My friend Tom (name changed so he doesn’t knife me in a dark alley) is a confirmed bachelor. I don’t mean in the coy, 1950’s he-likes-the-opera-but-we-don’t-talk-about-it kind of way. I mean, he’s never had a relationship that lasted longer than an episode of The Client List.

As is typical of people who don’t have to worry about what hijinks their genitalia gets into, Tom occasionally picks up random women at bars. And since he is single, and since any hookup is comprised of two adults old enough to spell the word “consenting”, this is probably none of my holier-than-thou business.

But then, there’s Lisa.

Lisa is a seemingly nice, 27-year-old girl who Tom has brought home several times. She’s cute, she’s fun, and – here comes the slightly problematic part – one could say she enjoys a festive libation, because she’s routinely, eye-crossingly HAMMERED when Tom encounters her, generally around 7pm.

“Yeah,” Tom says with a disturbing measure of either pride or laissez-faire (I’m not sure which), “I’m a Hot Mess Enabler.”

Upon arriving at Tom’s house, Lisa allows Tom to take photos of her which could most politely be described as Unfit for Facebook. And he gets her to perform acts that would make Heidi Fleiss roll over in her grave. (I know she’s not dead, but this would kill her.)  

He then holds her hair while she hurls (always an attractive quality in a booty call), and he thoughtfully forbids her to drive home, dropping her off in front of her home where she presumably “naps” with her skirt up around her head.

Exactly how starving for attention must someone be to take advantage of a girl who is so clearly FUBAR? If there is one truism in life, it’s that we all crave intimacy and companionship, even people like Tom who claim to love being a “playa”. (He’s white, which makes it worse.) And we all want to feel attractive and desired, but I’m not sure how validating it is to have someone think you’re incredibly hot when they’re seconds away from being out cold.  

Tom’s a great friend to the many people who love him. He just sucks at relationships.  He, of course, blames it on the crappy women. I blame it on the man who picks up the crappy women. As Marianne Williamson once said, “It’s not that you attract the wrong people, it’s that you give them your phone number.”

I think it’s never too late for us to discover our inner benevolence. Maybe the next time Tom picks up someone like Lisa, he’ll play Farmville with her instead of asking her to squeal like a pig. And maybe then, a nice girl can stumble across his path. A girl who doesn’t wake up in her driveway and call the police to report a stolen car.

I had dinner the other night with my friend Jenny and a visiting co-worker of hers, Darren, a 49-year-old gay guy. He was warm, sophisticated and well-traveled, and he brought along his 23-year-old son.

Oh, wait, sorry, that wasn’t his son, that was his boyfriend. You can understand my confusion (as could the concierge at the Andaz Hotel in West Hollywood, who said to Darren, “He looks just like you”). When there are more years between the ages of a couple than one of them has been alive, it’s rather easy for unsuspecting onlookers to mistake the younger one for either spawn or a rental.

As someone who came out in my mid-twenties (which was already five or ten years too late and which involved a lot of unnerving man-on-girl activity and a near-miss wedding), I did not spend a ton of time dating guys for whom being able to order a drink was an exotic novelty.

But I’ve noticed that men who don’t come out until they’re 40 or 50 have a tremendous appetite for youth. They want to date it, they want to dress like it, they want to talk like it. My friend Sallie once said, “Guys who come out late spent so much time being someone they weren’t, that by the time they allow themselves to be who they really are, they have to live out the years they missed.”

Wiser words were never spoken. This late entry into the gay game results in a lot of men in their 40’s wearing super skinny jeans and hoodies emblazoned with One Direction, and using words like “Chillax” and “Hater”. It also results in relationship drama that would make the characters on Gossip Girl cringe. A 40-year-old man who has just come out has the emotional maturity of a 14-year-old girl, without the hormonal insanity to blame it on.

On the plus side, if you’re a 50-year-old man who was once married, your 23-year-old boyfriend can be BFF’s with your children, since they’re often the same age. Darren’s boyfriend spends more time with his kids than Darren does, although the kids sometimes tire of the boyfriend’s enthusiasm for skateboarding and prank calling the Apple genius bar.

Don’t get me wrong, I have nothing against dating younger – you need somebody to wheel you around when you’re old. And unless you have kids that you can guilt into it by showing them pictures of the third world orphanage you plucked them out of, or an estate that makes nurses uncommonly interested in your romantic side, it’s up to the spouse. My partner is 8 years younger than me and will gladly push my wheelchair (off a cliff, I suspect).

I just think that one should marry someone within cultural striking distance of one’s own age. Because, after all, if you can’t share memories like Wonder Woman and Hot Wheels, what on earth do you talk about after you’ve redecorated the house?

I spent most of today bitching about President Obama.

Oh, don’t get me wrong, I mostly love the dude. He’s done a reasonably heroic job fishing America’s lifeless body out of an economic dumpster. And this whole gay marriage stance is pretty nervy in an election cycle. The guy’s got nads.

But every time he visits our fair city, my 90-minute roundtrip commute becomes four hours, as the police  -and whatever secret service agents are not currently busy talking hookers down on price – close every thoroughfare within, it seems, a 30-mile radius of the President’s motorcade. Sure, I’d like to eat Peking duck and artichoke salad with George Clooney, Barbra Streisand and Tobey Maguire, too, but not if it means 5 million people have to spend two extra hours wishing the guy selling oranges on the overpass was selling guns.

So I spent a lot of time bad mouthing the leader of the free world today. And then I read that, along the canyon roads that the he took to Clooney’s house, families gathered to cheer the motorcade.

And children manned a lemonade stand with a sign that said, “Presidents drink free”.

At another corner, a boy held up another hand-drawn sign that said, “Will trade Lakers for Bulls if you stop”.

And finally, two guys and two children stood at the end of their driveway with what may be the best sign of all:

“Our gay family thanks Mr. President.”

Maybe I shouldn’t complain so much. Any event that brings out that kind of togetherness and sense of community without planes being flown into buildings is probably worth those two extra hours in the car.

But next time, I’ll wear an adult diaper. ‘Cause once you pee into a coffee mug, you kinda don’t want to use it again.