I'm 35, divorced in the last 10 months, and trying to date again after seven years. I'm new to all this and trying to learn as quickly as I can, but obviously I'm a bit rusty. (And I never was real good at the game of dating the first time around.) Friends tell me I'm good-looking; my focus is working out to stay in shape (I'm damn near where I want to be physically), and I do like to have fun.
My question is this: Do you think we all fit into a certain "league" of people? I see some women I want to ask out and friends tell me, "Oh, she's out of your league." At the end of the day, all I want is to date/have a relationship with someone I find really attractive and who can hold a conversation and have fun. And yes, the women I always seem to want to ask out are the ones my friends say are "out of my league."
My first thought is that your friends aren't exactly of the sweet, nurturing variety, are they? While I've often thought that about certain pining pals, I don't think I've ever come right out and said it. (And I'm kind of a bitch!)
But of course there are divisions amongst daters! To think otherwise is to be willfully naive, teetering precariously on the precipice of stupid. Think about it—how would you feel if a 400-pound hunchback with coarse black hairs shooting out of her chin asked you on a date? OK, but what if she was a really great "conversationalist"? No doubt you would turn a blind eye to her witty repartee, huffily shoot her down, and wonder where in the hell she purchased the nerve to ask you out on a date! Who does she think she is?!?!
The sobering thing is, that limber 19-year-old blonde in your yoga class is probably thinking the exact same thing about you. In her world, you're a boring old fart who looks more like her pervy uncle Jerry than someone she'd be seen with in public. (Unless you're rich. All these rules are null and void if you're a gazillionaire; see also, Donald Trump. Blech.) In case you're wondering, I'm not putting you specifically down—if I tried to bust a move on some barely postteen hottie, I'd face the exact same reaction. Actually, probably worse.
The last time you were single, you were in your 20s. Now you're in your mid-30s, and everything is different. Though I'm sure you're a fine specimen of man meat, I'm also guessing there's less hair on top and more on your back. It happens. Therefore, you probably shouldn't be looking to scam on the same babes you did back in the day. Your friends are merely doing what you should be doing yourself— performing an expectations adjustment.
I could be wrong, but I'm guessing your demographics are out of whack. I imagine these ladies you're thinking about dating are much younger than you and probably far more attractive than you have any right to see naked. (I know you claim that conversation is important to you, too, but I doubt your friends are snarking on your targets because they're worried the women are "too smart" for you.) However, the beautiful thing about you menfolk is that you always think you're better looking than you actually are. Conversely, women tend to be far more self-critical. Which is why you might stand a chance.
There's also the Daddy Damage Factor. Some chiquitas only date older out of some bullshit psychodrama that's too boring to get into here. Suffice it to say, their neurosis is your gain.
Since nine times out of 10, dating is just another exercise in humiliation anyway, you really don't have much to lose by reaching for the stars. What's the worst that could happen? She could say no. Big deal. She may laugh so hard she wets her pants, but then you can turn, point, and laugh at her. You don't want to date some incontinent bitch anyway.
Or maybe the unthinkable will happen and she'll say yes. You won't know until you give it a go.
Batting zero? Write Dategirl at firstname.lastname@example.org or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.