8 Scary Things About Being Older and Single

As I continue my long journey of singleness (opens in new tab), I'm encouraged by the legions of other singles who glorify their independence. Some of us are even wearing a ring to celebrate our singleness (opens in new tab) though hopefully no one mistakes it for a wedding band. We are like a secret society, having clandestine singles-only gatherings (opens in new tab) and even a genre of bars named after us. You've heard of "singles bars" but never:

- Just Married Bars

- Not Quite Sure What We Are Bars

- Friends with Benefits Bars

- I Hate Them, but I'm in Too Deep Bars

It's great to have bars named after my status, but with each passing day of singleness, as I get older, it gets a little scarier. Here's why:

I'm Not as Open Minded

I started to get close-minded right around the time I was suddenly unable to sleep in random places, requiring a bed when traveling or staying with large groups of people. I'm so over the dating scene (opens in new tab), and seasoned, that I'm sure I know a girl's entire story/type before I actually meet her. As I get older, I become more of a creature of habit, and I now habitually go for the same type. I used to hang out with more types, instead of assuming and filtering women out.

Society Hates Me

Last time I made the mistake of bringing a female friend home (and keep in mind this was a female friend that everyone knew I was not dating), my mom hijacked her with her plan to have a crab bake in the backyard for my wedding (opens in new tab). Goodness. I don't even have a girlfriend! (opens in new tab) Many people ask me why I'm still single. It doesn't bother me: I won't mind turning into one of those eccentric harcore New Yorkers like Seinfeld's Kramer. But the longer I stay single, the longer I seem to be bucking the trends of society.

I Get Rusty

Now that I go longer between dates, and give fewer people a chance, my habits and "go-to" moves are rusty. I could go on dates just to stay sharp (opens in new tab), but that's not fair to either of us. There are fine points of dating that change with time that must be monitored closely. For example, I ask girls for advice about whether I should call or text to meet up for a first date (opens in new tab). I get:

"Definitely call — it shows you're serious about it."

Or

"Text, be casual."

If I had an established dating method that remained sharp, I probably wouldn't run into these quandaries.

My Wing Men Are Disappearing

It's always fun, and more comfortable, having a group (or I should say pack) of my buddies to hit the bars with. It gives me more confidence. But my single-guy friends (opens in new tab) are slowly disappearing to girlfriends, married life (opens in new tab)...and babies.

I'm Feeling the Pressure

I've had such bad luck in the past (opens in new tab), and I rarely find anyone I'm attracted to. Fewer opportunities means more pressure when there's a rare chance after I actually meet someone interesting. Pressure throws off my game a bit and makes things uncomfortable.

I Can't Party Like I Used To

These days, I get drunk pretty fast, and my desire for late-night food is getting earlier and earlier in the evening. Then there are the nights I'm too tired to do anything but stay in and read Wikipedia, and check out History Channel documentaries. And, when I do make it out, I'm often with couples who call it a night before I'm ready to.

I'm Getting Uglier While the Girls Remain Hot

By now I think I have a double chin — well, maybe I'm just imagining it. These days I spend time looking in the mirror, monitoring the progress of developing ugly features (opens in new tab), like that double chin. Combine this with the fact that I continue to hit on younger girls (opens in new tab) in that just-out-of-college age range, and you have a total mismatch: a getting-uglier old (but not wealthy) (opens in new tab) guy hitting on a consistently cute population.

My Pop Culture References Are Dated

My buddy and I considered being Crockett and Tubbs from Miami Vice for Halloween. But then we thought: "If we are hitting on younger girls all night, are they even going to know what Miami Vice is?"

Do you feel crippled in the dating world as you get older? Do you have similar issues that I have? What different issues do you encounter as you remain single while getting older?

Follow me on Twitter: twitter.com/richravens (opens in new tab)