Top Ten Dating Disasters (Or Jeff George's Revenge)

Now that I am married (again)--a week and two days today (thank you)--I thought now might be the good time to post a


Top Ten List of My Dating Disasters


The question I get asked the most--I mean, it happens a lot, enough that I'd remark on it--a lot of people come up to me, and they say, Joe, how is it you keep finding pretty women to marry you?  You're grumpy, you hang out with the musical moron twins, and you freely steal your best material from books, music, and film.  Plus, you're a neurotic weirdo with a long history of creepy behavior, who smells like Good Seasons salad dressing when you sweat.  All true.  So to answer this question, we're going to have to go all the way back to the Civil War...


I'm really good looking and charming (for short spans).  This is why I will always find women willing to take a chance on me.  Or to use a sports' analogy: I'm Jeff George.


For those of you not familiar with that reference, Jeff George was a horrible NFL quarterback who played for, like, 17 teams over his checkered professional career, throwing nearly as many interceptions as TDs, and never posting a winning record (or maybe he did but I am too lazy to look it up on Wikipedia). The guy had a lousy attitude, was a class-A dick, and was disliked by just about every teammate and coach, rarely lasting more than a year with the same team, getting cut or traded or released every off season, only to be picked up by another in time for training camp the next.  Why did teams continue to sign this douche despite his piss-poor track record?  Because he had a rocket for a right arm.  Couldn't hit the broad side of a 'roiled-out offensive tackle half the time, but Jeff George could throw harder and farther than damn near anyone who's played the game.  And someone will always take a chance on someone with that kind of natural ability (so much so that about two years ago, when George was, like, 79, Al Davis actually invited him to camp).


So I'm Jeff Fucking George.  Not in terms of throwing a ball very hard, which I can't do (my two brothers can throw 80 miles an hour.  Me?  I'm lucky if I crack 60.  Oh, but I get to draw pretty pictures), but I've got something that makes me look attractive enough on the outside that some team will pick me up, thinking they can turn me into a winner.  And like ol' Jeff my spotty career has been filled with picks and fumbles.  So without further commentary, here are ten of my worst plays and biggest blunders on the dating field (Goddamn, I love a good sports' analogy).


10.  Karen Vernaccini, 1976


I was five or six, and Karen was my first real crush.  A teenager, she was the prettiest of three sisters who lived by the fish hatchery on Longview Drive in my hometown of Berlin, CT.  I'd go over their house every chance I could, longing for those moments when we could be alone.  One of my earliest memories is of one such moment--lying in the grass, my head on her lap, on a hill in the summer, when I remarked, "Wow, Karen, your thighs are really fat."  And that was the last time Karen and I hung out together.


9.  Mindy, 2008


Mindy was a model, blonde and very pretty.  She was also my age.  Dating girls my age is pretty rare for me (although as you'll see, I did it quite often from 2008 - 2009).  So we're talking like 37, 38.  We only had one date, although as it turns out, it probably could've been more, because I think she really liked me. We'd been set up my my drummer, Scotty, from a short-lived Miami band (which I called Three Junkies and a Christian, but what everyone else called...nothing).  The problem with Mindy was I was outta my league.  Or to quote Rob Gordon, you gotta punch your own weight.  What was I?  I was a middleweight.  Or to go back to our football analogy, if you did a comparison of offense, defense, special teams, coaching, intangibles, etc., all the little footballs would be on her side.  I felt woefully outmatched, and this made me ridiculously self-conscious and insecure, and I never stood a chance.


At one point after missing opportunity after opportunity, mumbling incoherently and staring at her shoes, I turned to Mindy.


I said, "Out of curiosity... What's it like to get everything you want in life?"


To which Mindy paused, smiled slightly, and said, "It doesn't suck."


8.  Amy Kross, 1995


This one hurt for a number of reasons.  For those of you who have followed this blog, and my life, you know all about Amy.  If you were a fan of my first band, Something Like Paisley, for instance, you probably know that I wrote 412 songs about Amy.  I could've gone with any number of dates for the Amy entry, like our first date, in which I picked her up at her Greenwich house and stepped on her very tiny dog, or when she let me sleep in her dorm following a Mexican dinner I'd just eaten, and we woke to a tiny room smelling severely of fart, or when we finally ended up in bed together and she abruptly stopped, saying I was "acting like an animal."  But we'll go with this 1994 lunch, when I returned from San Francisco, pretty high on meth, and coaxed Amy to meet me for lunch, and she showed up with another guy.  (And, yes, I paid for both their meals.)


