The Pretty Boy, The Drunk Cowboy, The A-hole, and The Other Cowboy.

I dated a total douche bag in high school. Not only did I date him in high school, but I dated him all through high school. And when I say douche bag, I mean he was a complete douche bag. The douchiest of all douche bags, if you will. The few people that both read my blog and went to high school with me are all nodding their heads while they are reading this chapter because, dude. Douche. Bag.

So I never really dated. And now, as I approach my later 30’s as a married woman, I feel like I dodged a bullet. A big, fat, sexually transmitted bullet. That isn’t to say that I haven’t had a few dates in my life, just, I tend to be monogamous, and most people really annoy me, so I just never got into the whole go-out-with-a-different-guy-every­-night thing. Plus, I’m excellent friend material. So although I have always been adorable, and, really, quite fantastic, I rarely got asked out on a date.

Except for a few times, when . . . well, let’s just plunge right in.

The Pretty Boy

I moved to Virginia after graduating high school, not to go to college but, as it turns out, mostly to go to bars, drink underage, dance to Salt N Pepa, and work a forty-hour work week at a crappy company. My older sister was dating a guy that was a bouncer at various local clubs in town.  He was also in FAST Company, a branch of the Marine Corps where they train you to survive in the woods with one leaf and a sock AND how to kill someone with your pinky, so he was a big, scary mass of a man. For some odd reason, my sister had decided to like me enough to let me tag along with her when she went to the bars her boyfriend was bouncing at. By the time I met Pretty Boy, I had become a bit of a regular at this one particular bar, where I enjoyed a fine beverage called “The Leg Spreader.” Compared to my sister, I dressed conservatively.  Actually, compared to my sister circa 1992, I can confidently say that even Katy Perry dresses conservatively. I’ve seen her throw a suit jacket on loosely over a fancy bra and head out for the night. Not anymore, mind you, but still: the outfits I’ve seen! She drew a lot of attention—never welcomed, but she always handled it sweetly, while I just sat there. Occasionally, when someone really drunk approached us and tried to hit on my sister, I would get to take out my aggression over being ignored and tell the guy to piss off. But usually, I just sat there quietly, pretending to enjoy being invisible. So the night that The Pretty Boy came over to our table, I just sat there waiting for him to hit on my sister until I realized he was talking to me.

I’m sure we had an interesting talk. I was pretty cocky at that age, and if the conversation hadn’t interested me, I would have made it pretty clear. But he was so . . . so . . . pretty! I think his name was actually Dezi or something toolish like that, but he was alright—apart from the toolish name. And the nipple piercings he showed me while we were sitting there. I gave him my number and left for the night, thinking that he would toss it and that would be that. When he called me before the weekend I was shocked but game. I met him again at the same bar where my sister was taking part in a—wait for it—BIKINI CONTEST. Seriously. Even more serious is the fact that she WON the bikini contest and the cash prize that came with it.

Later in the evening, something happened that has only happened to me once in my life and will never, ever happen again. Ever. Ever, ever. I was dancing with Pretty Boy, and a man was dancing to my left but continually trying to “move in” on us. Over and over again this guy tried to move pretty boy out so he could dance with me. Pretty Boy confronted him and, all of a sudden: a brawl. I swear to the sweet, invisible, possibly-nonexistent Lord that I am not exaggerating when I say that a brawl broke out. Over me. And my sweet dancing skills. And my big hair. It broke out so bad that I was knocked down and kicked in the head five times, my sister was pushed over and all her bikini prize money stolen, and the entire bar had to be cleared.

That was the last night I saw pretty boy. He was pretty upset that his gold chain had broken in the fight and his Italian Horn pendant was lost. Never mind my mild concussion.

The Drunk Cowboy

Another bar, another night. I was in a terrible mood when I encountered the Drunk Cowboy. I had just watched my sister be approached six different times by six different guys (all of whom were turned down) and had endured the worst pick-up line of my life (a 60 year old man asked me for a quarter so he could call my mom and thank her for giving birth to such a beautiful girl). For reals.

