Tag Archives: Dating Advice

“Jaw With John” – Older Woman Gettin’ Wiggy With It

I’m a 57-year-old lady. I have been a widow 23 years and chose not to date while raising my daughter, who is now 26. I would now like to meet a nice man to spend time with, but I suffer from an affliction many older women deal with — alopecia. My hair is very thin, but with wigs and makeup, I look attractive enough.

I’m afraid I’m being deceptive when I meet a man like that. When is the right time to tell a man what he sees is not what he gets? — EMBARRASSED IN OHIO

Dear Embarrassed,

When is the right time? How about if it gets to the point where he will sensually run his hands through your hair as you maybe “roll in the hay”? That sounds like the right time. And remember, he still gets YOU (so he’s seeing what he’s getting) and if he is truly in to you then he will not mind the wig.

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“Jaw With John” – A Potential One That Got Away Shouldn’t Anchor You Down

“I have been with my boyfriend for two years. Until recently, we were inseparable and I loved his company. I got a job that required me to temporarily relocate and be on my own, so we saw each other only every other week. During that time, I gained a better understanding of who I am and how I want to spend my time.

Since then, I have realized that my boyfriend and I may not be as compatible as I once thought. We discussed it, and he’s willing to do anything to make it work. But some things can’t be changed, such as his interests and small quirks he has. I’m having a hard time because I want to break things off, but then I worry that he could be “the one that got away.” Any advice would be appreciated. — LOOKING FOR THE ONE

Dear Looking,

It looks as though absence did not make your heart grow fonder.

You’ve had the opportunity to take a step back and examine things from a far. And from that distance, you’ve seen that maybe this thing you thought was a well-oiled machine was in fact being held together by duct tape and bubble gum.

You shouldn’t be with someone because they may end up being “the one that got away.” That’s not fair to you or your boyfriend. It would be cheating you and him out of potential happiness somewhere else. It sounds like it’s time to let him go and let him find someone who shares his interests and enjoys his quirks.

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“Jaw With John” – Girlfriend’s Strength Has Got Him Pinned

I’m an average guy, fitness-wise. My girlfriend, always naturally sporty, has been at the gym for a year. Our fitness paths collided when I was enjoying a coffee with her and her training partner at home.

On prompting by her trainer, my girlfriend flexed and her bicep popped up so high my eyes bulged. Her partner then prodded me to flex. I didn’t want to, as I knew my muscle wasn’t as developed. The partner felt both our flexed arms and declared mine softer. She then pushed us to arm wrestle.

I am 3 inches taller than she and I am a man, so I thought I should win. Anyway, after two times on the right and once on the left, I ended up with the back of my hand securely pinned down to the table — to their extreme delight. I feel extremely embarrassed.

This has changed the dynamics in our relationship. She will now teasingly flex when she wants something. And she enjoys challenging me in public. I have now been defeated in arm wrestling in front of her parents and a group of her girlfriends. It’s hard to adjust.

— Outmuscled

Dear Outmuscled,

There’s a part of me that wants to tell you “Get over it and laugh it off” because physical strength isn’t everything. But you seem to believe that you have been stripped of your masculinity because of this situation. That sucks.

I’m comparing apples to oranges here, but if a girl beat me I’d shrug it off and go “Damn! She’s strong!” and yeah, I do know some very strong women – one of them plays semi-professional football so she’s tough. But … that’s me. Back to you.

Your girlfriend is proud of her strength and she likes to flex her muscles, pun intended. But it comes at a cost, and that cost is you. Tell her that you find it embarrassing, demeaning and that you would not be subjecting her to the same treatment if the roles were reversed (at least, I hope you wouldn’t) and go from there. Or you could hit the gym yourself and give her a taste of her own medicine…better to go with the first option.

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“Jaw With John” – What Happens Between The Sheets Should Stay Between The Sheets

I have been with my boyfriend for about eight years.

The other night we went out to dinner with my parents. One of their friends came over to the table to say hello. The conversation came around to this elderly friend’s age. She is 80 years old.

My boyfriend asked her “if she still fools around.”

We were all so embarrassed. He showed no respect to me, my parents or to their friend.

He does not think he said anything wrong. He thinks it is funny. He often talks about our sex life in a social gathering, even though he can see this makes people very uncomfortable. I feel this is a private topic. How do I handle this if it happens again? — Not Amused

Dear Not:

Woof.

Ouch.

Other synonyms for falling flat on ones face.

Your boyfriend seems to lack a filter when it comes to things of a sexual nature. This is a problem.

He’s also painfully unfunny. I recommend you talk with him in private and tell him that the things that you two do between the sheets are between the two of you and no one else. If he continually brings it up in other conversations then you might want to kick him out of the bed and see how he changes … or doesn’t.

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“Jaw With John” – Older Man Runs Into Age Difference

*Author’s Note: I really found the header image too funny not to use.*

I’m a 61-year-old guy. I’m not married and I have no children. I regularly run into this cute girl (who is about 25) at a park where we both work out. We make passing comments to each other. Most of the time she is friendly toward me. I would like to ask her out. Do you think our age difference is too great or would it be OK to ask her out? I am in good shape because I work out most days, so I look about 10 years younger than I am. — Older but Young in Charlotte

Dear Older:

Here’s the thing: you need to build up a rapport with her before you ask her out. Don’t be that creepy old guy who hits on younger women randomly. Talk to her first. Maybe run with her and then you can casually see if she’s interested in you/available/wants to go out with a much much much much older man.

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