How Long Is Long Enough?

Let's talk about dating. I haven't been on a real date in almost 18 years. And by real date, I mean where the outcome wasn't predetermined. Sure, people go on dates with their spouses, but I'm not talking about (nor interested in) that.

What I'm talking about is a forced meeting with a total stranger where you try your best to make a good impression and not come off as a total gozer or phony. I realize that I am not a classically handsome man. I'm rather average. Not Steve Buscemi ugly, but not the guy that makes the ladies swoon either. My best traits are probably that I'm dependable, responsible and respectful. Great for a Boy Scout or your best friend, but hardly the recipe to charm one's panties off.

I've been single almost three months and I'm starting to be intrigued by the idea of dating, but I can't shake the feeling that it would be 'unfaithful' or 'wrong'. Based on the evidence at hand, my wife certainly doesn't share that opinion, but a promise is a promise, right? It's not the sex that bothers me either. It's the idea of any romantic entanglement that seems like some vague type of betrayal. 

This might be a good time for me to refer back to the title of the blog - LETTING GO? Excuse me while I read my previous post on this very topic.

Thanks, I'm back.

I'm think I'm looking for some outside validation that dating is okay. There should be some authority (Miss Manners, Dear Abby, the Pope) that provides specific, well defined guidance. Sort of like "One should not wear white after Labor Day." Is one week for each year of marriage too short? One month for each year?

I'm not sure I want to be celibate that long.

Like I have a say in the matter? I feel sorry for the first woman who says 'yes'.

I asked Best Friend Brian about this and his advice was pretty straightforward.

"When do you think it's okay for me to start dating?"

 "No."

"What?"

"No."

"But you didn't..."

"No."

I still have no idea.

My friends tell me "You'll know when the time is right." I'm pretty sure this actually means that they don't want to talk about my non-existent sex life and simply want me to go away. Who could blame them? I don't even want to talk about this stuff - it's why I started this stupid blog.

Prior to meeting my wife I was pretty much inept around women. When I see guys I would characterize as 'players' I am somewhat in awe of their ability to say whatever is required to close the deal. I have trouble pretending to be someone I am not. I'm also a really terrible liar. I was at a bar last week with Caprini having a beer - and avoiding going home to my soon to be ex-wife. Caprini is a little older than me and a little better looking and was totally hitting on our bartender (who was 23). Now granted, this girl (and if you're 23, to me you are a 'girl', sorry ladies) works for tips and has to be nice to guys like my friend.  But the thing was, even though he was probably twice her age, I got the vibe that if he really wanted to, he could have 'bought her breakfast'.

I was appalled. Probably because I'm a Boy Scout. But I would prefer women who are closer to my own age, if I get a choice.

When I was younger I was also incapable of picking up on clues from women as to their inclinations. If an opportunity could be missed, I was there. Do any of you remember the classic 1991 Seinfeld episode "The Phone Message"? That was me. Literally, upon seeing the episode one of my friends called me.

Click here to see a clip from the episode!

"Hey, remember that chick Heather who invited you to her apartment for coffee after the Homecoming party?"

"Yeah."

"And you said 'No thanks, coffee keeps me up'?"

"Yeah."

"Jerry Seinfeld just ripped you off."

There was also the time when a cute (really cute, actually) friend from Speaker's Board called to tell me she had just stepped out of the shower and thought there was a prowler in her apartment. I believe her name was Jennifer.

"I'm scared. I think there's someone here."

"Um, why are you calling me? Shouldn't you be calling the police?"

"Well, I'm not sure. Can't you come over and check?"

"I could, but in the ten minutes it'll take for me to get there you could be raped and killed. You should really call the cops."

"Please? I'm only wearing a towel."

"Okay, fine. But if you get killed it's not my fault."

*** That's pretty much the exact conversation. No shit. Brian was there. ***


I doubt my closing skills have improved in the last eighteen years, but perhaps middle aged women are more desperate or easy since they are so much closer to death. I can only hope. If you know any desperate or easy single women, please send them my contact info. I'm free Monday through Thursday, but I'll make time on the weekends.

Just don't tell Best Friend Brian.