7.  Sandy, 2009


Back when I'd first met the Boys of Belvedere, head B o' B, Rich P., was enduring a particularly brutal stretch of abstinence, and not by choice.  As he approached the one-year mark, Rich often spoke of how difficult it was not getting laid, how after so much time, one wears the stench of failure on his very person, the stink so bad it scares away all prospective sex partners.  I thought Rich was being a little dramatic, perhaps; furthermore, the concept seemed so foreign to me.  How does someone not get laid if he wants to?  Maybe you have to go down the ladder a bit, but surely a slump can be stopped with a little BP and a weak opposing pitcher (and, yes, that is my third sports analogy in a sex-related post).  But Rich P. was right.

When I got back to SF in 2008, I had not had sex for close to 7 months.  I blamed this on Miami, although looking back, the number of opportunities in Miami--slam dunk opportunities (yup, mutherfuckers, number 4!)--were astounding.  I didn't take them; I don't know why.  And now the stink was on me.  Back in SF, my desperation began to wear like  Amy K's room after the chili con carne incident, and it grew harder and harder for me to get any.  I eventually went out on a date with a girl I met at the gym (always a bad idea). She was 37, and it went something like that Family Guy clip ("This is fun! We're having fun, right?!  You tell the best stories!  Me and my three eggs are having the best time!")

We ended up at her place, and started to make out.  I mean, I did the best I could.  It was awkward as hell. Her whole house smelled like dirty wet cat, and I don't think she liked me much either, really.  In the middle of it, I said I couldn't do this anymore and just got up and left.  One of the most uncomfortable nights of my dating life.


6.  Kara, 2009


Also during this same stretch, I went out with yet another girl my age.  And much like Mindy, Kara was really pretty.  I met her during the '09 Litquake.  I was walking down the street with some friends, and these two girls passed us, one blonde, the other something, and I see the blonde checking me out.  Then we're in the taqueria, and the same two women pass by the window, clearly having followed me, and I see them, and they start giggling, and, really, is there anything better than a giggling girl?  I don't care how old, it's one of life's greatest pleasures.  Now, I'm not much of a player type, but this time I went outside, struck up a conversation, got a number, and we went out on a date. And I wish I could tell you what went wrong. Because for the longest time, we were hitting it off, I had her laughing, I was zipping and zapping, just the right mix of my "charming nervous guy thing."  Then my roommate, Rich Rice, showed up with his girlfriend and it all turned to shit.  She never called me back.  I've retraced this night often.  Rich is awesome, a really cool guy.  All I can figure is that Kara was a offended that I'd arranged to meet up with Rich in case the date was going poorly and I wanted out.  Which I had.  Or it could've been that I told her I write gay cowboy songs.  Who knows?  But she wouldn't even accept my Facebook friend request, so clearly I fucked something up pretty bad.


5.  Katie Ross, 1988


Before Amy, there was Katie.  This one breaks down pretty painfully.  One double date, instigated by a mutual friend, during which she sat as far from me as possible, talked little, and went home early, after which I brought my entire band into the studio to record a song I wrote for her called--God forgive me for admitting this in such a public forum--"Sapphire Eyes."  (Jesus, shoot me.) (And, yes, I passed along the recording, with a dozen roses.  It's a wonder how I ever got laid before 25.)


4.  Jo, 1992


Joe and Jo.  Pretty cute, eh?  I was 22.  She was 29.  Very cool.  Jo was the third girl I slept with (I was a slow starter.  Fuck, I'm a slow finisher.)  To date, she is the only girl I have ever picked up in a bar for a one night stand.  I'm sober these days, but I was very drunk in those.  And being very drunk helps you say and do things you wouldn't otherwise (and generally later regret).  She was sitting at the end of the bar at Jack's Elixir, and I told the bartender that I was buying her a drink and to tell her if she didn't want the drink, she could have the cash equivalent.  Which I stole word for word from this Kids in the Hall skit:

Still, I was pretty proud of myself.  And we had sex that night.  Problem was, I was still really hung up on my ex, so it was begrudging sex, the sort where you get a half on and stuff it in just to say you did it.  It wasn't the least bit enjoyable, and the next morning I felt so lousy, I downed half a bottle of Southern Comfort and headed to the sauna to sweat it out, which I later found out is a good way to kill yourself.  This was the middle of a three-day bender, and a mile or so from the gym, I was stopped by the cops.  But in one of the rare pleasant experiences I've had with the police, this cop took one look at me (or rather got one sniff of me) and knew nothing he could do could make me feel any worse.  He told me to get to wherever I was going and sober up.  It helped that the gym was in the middle of the sticks.


