Great news, internet! Thanks to overwhelming interest in my Sassy Advice feature here on this blog, I am writing a full-length, self-help, how-to Sassy Advice BOOK.

If you are interested in great relationships, a happy career, and avoiding death, this is definitely going to be the book for you.

Here’s an excerpt from the still-under-construction First Draft. Look for more updates on the book, as well as continued Sassy Advice posts here on the blog!

This is from the chapter entitled: Sex With Others, aka, Relationships.

The Guy Who Was Dropped On His Head As An Infant Scenario

“I’m 23, 5’7” and a relatively good-looking and successful fashion designer. I don’t date too much, and because of my usually respectful mannerisms I don’t get laid too often and usually end up in that “gay friend” category. 

I’ve kinda got my eye on a cutie who works at a trendy clothing store in my ‘hood. It was initially one of those things where we shared a glance and did the whole “eyeball sex” thing the first time I came into the shop. I frequent this store regularly to help promote and do some PR for a club night my friends are doing, (not to mention check out the, uh, merchandise?) so I have actually spoken to her and got her name and even convinced her to come out to the club a few times (on my guest list of course). 

The thing is, I’m not very comfortable about “macking” on girls in clubs and try to avoid it at all cost. So my question is, how do I go from cheesy promoter guy dropping off flyers and free passes, to getting her to come watch “videos” at my place or even just a phone number for that matter? Giving me a way to find out if she is single would be cool too.”

This guy’s ‘game plan’ is clearly lacking. Step 1: see a girl he likes. Step 2: invite her into a social setting in which he is extremely uncomfortable interacting with her in a romantic way.
Time for Coach Kathryn to whip this ‘rookie’ into shape!
My advice for you is threefold, dude.

1. Stop using double quotations when you actually mean single quotations. Otherwise what you say doesn’t make sense, and you’ll end up having a conversation like this:
You: Hey Mandy. I’m wondering if you want to come to my place to “watch movies”.
Mandy: Who said that?
You: I did. I’m asking if you want to “watch movies”.
Mandy: I know you said the sentence, but who said “watch movies”?
You: Me. I said it. “Watch movies”.
Mandy: So… you are quoting yourself? And the quote you chose is “watch movies”?
You: CURSES! If only I had devoted myself more fully to learning and understanding the Kathryn Hogan Patent Pending Metaphor System of Life Understanding!

2. To find out if a woman is single, you go like this:
You: Hey, Mandy, are you seeing anyone in a romantic way, or are you single?
Or
You: Mandy, you are so good-looking that I can’t imagine you being single. Whoever you are dating is a lucky son-of-a-gun.
The second option has the added benefit of complimenting her greatly and expressing your interest in dating her, while also conceding that it will probably never happen and that you are alright with that.

3. You should not say things like macking or ‘hood. They make you sound incredibly ridiculous.

If you would like to be included in the Sassy Advice book, either as an expert or as an anonymous advice-seeker / question-asker, get in touch!