want to call it a day and walk away but he said we are destined to be together. I can’t get him off my mind.

Please tell me what to do! — Helpless”

Dear Helpless:

If this were a John Cusack movie I would tell you that this is destiny. But it’s not. This is real life. And in real life there is no destiny, only coincidences.

Didn’t you watch The Matrix?

You’re in control of your own life and not some mystical force. Bart is on his own path as well and you need to let him go. Call it a day. Don’t be the “Other Woman” here and live your life.

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09/04/2015
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Advice

“Jaw With John” – You Need A Potential Breakup Song

“I am a high school sophomore. My boyfriend and I have been going out for about two months now. Lately I’ve been feeling that he and I just aren’t working out as a couple, but I can’t bring myself to break up with him, though I do want to tell him how I feel.

I don’t feel comfortable saying anything to him in person (it doesn’t help that we don’t have much time to talk between classes), and though I’d prefer it, I don’t feel that over e-mail or instant messaging is a good way to break up. I would still like to stay friends but am unsure of what to do to end our relationship. — Confused”

Dear Confused:

Lemme tell you something Confused: Tell him how you feel! As a guy-who-eventually-found-out-that-the-girl-he-had-been-dating-didn’t-really-feel-the-same-way-about-him I can tell you that it’s the worst! You can’t keep stringing him along. Right now you’re giving him false hope and that’s the worst thing for a High School guy. And, wait…what about after school? You don’t have time to do it between classes, and frankly you shouldn’t do it at school at all, that will be embarrassing for him, but what about after school? That seems like the best option.

After school, give him the old “We need to talk” and let him down easy. He’ll probably be pissed but what can you do? I know, find a new guy! Or listen to some music, you can’t go wrong. Just don’t e-mail him or IM him, you’re on point about avoiding those.

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