3. Megan Montgomery, 1987


Another rebound lay.  Only this time it was coming after my one and only girlfriend, who had just broken up with me.  Megan (not her real name) had been in love with me all through high school, and I knew she'd go out with me. Problem was, I didn't like her.  At all.  She had a nice rack, but that was pretty much it.  I think we went to a movie.  And I'm pretty sure it was Caddyshack II. Which she laughed like hell all the way through.  When it was over, we went back to her parent's house (this is, after all, when we were 17; no one has their own place at 17), and as we're about to get down, I'll never forget this part, her breath stinks like cigarettes and cheap lipstick, and she says, "I have my little friend."  I have never heard a woman refer to her period like that before or since, but that expression still makes me squeamish.


2.  Lydia, 1988


I've stopped using real names in these posts, for the most part.  Unless I know the person really well or they have told me explicitly they don't mind.  Certainly, I am not using the real names of these exes because that would only engender more feelings of animosity.  So Lydia wasn't really her name, but this was my second real girlfriend and the first woman I ever truly loved (this is the ex I was having a hard time getting over when I picked up Jo in that bar).  I met Lydia through my friend Jimmy, who y'all should know by now, since Jimmy is my writing partner and one righteous mutherfucker.  It's hard to fault Jimmy for much, but I still like to rib him for setting me up with Lydia.  This was one of the most defining relationships in my life, but roller coaster ride and infidelities and ups and downs ended up leaving such a bad taste in my mouth, it's hard to look back on our time together fondly.  But like Tom Cruise says in Cocktail, "Everything ends badly, otherwise it wouldn't really end."


On our second date, I got stinking drunk, ended up getting arrested on Lydia's front lawn, and had to be bailed out of jail (by Jimmy).  Can't fuck a date up much worse than that.   


(When I got home from jail the next day, there was a message waiting for me at home.  Lydia had called to say she'd had a lovely time and would I like to go out again.  Which should've clued me in.  Any club that would have me as a member...)


1. Justine, 2009


I ended my 13-month streak with Justine, though not on this first date (oh, she made me wait, and wait...), during which I stammered and acted mildly retarded, and had it not been for her having a soft spot for the socially awkward, there would've been little chance for a second date.  My courtship of Justine borders on the creepy, from my watching her shower next door, to spying on her sunbathing in her backyard, to my stalking her relationship status on Facebook.  Then again, as Justine likes to point out, "It's only stalking if the guy isn't good looking."  Even so, this was some of my worse dating behavior.  13 months can do strange things to a man... When we finally had our date (after I noticed her Facebook status had gone from "It's Complicated" to "Single"), she was pretty drunk, so I got away with a few things, like when she said she was half Puerto-Rican, and I said, "What are you talking about? You're white!"  But on our second date, she was sober, and the pressure was on.  


I had tickets to see the Hold Steady at the Fillmore, and we were going to get dinner before.  I was crazy about Justine and wanted desperately not to screw this up.  You think I would've made reservations, especially in light of the fact that she was vegan, which meant she could eat about four things on the entire planet.  But I didn't, and we ended up eating awful boiled vegetables in some Japanese place. The night was filled with many lowlights, such as her saying how she always got stuck dating "white boys who think they're Native American," clearly not remembering I'd told her on our first date that I was, in fact, Native American. (And I am proud of my heritage.  Damn you all for stealing my land.  [But thanks for the house]).   But the worst came when she asked me why I'd moved back to San Francisco.


"So why'd you move back to San Francisco?" she asked, spearing a hunk of limp bok choy.


"Because I want to be a private investigator," I said (and it was true.  I was trying to get a PI job through my friend, David).


"Why do you want to be a private investigator?"


"Because I'm good at, y'know, lurking."


To which she responded, quite uneasily in such close quarters, "You do know I'm your next door neighbor, right?"


And it is during such moments that being sober really really sucks.


But I didn't scare her away.  And I owe it all to this cannon of a right arm. 'Cause I sure as shit can't manage a play clock or call an audible or wow her with my coolness under pressure.  


Today we have a son, and last week we were married. We have our lovely house in the hills, and life is a pretty sweet fucking fruit.  Which just goes to show you, maybe Nada Surf was right after all, being attractive really is the most important thing there is...