Single After 30: Minivans vs. Miniskirts

Charlie Valentine

If you took the time out of your day to click that link and read my first blog, chances are that you would have wanted to be just like me. Hi, I'm Charlie Valentine. I used to have it all.

I had the fast track career. The successful independent woman on my arm. Two to three girlfriends on the side at any given time. Friends by the dozen, and the social life to go along. And conceit aside, I'm an attractive, well mannered, educated black man in a city that isn't exactly teeming with them. Yeah, life was pretty fantastic. That was my 20's.

By the time I hit 30, though, my once white hot career was sealed in carbonite, only to be found in museums and Wikipedia archives. My friends had all gotten married, had families, moved on. My meal ticket fiance left me for an even bigger deadbeat, and my formerly plentiful supply of goomahs and side pieces decided a man with no steady lady suddenly has very little appeal. Hmm, maybe that George Bush fella wasn't so bad after all.

So if you're reading this, I can only assume we share something in common. We are single after 30. And have no idea what the Hell we are doing.

Maybe I was out of the game for too long. The former First Lady and I spent the majority of our formative years together. I never had to know how to approach a woman, they came to me. Never had to plan a date that didn't involve that shady little motel in Mystic. I missed the creation of the texting relationship. And if you're single after 30, you're probably from the HIV Generation, like me. When everyone was afraid of casual sex, and entire television lineups were geared towards scaring girls into chastity belts. I mean, it didn't work, based on teen pregnancy stats from the day, but it's a different mentality today.

What do you do when your prime years are fading like an old De La Soul t-shirt, and you've squandered your first shot at love and happiness? Easy. Go to the internet. Five tips for dating in a modern world, 7 ways to impress your date, the 25 and a third things women wish I knew that will BLOW MY MIND. I read it all. Maybe could have learned something if I wasn't so confused. For instance, did you know I would be much more successful with women if I was better at sexting? Besides adding a few inches to the totem pole,  I don't even know what that means. Better lighting? Cast extras? What?! Please, I'm dying to know what I'm supposed to do here! How do I advertise my genitals in a more palatable fashion?! 
It didn't take long for me to realize that these people were not writing for me. Twenty-somethings couldn't care less about the plight of their older and wiser counterparts. Trust me. I've dated dozens of them. They don't care about us, and we, frankly, have no earthly idea where we are or how we got here or why in the name of God these children are setting the rules for us. There's no road map for us, no The World Passed Me By For Dummies, no tried and true path to follow here in 2014. So I say no more. I'm putting my foot down. I'm single after 30, and I'm playing by my own rules.

Yet, so far, the results have been less than encouraging. Which is why I'm writing this. Somebody has to chronicle their failures in the hopes that one day, one of us might could figure it out.

Do you know what's out there for a single man after 30? Divorcees, single moms, twenty-somethings, and a group we will just call Other to avoid insulting my next ex. I will dedicate another blog entirely to these four groups in the future, but for now I want to focus on two: age vs. beauty.

A few weeks ago, I met a young lady and her older friend from the office. Young lady, who we will refer to as Likes Me Too Much (L2M©), is quite lovely and obviously enjoying this time in her life of unbridled youth and attention from men. Her friend, on the other hand, is 6'2" of man hating fury, and overprotective to match. In truth, I was really interested in the friend. I'm post 30, girls in their 20s might be fun, but they are also widely immature, and unreliable. I'm not afraid of an older woman with a little baggage that needs carrying. And besides, if you're between 5'8" and 6'3", you're just the right size to be Charlie's Valentine. Unfortunately, this woman had no interest in me. Not a compliment could get past her defenses, not a flirtatious look, or a 'hey how are ya'. I approached her and she turned her back to me. Stonewall. But hey, consolation prize, L2M is really into older men (they all are for a week or two) so I scored myself a date!

Dating at our age is plain confounding. We have two ends of the spectrum to work with, and neither one is particularly ideal. On one hand, younger girls keep you feeling vibrant and virile, a mile a minute epic adventure of everything you yourself loved in your 20s...at least until you've burnt yourself out on too many 4am binges of booze, sex, and vice. Basically, a recurring midlife crisis. Then she gets bored while you're napping and sneaks out in the night, leaving you to clean up her vomit stains and overturned ashtrays. Oh, and use a goddamn coaster next time! On the other hand, an older woman is more likely to have her life in order, even if she's been through the emotional wringer more than a few times. She generally knows what she wants, and is relying on you to lead her around and show her a magical time and treat her like the 20 something you were out with last night. In short, she's great company and more than eager to have some fun. Buuuuuuuut...she's not around tonight because her oldest has soccer in Holyoke, and she's really stressed out because her dad was just diagnosed with Alzheimer's, and her ex smashed her car windows last night, and her youngest is addicted to Alpo dog food, and and and and. It's our first problem but in reverse. WE are the ones who can't relate, and would have snuck out in the night but she was up waiting for her other alcoholic teenage child to come home. Nothing easy.

So L2M and I really hit it off, and I'm so excited to meet a young woman who I feel a connection with. Stonewall, however, won't let her date this handsome stranger without a chaperone, so we make it a double. I've read that having a good wingman is key in these situations. I have a friend who I think is perfect. Women assume he's gay, and even though I'm told he's not, who better than this nonthreatening nice guy to tear down the Stonewall and give me some alone time with this sweet girl of mine? We will call him Fluffy. My instincts were right, we all had a great time and I was allowed plenty of quality time with L2M. I liked her. She liked me...perhaps even too much.

Things were going really smooth for a bit, and I found myself falling for this beautiful girl. Was it possible? Had I found the exception to the 20-something rule? She's the one, I'm just sure of it! Until the day her loyalty to me was tested, and she passed with flying colors.

Social media is another of these modern dating tools I don't really understand. But my old pal Fluffy sure does. Because he really liked L2M. In fact, even though it was quite apparent what his role in our little soiree entailed, he thought it wise to reach out and ask L2M to be "real friends". I'm sure it's code for something. I'm not hip enough to know what, but I was duly insulted. Of course she told me about it, she Likes Me Too Much. That's a special lady.

What, you thought this had a happy ending? A week later I came home to find her cooking a roast in my oven. I never gave her keys. A week after that, she told me she was pregnant.

I asked her if it belonged to Fluffy.

Today's lesson? If you're single after 30, you're going to need an escape route. 

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