Archives for April 2014

How To Date Older Men

oldermenThis … is … my … wheelhouse.

No, I don’t date older men, wise-ass. I am typically the older man in the relationship. And, don’t give me any grief about it. These are biological urges. I don’t choose to be attracted to young, fit women. You’ll need to blame a creator (if you believe in such a thing), or biology. I’m just following instructions left by my ancestors—when possible, tap young ass, most capable of spreading genes.

I’ve just grossed-out everyone who isn’t attracted to me. Fuck.

Forget it’s me speaking. Forget that I have an agenda. Imagine an older Clooney is your subject, and I’m his agent, offering you advice.

Unless you’re a teenager, an older man probably has less energy than you. Keep this in mind when he reacts to your suggestion about biking and hiking with a (more) wrinkled brow. I’m not saying break out the bocce balls or pinochle cards. Something in between, perhaps. How about yoga?

Girl, I know you love to get your dance on. If the “mature” fellow tries to keep up with you as you bounce around to Tiësto, he’s going to wind up sweaty and sore. You don’t want your friends pointing out his sweat stains. You could avoid this by offering a spare pad for his pits … ew, please don’t.

He realizes you enjoy Instagramming silly pet photos, watching TV with your feet curled under you (owie), and eating fresh fruit and Greek yogurt. You can do these things while he does his crosswords. Refrain from commenting on his reading glasses. In fact, be a good girl and keep a spare set in your Louie. Otherwise, expect a shrug when he’s handed a wine list.

If you don’t currently have a kind, old tiger in your life, and you’re considering bypassing the poodle puppy, you must learn the approach.

Act like a lady, but think like your Grandpop. When a delicious young treat expresses interest in Magoo, this is what goes though his mind, slowly:

  • Holy shit.
  • Where are the cameras?
  • Could this be surprise offspring?
  • Did I date her mother?
  • She thinks I’m someone else—a rich someone else.
  • How’s my supply of blue pills?
  • Dear God, if you would kindly look the other way, and allow me to peel down her panties before I die, I will stop saying “fuck” so often.
  • Where’s my ex when I need her? I’ll get someone to take a picture of me and this angel, then I’ll post it and tag everyone.

You’re probably somewhat intoxicated, and that’s OK. Magoo will do shots with you—just not sugary nonsense, and, for fuck’s sake, not blowjob shots. Be a trooper, order two shots of Irish whiskey and bring him a beer chaser. Do not drop that shot into your beer, young lady. Take a sip, chase with beer, then give him a pat on the hairpiece and kiss on the cheek.

Older dogs typically aren’t quite as overbearing and jealous. We realize you’re a flirtatious little vixen. All good. Just try to keep us from seeing or hearing about it. (That should be simple, with our numbed senses.) Also, please keep your shaggy-headed-surfer-dude ex away, or we’ll make him look sillier by challenging his intellect.

Look, if this is all too complicated, call me. Sure, I’ll walk you through it. Visiting hours are until nine. Buy me a glass of wine, and we’ll chat. I promise I won’t hit on you … much.

How To Date Pretty Men

prettymanHe spends more time in front of the mirror than you? Can’t get him out of the closet? (Eh, hem.) Just had his eyebrows and toenails prettied? This little fellow needs custom attention—the kind you’d give as maid of honor.

Before you react to his neuroses, put yourself in his pumps. When you have a hair disaster, how do you want to be treated? Do you want to hear his lies? “Honey, your hair looks fine. Come on. Let’s go.” Makes you want to hit him with an umbrella, doesn’t it?

So, consider that when he has changed his jeans and shirt three times. If he asks your opinion, you know he is just seeking validation, so give it to him. “I think you should wear what you feel most comfortable in, my love.”

Now, one good thing about being out on a date with this prince is that he’s going to spend a lot of time in the restroom tidying things. This gives you a chance to check your messages, post pictures of your food (we hate you for this), and adjust your boob meat toward the center.

If you’re not already dating this dandy, but you find one you’d offer a title shot, he needs to be approached properly.

Anyone that fussy with his appearance has self-esteem issues. Feed him admiration, and he’ll melt for you. Find the thing that’s had the most adjustments, and focus your compliments toward it. For example, if his hair has enough gel in it to mummify a corpse, you know his mane is precious to him. Admire it (without touching) and say something to the tune of, “Gosh, I wish I had your hair.”

If his jeans have a crisp crease, he’s proud of them. Tell him how great he looks in them (not how great they look on him), and ask if that brand makes women’s jeans. He’ll gush.

