The term “cougar” brings to mind aging women in Miami-style pantsuits with manservants at their beck and call. I'm thinking Stifler's mom in American Pie . Cher. Blanche Devereaux from The Golden Girls . You get the idea. If I picture Hollywood's version of an older woman who fancies younger men, I then live in fear of waking up at 41 with larger hair, gold chains, and a silk sweat suit, hanging out at dark bars with a wine spritzer in hand ready to pounce on the juniors while “Maneater” plays in the background.
There’s a taboo to the term cougar, much like the played out “hipster” tag. No one actually wants to be called one, myself included. However, I am 36 and dating guys a decade younger.
Let me point out, I have nothing against guys my age, and I don't rule them out. But it’s funny (as they say) that as I get older, the dudes I’m dating stay the same age. I’m drawn to the hallmarks of these 20-somethings – the sound of skateboard wheels coming down the street, the sight of postgrads paying for their coffee with quarters. I don’t need a financially secure, established guy. I need adventure!
So I’m deciding to embrace the fact that I am cougar ish – not only that, I’ll also divulge my secrets on how to play the game.
For the sake of making this thing my own, though, I’m going to create a new term, or one I can deal with that also plays to the new city breed of rad ladies like myself. I’m now gonna call myself a sabertooth – the name refers to a female who’s sly like a tiger, but will also go medieval if you cross her.
I’ll share with you the sabertooth tips that work for me, but I should add that this isn’t about hunting for prey. It’s less about a notch on the belt and more about having fun while getting your flirt on with a younger dude.
Dating in SF is hard. No newsflash there. Being a 36-year-old single woman who is covered in tattoos and weighs a flash over 200 pounds doesn’t make things any easier. I need to own my night out. So I start with a little power mix of Stevie Wonder, Al Green, and Marvin Gaye, who give me that little extra confidence as I get ready. I pull on my best vintage dress and cowboy boots, a beat-up denim jacket (with some patches that give away my inner metalhead), and head out with “Isn't She Lovely” looping in my head.
Now that I’m dolled up, where does a sabertooth find her younger guys? Generally, I prefer not to actively seek out locations, but for the sake of your education and entertainment, I’ve narrowed down my best lairs from the last year or so, places with the right balance of atmosphere and attitude.
My first stop for the night is a gallery because I’m an artist and I’ve long been a fan of the local art scene. There are a couple different shows going on tonight, one of which is at Guerrero Gallery, a laid-back venue that supports great talent and super diverse crowds. This is a good spot to flirt, too, since there are plenty of younger dudes brown bagging it here, and everyone has an opinion about what’s on the walls, right? I've had success in the past striking up conversations here just by asking a guy what he thinks about a work of art.
I’m still thinking about the heavy metal shirt quilt that Guerrero Gallery had a few weeks back as I look over Ben Venom’s new stellar show, and I end up talking to a guy from my neighborhood – a 25-year-old artist and carpenter. As we chat, we bond over a love of power tools and decide to meet at my studio so I can show him the furniture I’ve built (the idea being, of course, that we’ll then need to go for a beer across the street).
See? So far, not so hard. Ask a lot of questions, smile, find some common ground, and go with it. I may not end up with a serious romance here, but I’ve met a cool younger guy who also geeks out on art and carpentry … and who, at the very least, I can talk power tools with.
Next, I grab my friends and head over to 24th Street, an essential part of any sabertooth tour. We start with Pop's Bar – a true dive. I always want to wash my hands like five times before I come out of the bathroom, but the upsides are great. It has heavy metal nights, free bacon on Mondays, great Bloody Marys, cheap beer, a pool table, a photo booth for makeouts, and, oh wait … lots of 20-something guys.
My secret weapon here: a little rock 'n’ roll knowledge. Ladies – guys love talking shop when it comes to musical obsessions. At Pop’s, I’ve found that this is particularly true with metal and obscure rock.
I start talking to a cute guy next to me about Black Sabbath. One sentence becomes two, two become four – flash forward a half hour later and we’ve made plans to see a metal show the following week at the Warfield. Now I realize I am pretty forward, but hey, sometimes that’s what works best. I now have a date with a 26-year-old bartender who moonlights in several bands. Me likey.
Next up, the Phone Booth. This place continues along the dive theme, but offers a little more ambience. Dark red lights, wooden bar, stellar jukebox with a lot of soul (no downloads, thank you). The best part about the Phone Booth is that it's a great late-night spot. This is the last bar you go to. You can get away with dancing and having that one drink too many to fuel your liquid courage. Also, anyone can hang here. I look around and we've got all kinds around us – preppy, rocked out, gay, straight, and my favorite Mission drag queen dancing to Madonna’s “Vogue.” I saddle up for a pool game and order a very tall and stiff Greyhound (two of which are enough!).
Across the bar, I spot a guy rocking out a bit too much to some Johnny Cash. He’s wearing a vintage western shirt and holding a beer koozie. Uh, I may be in love. I’m a little too shy to roll up and just start talking, so I slowly drag my group of friends, which has now grown to about nine, over in his direction. After a few smiles, I decide to take a shot and say hi.
We make small talk about beer koozies, then start going into tangents about country music and traveling to the South. Since I’d already signed on for the pool table, I decide to jump right in and ask this guy if he’ll be my partner. All my friends are conveniently dancing at this point, and a little competition is a great way to get to know this one better.
We end up losing, but that 20-minute game was enough and I think this guy is rad – especially when he offers to buy me a beer. Insert girl giggles here.
I discover he's only 24 and still in grad school, which makes me feel like I have super powers for being able to entice someone 12 years my junior. We’d already gone over our mutual love for music, so now it’s time to saddle up at the jukebox and pick out some tracks together. I learn what his favorite bands are, we laugh at the bad songs we find, and we play a few dance jams (because I will try to get him to dance). We are now roped into hanging out for our little 10-song jukebox run (which should work out to about an hour, so we're set).
By last call, there’s no number exchange or specific plans to hang again, but I don't let that bum me out. We had fun, played pool, danced a little, and I’m pretty sure I’ll bump into him again somewhere. After all, we’re practically old friends now.
At the end of my sabertoothing, I track my score: One blaring hangover from the third Greyhound. (What did I say? Stop at two drinks at the Phone Booth!) Two dates planned, one mark left on a future possibility … wait. Actually, it’s not that calculated.
In all seriousness, dating younger isn't about being icky while cruising for dudes. It's about being a bit spunky and letting go of insecurities while in the process, meeting some fun guys.
So I had a second hang with my carpenter buddy and I think it may lead to more than friends. My metal date? We had fun, got some headbanging on, and he still texts me about good shows coming up. Now if I could just see my koozie-slinging dreamboat … but I guess even sabertooths can’t win ‘em all.
Sabertoothing isn't hard. It just takes a little courage, a lot of smiling, and the ability to let go of your inhibitions, especially if you hit my favorite haunts – Guerrero Gallery, Pop’s, and the Phone Booth.