So when Drunk Cowboy came over and asked me to dance, I said no thanks. He seemed surprised, but it was hard to tell with his giant hat. He walked away and came back 10 minutes later, leaving again when I said no thanks. When he came over the third time, I just felt bad for the guy. One dance couldn’t hurt, right? And it was a Color Me Badd song, so who wouldn’t want to dance to that? On the way to the dance floor, he stumbled a little, but recovered, so I paid it no mind. Here’s an exact transcription of what followed:

“Hi! What’s your name?”

“Sarah, what’s yours?”

“Drunk Cowboy. Where you from?”

[He begins to sway, and it becomes obvious that he is wasted. Like, waaaaaasted.]


“So, what’s your name?”

“I just told you. My name is Sarah”

“Where you from, Sarah?”

“I just told you that too, Syracuse.”

“Oh. Well, what’s your name?”

O.K. Multiply this conversation by four, because I’m getting tired.

By now I know he’s wasted. It’s as if all the alcohol he has ever consumed throughout his entire life caught up with him at the exact moment. And after he asked me where I was from, for the fourth time, I watched as his eyes rolled back in his head, and he fell flat. Not knees-to-chest, but flat on his face in the middle of the dance floor. And he was out. And so was I.

The A-hole

It’s probably my fault for having pursued the A-hole. We actually met over the phone while I was at work. At times I can be funny, and when I’m on, I’m on. This day, I was on with a capital O. A-hole called; I cracked him up, and he called again. And again. Eventually I gave him my home number, and we began a long-distance relationship. We were close in age, but not geography—I lived in Virginia, he lived in Chicago. We spoke daily for months. We exchanged mix tapes and photos through the mail, and eventually I asked for a plane ticket for my birthday in order to fly the A-hole to our house for a visit. We clicked in person and got even closer—so close that after he left the first time, it was only a couple of months before he flew back out for another visit. This visit wasn’t as dreamy, and when he left, I was feeling sort of done with the whole thing, but we spoke about some things and committed to continuing our relationship. So we did. Until one night . . . my phone rang.

Here is the conversation that occurred:

“Hi, this is Sarah.”

“Hi, Sarah, this is Susie, and I want to know what you are doing calling and mailing my fiancé?”

“I’m sorry, what?”

“I’ve been engaged to A-hole for 2 years now. Who the hell are you?”

“I’m the girl he’s been dating for 6 months.”

“Well, I thought you should know that he is engaged to ME, and you should stay away from him.”


It ended pretty well with her, actually. She was pretty understanding, considering I had no idea that she existed until that phone call. I broke it off with him right away, and in a very, very, very loud manner. So loud, in fact, that he replied, “Wow. I had no idea you were such a bitch!” Years later I saw him and he was all greasy and bloated. Single too. So I felt better.

The Other Cowboy

Yes, there is more than one cowboy in my life, sort of like there is more than one pendulum in my life. This one was sober, though, and you will soon see why.

When I lived in Virginia, I lived with my Mom. She had a housekeeper who came every week, and one day it was discovered that she had a son. He was my age and—lo and behold—single! What luck! So, a date was made. A blind date.

I’m pretty confident that people only have one blind date in their lives. When I opened the door to my blind date, I opened the door to an evening suckfest. There was the hat, there was the buckle that said something like “Kentucky,” and, let’s not forget, the tinted glasses. He had a stringy mustache and pale skin, and, at age 18, he was already sort of doughy looking. Then there was “the arm,” which, in and of itself, was not an issue. He had a “dead” arm, that hung at his side, and because I had no previous knowledge of it, I lingered on it as I sort of looked him over. He picked it up with his good hand and let it drop while he said, “I fucked my arm up.” And off we went.

