Tag Archives: Dating Advice

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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31/08/2015
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Advice

“Jaw With John” – Close Friends’ Ex Ain’t Gon’ Give It To Her, Happiness That Is

“My close friend has recently moved to another state to start a new life and “experience better prospects” romantically.

After one week, she’s informed me that she is romantically communicating with her ex again via text. He is married with three children and happens to live in this new city where she has moved. While she knows that I don’t approve of the relationship because it will never lead to a happy and fulfilling life for her, I understand that she has moved to a new city with no other girlfriends to talk to and bounce things off of.

Do I just patiently listen to her romantic tales while I know this is just one more round on the emotional carousel, or should I be honest and tell her these conversations make me feel bad and they’re exhausting? It kills me to see her doing this again. She could do so much better. — Disenchanted Optimist”

Dear Disenchanted:

“Happens to live in this new city where she moved”? Yeah, and my girlfriend is Jennifer Lawrence.

You need to tell her that her ex is just that, her ex. No more pussyfooting around. She needs to hear that and then move on and actually pursue better, and actually available, romantic prospects.

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28/08/2015
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Advice

“Jaw With John” – Don’t Let Him Be The Reason For The Teardrops On Your Guitar

“My office hired a new employee two months ago that I’m very attracted to.

We have become great friends and enjoy the other’s company greatly.

I’ve never been so drawn to someone. I feel like a lovesick kid! I think about him all the time and find reasons to be around him, such as running errands with him or going out to lunch together. The problem is that he has a girlfriend, but I don’t know how serious it is because he’s never shown me a picture of her or mentioned her name.

I’ve tried to tell myself to get over him and move on, but my affections grow stronger every day. He’s everything I’ve been looking for in a romantic partner and we have such a strong connection. I’ve kept my attraction for him hidden because I don’t want to make him feel awkward, but it’s getting harder to do. What should I do? — Heartsick”

Dear Heartsick:

“She hardly ever thought of him. He had worn a place for himself in some corner of her heart, as a sea shell, always boring against the rock, might do. The making of the place had been her pain. But now the shell was safely in the rock. It was lodged, and ground no longer.”
– T.H. White The Once and Future King

Your situation reminds me of a time in my collegiate life when I would go down to the front desk when a certain girl was working there and get trash bags for my room. By month’s end I had a surplus of bags and nothing to fill them with, a date with her included.

Unrequited love is a fool’s errand. A door that can only be walked through one way. But you don’t know where the door is.

It sucks.

I once had a thing for a co-worker and we got along well and she seemed as genuinely interested in me as I was in her. She mentioned, in passing, that she had dated some people but never truly gave the impression that she was seeing anyone. So one day, as the day was drawing to a close I saw her and decided that I would ask her out. I did. It turns out she had a boyfriend, but hey, at least I tried. You owe yourself that much. Ask him if he’d like to see you outside of work. The worst thing he can do is confirm your suspicions.

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22/08/2015
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Advice

“Jaw With John” – You’re A Little Late, I’m Already Torn

“There are two men in my life who have been playing ping-pong with me and my emotions for the past year or so.

I’ve known “David” for most of my life. For many years he said he was interested in me and talked about plans of marriage, children and taking care of me.

He never made a serious move until this past year, but he works odd hours and cancels plans on short notice to travel for work. Sometimes he disappears, leaving me in the dark as to what is going on.

For about a week we were officially “dating.” He labeled me his “girlfriend” on social media and soon after that he disappeared. He recently messaged me and said he wanted to get back together, but I’ve been dating “Jack.”

Jack and I have dated for a year but he shows a lack of interest in our relationship. He will tell me he is on his way home, and by morning he won’t be there and he won’t tell me why.

He’ll also go shopping and buy “special” items for himself and not think twice about our household.

When I brought up a plan for starting a healthier lifestyle, Jack treated it as a joke. I decided to break up with him. Then he started a fight with me and we both ended up saying things we didn’t mean.

My problem is I’m not sure which guy is good for me.

I’m not sure what to do now that my emotions are all over the place. I feel swamped with a big decision I don’t know how to make. — Torn”

Dear Torn:

There’s nothing where he used to lie
My conversation has run dry
That’s what’s going on
Nothing’s fine
I’m torn

Natalie Imbruglia, man. She gets you.

This answer is very very very very simple: None of them are good for you. Tell David and Jack to hit the bricks because you’re going to find yourself a new man!

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19/08/2015
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Advice

“Jaw With John” – Single But Not Alone

“I am a single senior male, divorced for over 40 years. NO I’m not gay. NO I don’t hate women. NO I’m not abusive to anyone or frightening to children and puppies.

I am happy and healthy being single. I have many friends, and I am not lonely. When I meet people and the subject of being single for a long time comes up, the usual response is, “I’m so sorry. Don’t give up, you will meet someone.”

My life has been, and is, very fulfilling. I’d like to respond by saying, “I’m so sorry for you. Maybe someday you will be a whole person with a whole life — rather than half of something.”

That would be rude, but do you have any answers for a response? — Happy Singleton”

Dear Singleton:

Have you ever tried saying “I’m happy being single”? There’s no reason to be rude here. But I’ll admit, it can be a bit demeaning to hear people say “You’ll meet someone”, over and over again.

If that happens, be like Jay-Z and brush that dirt off your shoulder and respond that you are comfortable being single.

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