Tag Archives: Dating Advice

“Jaw With John” – He Wouldn’t Walk 1000 Miles To Fall Down At Your Door

I am an 18-year-old girl. I have been dating my boyfriend for nearly two years.

My boyfriend means everything to me. Although I have made mistakes we would talk and fix things, and everything would be OK.

Last year we both went to university in different parts of the country, so it was like we were having a long-distance relationship. I was OK with it until I met another guy who gave me everything I have been missing. We were not really dating but I had sex with him many times.

Earlier this week my boyfriend found out and broke up with me. It was only after he was gone that I realized he has always been and always will be my everything. I still love him.

I want him back, but he doesn’t want to hear from me. — M

Dear M:

You “[had] been dating your boyfriend for nearly two years.” He “[meant] everything to” you. You keep addressing things in the present tense when it’s clearly the past. You cheated, he found out, he broke up with you, and now he wants nothing to do with you. I don’t blame him. He clearly has ZERO interest in getting back together with you and you’ve only now realized what he meant to you AFTER you cheated on him and he left you.

You can’t have your cake and eat it too.

You should’ve either chosen to be with him or not when you went off to school. Long-distance relationships rarely, if ever, work out. I had a public speaking professor who was vehemently against long-distance relationships – so much so that he presented his argument in a lecture/public speaking example – and it’s stuck with me since. Here’s the good news: you’re 18. You have learned a valuable lesson in life, love, and dating. Maybe this will teach you how to act in your next relationship. Or maybe it won’t. It’s up to you.

Tagged , , , , , , , , , , , , , , , , , , , , , , , ,

“Jaw With John” – Mind The Gap

I am a 54-year-old woman. I have been seeing a 28-year-old man for the past year.

Although I have confided in a couple close girlfriends and he has confided in his two brothers, he has asked me not to disclose this relationship to anyone else. I have respected his request to be on the down low.

I’ve been divorced for over 14 years and have three kids. I had no luck in the dating arena before I met him.

I have no desire for my kids or anyone else to know about this relationship, but I’m wondering: What do you think of a relationship where the age gap is so wide and the woman is older?

I think about it all the time. If same-sex relationships are no longer frowned upon by everyone, why does there still seem to be a problem accepting a relationship like mine?

I wonder what my future is with him, or if we have a future. Am I cheating myself? All I know is that he is brilliant, beautiful, very affectionate and giving emotionally to me. He is just the best overall person I have ever met.

Should I just relax about this relationship or am I just some stupid old lady?

I’d appreciate your comments and advice. — Middle-aged

Dear Middle-Aged:

Watch the movie I Could Never Be Your Woman. It addresses many of your questions, in a cute and hilarious fashion I might add. People never seemed to bat an eye when older men show up with MUCH younger women. I mean, they have, but it is generally more acceptable tolerated more. Just look at Something’s Gotta Give or The First Wives Club: older man with a younger woman. Coincidentally they both starred Diane Keaton but that’s beside the point. Hell, even Anna Nicole Smith did it and people barely flinched (unless they were in that family).

You’re a grown woman and he’s a grown man capable of making his own decisions and he chose you. The obvious question here, if you do decide to keep this relationship going, is what happens when you are 70 and he’s 44 and you’re maybe thinking if slowing things down but he is still active? What happens then? Then, the age difference will catch up.

You also need to address if you want to continue to be his secret lover. At some point his friends/family will find out and so will yours and putting that off for too long could end up to bite you in the ass. Unless you are into that sort of thing…

Tagged , , , , , , , , , , , , , , , , , , , , ,

“Jaw With John” – All About Steve, Who Sucks

I am a 56-year-old woman stuck in a once-good relationship that has turned stale and neglectful.

My partner “Steve” and I met 14 years ago during a rough time for both of us. (I was in a bad long-term relationship and he had just survived cancer.) We seemed to have so much in common and got along so well. Now he seems aloof and disinterested, sometimes spending nights away from home with no explanation.

I get so depressed about this that I could spend an entire day home in bed just thinking about it. I thought about asking his family for help, but I fear they wouldn’t be supportive.

Steve is a great provider. But I keep wondering: How can I get him to stay? How can I get him to stop walking away? Any advice? — Neglected

Dear Neglected:

As soon as you said Steve I thought of The Waterboy and Bobby Boucher’s mom saying this: “[W]hile I’m sittin’ here all day with nobody to keep me company, except Steve?”

Except you don’t even have Steve to keep you company. Steve is gone and you’re stuck laying in bed saying “Woe is me!” Stop doing that! It’s not healthy! He’s dropping hints that he doesn’t want to be around you. Like, HUGE HINTS. Have you tried asking him upfront what his deal is? Regardless, I don’t think this is going to end well. He seems to be halfway completely out the door, literally. It’s best to confront him and see where this all ends. Maybe there’s a silver lining, maybe not, but you need to talk to him to find out.

Tagged , , , , , , , , , , ,

“Jaw With John” – Call Me, Maybe? Girl, Make It Definitely

I recently broke up with my boyfriend of almost three years. After our breakup, a friend, “Bob,” asked me out.

For the past two weeks, Bob and I have gone out multiple times and talked almost every day. He is very sweet and often compliments me.

We haven’t talked about any potential relationship, but it seems clear that he likes me.

Four days ago Bob and I went to get drinks and the movies, and his sister and her husband came along. I met them for the first time.

We all had a good time and I ended the night by telling Bob to call me when he wanted to see me again, but I haven’t heard from him. Now I am confused. I don’t want to call Bob since I told him to call me, but I’m afraid he will lose interest or think that I am uninterested.

What should I do? I genuinely like him and could see us having a relationship together. Do you think I’m moving too fast? — Single

Dear Single:

If you like him, call or text him. He clearly likes you and the fact that you’re wondering why he hasn’t called you shows you like him too. Maybe he just got busy with work or life in general and has forgotten to call you. It wouldn’t be the first time that’s happened to someone before. Send him a quick message about the other day and how much fun you had and see what happens. But remember: be cool.

Tagged , , , , , , , , , , ,

“Jaw With John” – Boyfriend Has Lived In Cougar Town

“I found out a while ago that my boyfriend had a “friends with benefits” relationship with someone 16 years older.

The first time I heard about it I ignored him for a day. Didn’t acknowledge him, didn’t talk to him and felt disgusted by him.

I know guys have stupid, weird and crazy fantasies about older women. I finally got over it because I realized how much I love him.

This topic came up again the other day while we were having dinner with one of my friends. I told my boyfriend out loud how disgusting it was. That woman was almost old enough to be his mom! He said he liked it because she had “the body of an 18-year-old.”

Somehow I sense a little pride in what he did and I want to puke. We haven’t talked further about this because I know it will just turn into a bigger fight. Why did he do this? Should I just try never to think of it again? — Disgusted

Dear Disgusted:

As long as he was of age then there is nothing wrong with what he did. I am pretty sure most straight guys have had a cougar fantasy at some point in their life. C’mon, Stifler’s Mom? Those type of women exist. Trust me. Your disgust is a personal preference but if the gender roles were reversed, with a Sugar Daddy perhaps?, would you feel the same?

You sound jealous and bit butthurt. He has moved on from that relationship and has now found something, I would assume, special with you. I suggest you should do the same.

Tagged , , , , , , , , , , , , ,