He took me to Pizza Hut. Pizza Hut, people! Not even Applebee’s or Chi Chi’s! And it was the single most awkward evening of my life—not because we didn’t have some sort of conversation, but because of his arm! This guy was freaking traumatized over his arm! When the pizza came, he insisted on cutting it a second time, and he did it in such an angry, one-handed way that the pizza almost fell off the table five times. He talked about his drunk driving accident the entire time, and let me just say the story wasn’t that long. I mean, he drank, got drunk, drove, and hit a tree. He got a ticket, a DUI, and a dead arm out of it. End. Of. Story. I began the evening compassionate. I ended the evening wanting to kill his other arm. After Pizza Hut, and hearing the same story for the third time, we went for a drive. Where did we go? Let’s see . . . where would a completely traumatized cowboy go? Back to the scene of the crash, of course! Not once, people, not twice, but a total of three drive-bys. “Here is where I must have passed out. Here is where I skidded. Here is the tree . . .” And the entire time we were on this drive, I had to listen to the same REO Speedwagon album over and over and over again. I wanted to take the wheel and smash us into the tree.

All of this happened in Virginia. Turns out Virginia really is for lovers! I moved there in 1991 and left in 1993 and in that time had more bad date experiences that I’ve ever had in my entire life. I’m leaving some out here, to spare you the stories of The Impotent Soldier and The Cheating, Bomb-Planting Kickboxer. Already I’m on page four, and I don’t want to lose you all forever. So what I want to do now, if you have stuck with me this long, is ask you to share the story of your worst date. Make me feel better, people! Give me a reason to LIVE!



Filed under Before Children., Confessions.

21 responses to “The Pretty Boy, The Drunk Cowboy, The A-hole, and The Other Cowboy.

  1. maureen

    my ONE blind date was with my then recent ex. He set me up with his dumb girlfriend’s friend. The guy showed up for dinner IN A SUIT. Instead of acting embarrassed to be over dressed, he agreed that I should change to match him. (I should’ve kicked him out then.) We went to dinner in D.C. and it was deadly boring because HE was DEADLY borrrring. Then we found a cute little bar in Georgetown to continue the dreaded conversation. There was this spunky little old man that got up to dance with some young chic in this stuck up bar in Georgetown. I was delighted with the signs of life while my awful date smirked with distaste and made derogatory remarks about them. O. that was it for me. I said I was ready to go home. I promptly fell asleep in his car on the drive home.

    He told his friend that I was a ‘Dream boat.” I told my ex to make sure he NEVER set me up again!! UGH!!!!!

  2. maureen

    Chi Chi’s!!!

  3. HAaaaaaaaaaaaaaaaaaaa!!! I’m now very curious about the Impotent Soldier and the Cheating, Bomb-Planting Kickboxer. Please write about them, too.

    I guess I’ve been on a couple weird dates, but my VERY FIRST DATE (other than high school dances) was a blind date. Yep, ME! A blind date! So I was in Newspaper class and I for some reason wrote a humor column, edited, and did random other stories. One of those other stories involved two names being drawn out of a hat (one boy, one girl). Then the two would go on a blind date and write about our experience. Of course my stupid name was drawn, and this senior popular editor guy. I was a sophomore and I was not a very cool one. I was gangly and I tripped on things a lot, and I was PETRIFIED. We went to the zoo and wandered around smelling the animals. I mean I had absolutely no idea how to speak to this guy, even though he was really nice. I was probably bright red the whole time, and I was probably wearing Birkenstocks and socks and a huge softball shirt. I blacked out most of the memory.

    • For some reason? You can’t imagine why in the world you would have written a humor column? Girl, you funny.

      • Thanks Sarah – I take your humor praise very seriously, since your blogs make me laugh so much that I have to share bits of them with whomever is in the room with me. Once I was randomly thinking about Thor in the middle of a conversation and I almost died just thinking about it. I don’t know why I was thinking about Thor, but it’s probably something to do with the fact that your writing is the kind that makes people snort milk out of their noses when they think about it in a public situation in which they need to be quiet but they’re still allowed to drink milk.

