He Thinks He Can Make Fun Of Her Appearance And Get A Date???

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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 am 35, live in England and have just purchased your book. I realize now that I’ve being doing the exact opposite of what you preach. No wonder I wasn’t getting anywhere with girls and kept getting dumped after the first few dates. You probably know the sort of mistakes I was making: paying a girl too many compliments, being too needy, never saying no, and being too eager. Now I think that after all these years of unsuccessful dating I’m starting to see the light.

Now here’s my question. When you’re flirting with a woman, do you think it’s okay to joke about her appearance? Not in a nasty way, of course, but in a lighthearted, funny way. In other words, a gentle bit of teasing. For example, if you work with the girl, you might say that you never see her doing any work and that all the inactivity is giving her a fat behind. Or if she has had her hair done, can you say something like “I like it, but next time make sure they do your roots as well?” The point is to throw out some bait about your interest but not come on too strong.

The reason I ask is because there is a girl I work with who I like, and I know that “Caprice” had high Interest Level in me at one time. However, because I didn’t have “The System” I made the same mistakes, like pushing too hard, etc. and her Interest Level has dropped. I am hoping it’s not too late to turn things around, as I really like this girl. Maybe some easy joshing would help?

By the way, Caprice is currently breaking up with the guy she lives with. They have been together a few years and she is having a really hard time of things, as she wants to walk out but doesn’t really have a lot of options on where she can go. We have kissed on a couple of occasions, but no more that that. With her having so much on her mind at the moment I don’t want to put any pressure on her but at the same time I hope I wasn’t just a rebound thing either.

Any advice you can give me would be greatly appreciated.

Anton - who’s trying to figure out what to do next

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Hi Anton,

What you’ve done after getting hold of my book – examining yourself and becoming increasingly self-aware -- is what most men don’t do. Most guys will never sit down and write the names of the last 10 girls they went out with and figure out what went wrong, who dropped whom, whose fault it was, and then take a long, hard look at those ugly numbers. Why? Because the male ego wouldn’t allow them to even think of something like that. “All women are illogical and unpredictable” – that’s the excuse men use to rationalize their failures with the opposite sex.

Anton, all the blunders you made over the years with girls can be boiled down to a single phrase: “too happy to be there.” Remember that, guys. You never want to be too happy just to be there.

Now let me get this straight. You want to WHAT? JOKE ABOUT A WOMAN’S APPEARANCE?

NEVER.

Let me repeat myself so you guys hear it loud and clear – NEVER.

The Reality Factor says you NEVER talk about a woman’s appearance unless it’s in a POSITIVE manner. If you don’t, you’re courting disaster, not romance. You think you’re sensitive? Like my cousin Fast Eddie Love says, “When you make fun of her looks, you’re either stupid or you’re looking to get dumped.”

And remember something else, Anton. What’s funny to you – whether it’s crow’s feet, cellulite, or dark roots – isn’t funny to her. Remember, she’s a female. Like my Uncle Jethro Love says, “She’s got four legs and a tail like a dog, but she’s a cat.”

But okay, you want to tell her she’s getting a flabby fanny because you think it’s cute. You’re on the right track, pal, but why don’t you just say, “Honey, I think your butt is as big as Nebraska!” All women would just love to hear something like that, wouldn’t they?

And that crack about her roots….You know what you’re saying here, dude? It’s like your mom telling you, “Ant, you look great in your new outfit, except that the buttons on your coat look like hell.” Think about it. If your mom said that to you, how would you feel?

You’re not really throwing out bait about your interest when you make those comments. What you’re really doing is putting the girl down.

As far as your fix with Caprice is concerned, it depends on how much damage you’ve already done. And you know what I think about going back to a girl once her Interest Level is swirling in the toilet. But since you work with Caprice, ask her out to coffee. But only ask her once. The last thing you need is a harassment case flying in your direction. Like my cousin Rabbi Love says, “No girl is ever worth losing your income over.”

You tell me now that Caprice is breaking up with her live-in? In that case, you don’t spend any time with this girl. You just smile at her, and make sure she sees you when all the other girls are giggling, touching your arm and bumping into the side of your body when you’re standing at the water cooler or getting your coffee. And that’s all you’re going to do. Caprice has to be completely out of her boyfriend’s hair. Until then, she’s not available.

What do you mean this girl doesn’t have any options? You mean to tell me that Caprice is 25 years old, gainfully employed, and she’s never saved a dime so she can’t come up with the first and last month’s rent? Is that what you’re telling me here? To you Psych majors, this girl’s a real winner.

But you’re smitten with her anyway. And you’re kissing her when she lives with somebody else. Buddy, you shouldn’t even be doing that. But I’ll grant you this – she’s got Interest Level if she’s smooching with you. First, though, she’s got to move out. (And don’t forget, she can’t come up with the security deposit!)

You might very well have been a rebound item for Caprice, my friend. But what you’re going to do is this: let her move out, and if the boyfriend doesn’t call or hang around her anymore, that’s when you invite her for coffee at Starbucks. But not until you know it for a fact.

So here’s my advice: DISAPPEAR until the boyfriend disappears.

Remember, guys: if you want her to like you more, tell her how nice she looks – but only once.