Dating, For the Single Writer

There are two kinds of people in this world:  The unattached and those plotting their escape.

I am of the former (again) and as a single writer dating I have learned a lot, and I don’t mind sharing.

Note – I know some of you are not dating, some never have – some never will. But … most of us are gonna have to learn how to do this and believe you me – it’s a skill. You need to prepare – practice even.

So while your mom might say something bat-shiat crazy like “just be yourself” I am going to give you some genuinely helpful brass-tacks advice.

I am gonna start with the 1st date because as y’all know: You can’t get a 2nd date without a 1st one.  All you smart-asses who say “why not just skip to the 3rd date heh heh heh” … a simple calculation reveals that 0 + 0 = 0, not 3, thus explaining your virgin/chronic masturbator status and smarmy obsession with date #3.

Who can I date?

Anyone who will agree to go out with you – really – the world has 6 Billion + people meaning roughly 3 billion pieces of strange ass out there – and that’s if you are hetero.

And ladies – do not be afraid to ask. Only posers are put-off when a lady asks – and we know what causes their “carpal tunnel”.

If you want to narrow it down – why narrow it down? But if you want to I’ll throw out these rules:

Age: You can date people up to ½ your age + 7 years younger than you are. You can go younger if they are attractive. But not much younger – and for God’s sake stay out of the middle schools.  And although not specifically a “1st date rule” (it’s more of a relationship thing) remember the “campsite rule” when dealing with younger people – leave the place (person) in better shape than what you found it in. Be kind.

Looks: Subjective – but here’s a formula to determine how good looking you are: Rank all of your previous dates on a scale of 1 – 10 – add them up, divide by their total number and subtract 2. That’s how good looking you are. Yes – your pillow probably cries itself to sleep at night and yes, the object of this lesson is for you to learn a little humility.

Clients: Clients/people you do business with should not be dated unless they are attractive. Then by all means go for it. Remember – if it goes bad you do not want a complaint coming in from some bitter person that has a face like a bag of Saskatchewan road gravel. That’s just plain embarrassing. If you are gonna get in trouble make sure the trouble is brag-worthy.

Co-Workers: Coworkers should not be dated unless they are attractive. Then by all means go for it. “Don’t get fired for fug” is the rule of the day.

Ok – Ground Rules established we are off to …

Where to go? What to do?

I am going to assume that she (or he) found your “if you were a booger, I’d totally pick you first” pickup line enough of an enticement to agree to meet. So I am going to say … Lunch. Yes – you heard me – lunch.


Hey – You can’t go wrong with lunch.

Lunch has a set start and a set end – and it’s the end you want in case it’s a bad date. And hey – if it’s a good one it just leaves you wanting more.  Lunch is a daytime thing too – and with lots of other lunchers around it’s good for personal security  – unlike say the popular “coffee date” where you exit Tim’s and curse yourself for parking too far away from the streetlight while clutching your car keys between your fingers in case you need to ward off your “date”.

Personally I think hitting a show and getting dessert is good too but it takes longer and it also ends up in a darkened parking lot.

Activity dates (dog-walking/’rock climbing etc.) – meh. I think that’s a reality TV thing. I am talking about dates for real people with busy lives – so lunch it is.

Alcohol! How much?

None! If you are doing the lunch thing you have to go back to work.

If you are not doing the lunch thing I’d concede a glass of wine (for her) and nothing (him). Alcohol is said to loosen the tongue but it does so by cutting off the brain. Save the body-shots for some other time frat boy – it does nothing for you on the 1st date. Note that if you drink – you get ugly. But if she drinks … you get better looking. Capeche? But only 1 ladies.  3 double screwdriver’s and it’s not heartburn you’re feeling – your boob is in the ashtray. That’s just undignified.

Who Buys?

The gentleman always does. I believe that there is some safety in social convention. So – on a 1st date – the gentleman always buys. This entitles him to say no more than he was a gentleman.

True story – one of my female chums dated a guy who split the tab – he paid for his – she paid for hers. Not even “down the middle”. To this day she disparages him while he busily tries to friend her FB friends – all of whom she has warned. Remember that this may be your last date – with her – but you will be out and about again and it’s small world. She doesn’t hate the guy – you can rationalize splitting the tab – but is this how you want to be remembered? “The Cheapest Guy on my FB LOLZ”. ‘cause that’s what you are headed for in spite of all your arguments to the contrary. Because of the internet no one’s bastardry can remain a secret for long. No use pining for the good ol’ days – times have changed.

Bonus: He didn’t tip or contribute to a tip.

What to watch for?

