I will try to keep it up. You motivate me.

First, don’t think of yourself as a hobo. Second, keep your responses both genuine and proportional. Think of your scenario this way:

A woman is being approached by a bunch of men who stare at her chest and act cowed. Then you come along, you’re well dressed, smiling pleasantly, you look her in the eyes unafraid but relaxed, and say interesting things.

You make her smile.

She rewards you with her first non-automatic response of the night – a tiny confession about eating too many Christmas cookies. It’s hardly life changing intimacy, but it’s genuine, and for a woman to confess to overeating to a man she just met is not without weight.

You reward her genuineness with an appropriate amount of interest. A laugh, a statement of camaraderie.

Lather, rinse, repeat. As she opens up more, you escalate appropriately. You overate over the holidays? Me too, let’s talk for 30 seconds about it. You’re studying law? That’s cool, want to talk for 5 minutes about it, over coffee? You love John Ford westerns? I bet you’d look hot in a pair of cowboy boots – do you want to go downtown, maybe see what’s playing at the Artsy movie theatre? I had a great time, but I’ve got to get up for work tomorrow – want to come in real quick and meet my cat?

At any rate, this is the process as I practice it, out of Juggler’s book.

Girls have said I’m really charming, but I never understood why until now….I suppose giving someone a sincere compliment is the basis of charm. Not taking things so seriously is definitely another thing I notice in Wayne’s dialog. Especially when getting shit tested – he’s doesn’t take her shit test seriously, but he answers honestly. And finally, he makes sure the conversation never gets dull with work/school dumb stuff.

Juggler I’ve always been one of your greatest fans…your style is very classy. I like that because it goes along with the way I want to see myself. I suppose we are similar people.. If only I could get your phone coaching for free!

My impression is that when you tell the woman, “I like that about you,” and “You and I are the same,” you’re on dangerous ground. I’d think the way you say it is everything. If you’re talking to a woman who looks like a model, and is wearing a blouse revealing an ample cleavage, what will she think when you tell her that you like her because of her affection for cookies?

If a panhandler told me he liked me because I ate too many Christmas cookies, and then said, “You and I are the same,” I might reply, “Hey, I’m sorry man, but I don’t have any change on me right now.”

I’d think the only way to make it work would be to say it in a very offhand way, and/or to talk past it, rather like an SOI. You’d have to say it in a way that says, “I like you, but not *that* much, and I’m not interested in your reaction to my liking you.”

Is my thinking on this close to the mark?

You write beautifully. Keep up the good work!