Older Guy Dating A Much Younger Woman? | Doc Love - Dating Advice For Men

Older Guy Dating A Much Younger Woman?

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(Editor's Note, this letter was written before Doc's death in August, 2020 but still relevant as Doc's principles are timeless).

Hey Doc,

I’m in my mid-thirties, newly divorced, and have my own business. I recently purchased “The System” in an attempt to understand what went wrong with my marriage and not repeat the mistakes of the past.

After my divorce, but before I bought your book, I met an 18-year-old girl, Jami, through my business. She was and still is a regular customer. Our first date was to a concert. She invited me at the last minute and I foolishly accepted. The second time was to see a movie, also a last-minute invite. The third time was another concert, planned in advance. All three times one or more of her girlfriends came along. The fourth time was dinner with her parents, and I insisted on treating.

From your book it seems I did everything wrong. I bought Jami expensive presents. I complimented her too much. We also e-mailed and texted every day.

Then she asked me for a job at my company. I told her I had concerns about that because I had feelings for her. She responded that she didn’t have feelings for me, but wanted to be friends. I told her it would be too painful. This was all via e-mail and Facebook Messenger.

After this, we stopped communicating for the most part. Occasionally she e-mails asking what I’m up to, and I’ve always responded. In her most recent message she asked for assistance with one of her college projects. (She wants to be an actress, by the way.)

My gut tells me that Jami is an immature, inflexible taker, and that she’s not the one for me, but I find her very attractive. Doc, what should I do? Should I respond to her need for assistance? What do you think Cary Grant would do in this situation?

I would appreciate it if you could give me some guidance on this matter.

Frederic - who got your book a little too late

Hi Frederic,

You didn’t just purchase “The System.” You invested in your life. You decided to protect your sanity. You gave yourself a guarantee that you’ll never have to lie on a shrink’s couch bawling over a broken relationship.

Pal, the vast majority of guys repeat the mistakes of the past. Know what Judy, Caprice, Lynn, and Amber all say? “This guy’s needy.” But let’s get on to your problem.

So, Jami’s all of 18 years old? Come on, Frederic -- what are you going to do, adopt this girl? But you did the right thing by going along when she asked you out. Take note, because this is what I call an “advanced class.” When a girl comes at you, when she invites you out, you have to GO. I don’t care if you’re the third or fourth dude on her list; if you go along for the ride, you might end up number one or two. And that’s why you go for it.

When Jami invited you to the movies that was the second time she asked you out. Freddie, you’re moving up! Then a concert planned in advance? Wow. You started out as hamburger, next thing you know you’re Chateaubriand!

Now, guy, you know I’m against group dates, but you had to go along with Jami when she asked you out with her friends because she’s just out of diapers and needs chaperones. I know this sounds silly, but these 18- to 22-year-olds have to run you past their girlfriends for approval first.

And by the way, you better only get together with this girl at night because I don’t want her seeing your sagging jowls and all those deep lines and saddlebags under your eyes!

It’s perfect that you insisted on treating for dinner when you stepped out with Jami’s parents. That’s exactly what Cary Grant would have done, too. And, hey -- you’re meeting the folks!

So you’re being too hard on yourself, Frederic. You did lots of things right – up to this point. But now here’s the downside.

You only buy expensive presents for your fiancé or your wife. Big mistake, Frederic. You don’t stick 10 or 15 grand on the credit card for someone you're just dating!

My book tells you to limit your compliments. You had the book, but you didn’t MEMORIZE it, and when you were confronted with this stunning 18-year-old (who belongs on the cover of Elle magazine), it’s understandable that you weakened. But you pulled another boner, Frederic.

E-mailing and texting this honey every single day was a huge blunder. To you Psych majors, Challenge means you’re out in North Dakota because the United States Federal Witness Protection Program put you there -- you can’t be found until your next date!

And to ice the cake, you just couldn’t hold yourself back and had to blabber about all the feelings you have for Jami….Frederic, what in the world are you doing baring your soul to her? Talk about begging! Talk about weak!

Of course Jami doesn’t have feelings for you -- but she loved your Visa card. That’s one out of two. But if I were you I’d be friends with Jami – but you’re going to be kissing her on her doorstep. You told her it was too painful to be friends via e-mail? I’ll bet that raised Interest Level at least 10 points!

You and Jami didn’t stop communicating, buddy – she dropped you like a bad habit. When she contacts you from now on, ignore it – you don’t owe her anything so stop wasting your time.

I have no doubt whatsoever that you find Jami very attractive, my friend. And that makes two of you – you and the U.S. Army. How should you handle it now? Disappear. It’s your only hope. What would Cary Grant do in your position? Mostly the opposite of what you’ve been doing.

Remember, guys: Don’t try to buy her.

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