I always watch how my date treats the serving staff – you can tell a lot about a person by how they treat people they don’t have to be nice to. Remember – soon enough they will feel they don’t have to be nice to you either.  If she whips that poor busboy with a broken off car antenna for spots on the spoons (or if she uses terms like “flatware” or ‘silverware” … actually any term but “cutlery”) you are merely a little familiarity away from being held in the same contempt and beaten with a car antenna.

So watch for it.


Always! With 2 caveats:

1: “Sarcasm” is not humour. Sarcastic people come across as bitter. So don’t be sarcastic.

2: Crude Jokes are not too good of an idea – stupid ones are. The 2 acceptable 1st date jokes you are allowed to tell are:

Q) What is the hardest part about eating vegetables?A) Peeling them out of the wheelchairs!

And …

A pirate walks into a bar with a steering wheel shoved down the front of his pants. The bartender looks over and says “Hey buddy! Doesn’t that bother you” to which the pirate replies …

‘Arrrrrr – it’s drivin’ me nuts!”

Ok – so I got a few jokes – but what to say?

Easy. Stick to stuff you are actually interested in – both of you. As for the other person’s stuff: So what if it’s not interesting? At the 1st date stage everyone should be willing to play along. Avoid stuff you might feel compelled to lie about – for guys this means your bench, salary, what you are really interested in and for girls this means height/weight and what you are really interested in.

Amber Alert: Scrapbooking. I never could fake interest in that. What scrapbooking is to men model trains are to women and ne’er shall the two interests meet.

Moving on …


Make eye contact. Sure – her taters are temptin’ – but make eye contact. She’s not an object. She’s an actual person with interests and feelings and some other stuff like that.


Ditch the list. If you have a written list … title it “How to Die Alone” because if you refer to it – even if just mentally – that’s what will happen. He’s there for a date – not a job interview and the “listers” always ALWAYS interview.

Learn to go with the flow

Hey Man!

Have a list. Boy am I gonna get shiat for this one but because men tend to be a little too happy to be sitting across the table from a real live va-jay-jay with legs it might behoove some of the brothers to kind of have a more formal idea as to what makes for a possible second date. Most men realize way too late – like 6 months after the wedding – that they are stuck with a parasite with a va-jay-jay … which kind of takes the fun out of the rest of your life.

You Go Girl!

Talk! Talk a lot. It takes a lot of the pressure off of him – and men dislike carrying the conversation.

Here’s a tidbit for you: Next time you are out in public pick a couple – any couple – and observe: If he is doing most of the talking it’s a 1st date or very early in “the relationship” – if she is doing it all they have been together for a while.

Anyways – remember – be proactive  ask questions/be interested – sitting there like a lump checking off items against “your list” is not enticing.


He should avoid every using “I’ in a sentence as in “I” did this” or “I” will do that. “I” “I” “I” will wear on her and you come across as self-centered. Use ‘We” when referring to your job, your gym exploits, etc because it makes you sound as if you’re a team player with a few friends and helpers.

She should avoid lists. Women tend to list complaints (against other people – usually their ex-es, their mother’s, and former friends) or demands (“I am looking for this in a man”) but it all sounds like “blah blah blah I’m whiny and demanding”.

So don’t do it.

Deal Breakers

These are things that nothing good could come of. So n the 1st date – Aside from nose-picking … I’d say “secks talk” ruins it for most women (i.e. – don’t tell her she looks like a certain porn star you admire and then just dive on into explaining  why) and for men “relationship” talk (i.e. “how soon would you be willing to get serious”). Because if you ask that question he’ll be movin’ on in a hurry. After all – what’s he got to prove to you? It makes you sound desperate.

True Story: Whenever someone asked me that “how soon” question I told them “whoa whoa whoa … whoa. I think that we should have sex 99 or even 100 times – take a break – and decide from there if we want a relationship or not”.That’s a Sam Malone line (from “Cheers”) and yes – I do say that. I wouldn’t think you should though – I’m just witty enough (and damnably handsome enough) to get away with it – you may not be.

Ending It:

No kissing!

Actually – you can. I think guys should leave this one alone but ladies can initiate one if they want – the “cheek graze” and hug is good enough.

If you had a bad time you may be tempted to say ‘Well fuck you very much for this waste of an hour, let’s never do this gain” but don’t give in to temptation – you should always thank the other person for the date (never for “the time” because that’s lame) and away you go.

The Cardinal Rule

Be cool – it’s A) a date and B) only a date.

Act like you’ve been there before

And that’s that.

Happy dating! If you are going to be eventually financially ruined by someone and have your heart ripped out via your colon and spread on a piece of toast and served to the dog … it’s best to get off to a good start!

Later gators – I’ll be back when someone breaks the seventh seal and those who strayed from the true path burn in the fires of Slor.



3 thoughts on “Dating, For the Single Writer

  1. Pingback: One Year of Half-Wit Lit …. and a Bonus Blog Entry | Half Wit Lit

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