This sort of fellow doesn’t want his masculinity challenged. So, if you see him sipping from a triangular glass with a sugary rim, do not approach him carrying a mug of beer. That’s intimidating. Wine would be preferable.

Look, it’s not awful wearing the man pants in the relationship. Sure, you’ll be doling out more emotional support than you’ll be receiving, but at least this fellow is less likely to barge in and take a dump while you’re showering. Plus, if things progress and you procreate, two mommies are better than one.

How To Date Recently Divorced Men

justdivorcedBefore you shy away from this guy, consider that a man who was married has a tendency to be better trained. He just might put down the toilet seat, and put dirty dishes in the dishwasher, instead of on the counter above it.

Before you approach this fellow, you need to do some reconnaissance. The trick is, you can’t ask him, because he’ll lie. A man’s ego is quite a fucking burden, believe me. You can’t ask his ex-wife either, because if she tells you he is wonderful, she’s just setting up someone (yes, you) for future commiseration.

You need to observe him in action, and interact with his male friends to see how he responds.

If his ex-wife ripped his heart out, sprayed it with Sriracha, stomped on it, and then tossed it into the garbage disposal, he’s going to be fragile. Every time your mobile phone lights up, he’s going to assume it’s some thick-cocked hunk calling for a midnight rendezvous.


If he did something awful in his marriage like got his secretary pregnant, and shared her vaginal warts with his wife, you need to know this before accepting that free drink. It isn’t a bad idea to Google his ass. If you don’t find anything, go to his hangout and ask a cute bartender about him. Female bartenders know everything about their male patrons. I’ve received a few stop-staring-at-my-ass stinkeyes.

There’s also the chance that his marriage ended amicably. (Right.) No, really. It can happen. My ex-wife and I are still buddies. Seriously. Fine. Whatever. It can happen. You need to discern if he is being honest when he says, “We just grew apart.” Usually, that means they stopped fucking. Or, the fucking became one-way, without nearly the give-and-take it once had.

(Reminds me of one of my favorite jokes: Why don’t women blink during foreplay? There isn’t time. Uk, uk, uk!)

Anywho, if the guy was married for a decade or so, maybe has a couple two-tree kids, and has recently, reluctantly re-entered the dating pool, he could be quite a catch. What this little fellow needs is ego-stroking and encouragement.

You may borrow from these phrases sure to make his manhood swell:

  • Honey, your arms and shoulders look so defined. You must be working out every day.
  • I can’t believe you look so young for your age. Good genes!
  • My girlies as tell me how lucky I am to have a man like you.
  • I can’t believe your ex let you go. Her loss–my gain.
  • You’re such a gentleman. Can you teach a class on how to treat a woman properly?

He’ll be putty, I mean granite in your hands.

How to Date ____ Men


Odds are somewhere between 99% and 100% of your romantic relationships have ended. You are the common denominator, so logic would say you suck at relationships.

I wouldn’t.

You see, at this point, 100% of my relationships ended. Some served their purpose and ended nicely, while others definitely failed. I’ll not take or assign blame to either party involved. Olive oil and balsamic vinegar are each wonderful, but they don’t mix. The problem is in the mixing.

In this book, I lend my expertise as the datee, not the dater. I’m the man who knows men, and how you can net the one you want (for the time being). True, we men are slightly different, so you need to approach your prey appropriately.

Don’t go hunting birds with hammers, my dear.

Let’s say you’d like to date a married man whom, I assume, you’re not married to. That’s quite an evil desire, according to some. I’m not here to judge. Perhaps you want to bed a man who desperately needs something new, and who will leave you alone thereafter. Fine. Well, you need to approach this fellow a certain way. (It’s in here.)

What inspired me to write this, aside from desperately needed therapy I get from venting? Amazon recommended a book for me, like they do, and usually do pretty well. The book was entitled, How to Date Asian Women.

I shit you not.

I thought, What could possibly be any different about Asian women, and what sort of freak(s) would need a fucking book to lay it out? I’m sure it’s chock full of little ditties like “Best to avoiding binding her feet.”

Then I considered all the different breeds of men there are, including, but certainly not limited to:

  • Short
  • Older
  • Hairy
  • Feminine
  • Overweight
  • Brown
  • Drunken
  • Golfers

I’ve got plenty of these breeds in my life. I witness the dysfunctional approaches of interested parties. I slap my growing forehead and exclaim, “You’re going about him all wrong, darling!”

So, whether you’ve targeted or already adopted a man-puppy, Coach Phil is here to help. Have a seat on my knee, ingest your social lubrication of choice (wine is fine), and pay attention. He’ll be yours in no time, kiddo.