  4. Jenn

    This is awesome!. My worst date…and yes, this is real. Post high school I went out with a friend of my friend’s DB boyfriend. This boyfriend was an even bigger douche bag than your HS beau. Anyway, he picks me up at home and meets my mom. She politely asks where he’s taking me.
    Him: Court, I gotta clear up a ticket.
    Um, what? So, yes, he took me to court. No dinner, no Pizza Hut. Court. While sitting in the courtroom he proceeded to point out women he’d slept with.
    After court? He wanted to add me to the list. That. did. not. happen.

    • Oh my god. That IS pretty bad. But if he didn’t give you a black eye…or rough you up and then offer you $100, cash to smooth things over, then….I still win for biggest douche bag. Not really a thing I want to win but…

      • Jenn

        Yikes! As big a douche bag as my date was, I was referring to the friend’s BF who set us up being the biggest DB ever. I won’t get into details online but trust me.

  5. Dennis

    Oh man, Sarah. You and I went on dates! I like to look at the bright side so if I lowered the bar so that John could move in and give you all that you have today so be it.
    I’m glad I was able to help.

  6. Mark

    I’d really just like to hear more about your sister, because I sadly missed that stage of her life.

  7. JennJane

    I am speechless. I need your book in my life-so get on that, sister!

  8. olivermcbubbins

    Since I’ve only had about three dates in my life outside of Nancy, I’ll have to go with perhaps my first one. If you can call it a date.

    Really, it was just going to a party with a high school “girlfriend.” We basically went to a room at this guy’s house, didn’t really know what to do, and made out on a tiny bed for HOURS. I can’t imagine it was good for anyone, really. We probably just had wet faces and sanded down privates.

    Afterwards, we were in the kitchen and she took a condom and threw it in the garbage. When I asked the obvious question, she said something about a friend knowing how many she came with and how she wanted me to say that we had sex. Being completely retarded, I obliged.

    Then the guy who’s house we were at proclaimed that we broke the bed. I got made fun of for that for many months before I came clean.

    I’m an idiot.

  9. Marji

    First off, my sister was also a scantily-dressed party girl who drew a ton of attention. AND she was in a bikini contest at — yikes – the Wildcat House. She lost. Got boo-ed even; very sad.

    Secondly, my very worst date was semi-blind set-up…a friend of a friend. I was 18 and worked full days outside at Old Tucson in the summer. Anyway, I can’t even remember Stupid Head’s name. He picked me up at home (my parents’ home) and I knew immediately that he was Stupid – in a social emotional kind of way. He couldn’t complete a sentence without insulting some person he was talking about. Then he couldn’t decide on whether we should go to eat and said outloud, “nah, too expensive.” We ended up at a bowling ally on the other side of town (his side) and I was starving. We walked in and he immediately grabbed my arm and pulled me back to his truck – “I know people in there.” Then we drove around while he mulled over what to do some more and didn’t listen to me at all. I said “Please take me home now.” He said, “ah let’s just pull in here, this should be fun.” — a seedy 2hr. hotel on Miracle Mile!! I was young, stupid, and had a very hard time asserting myself so I followed him into the Adult Shop that was the lobby of the “hotel.” He went to the greasy nasty guy at the desk and said, ” your sign says $20 for 2 hours, but what about for 1 hour”. — “We only rent rooms for 2 hours” — He argued and argued with the guy in a very stupid, awkward, unclever way and then said, “oh never mind, she’s not worth it anyway”. He thought it was a joke. I said, “TAKE ME HOME NOW.” Maybe I should have ran away and called a cab, but not really a good idea on Miracle Mile anyway. The night ended with a silent ride home. ‘Never saw or heard from him again.

    By the way — I have had MANY MANY dates. Some good. A LOT bad. That one was the very worst, but not by much.

  10. I went on a date with a guy when I was in college — a friend of a fraternity brother of a friend. I was a sophomore, and he was a year or two older. He had a car, so he drove us out to Long Beach for dinner. He was nice enough (except for the starting-to-recede hairline), and conversation was flowing pretty well. Then he started telling me this story of the previous year, when he was at a frat party of our friends’ fraternity that I frequented, as well. He said that it was one of the biggest party nights of the year, and there was this girl he thought was super cute, and wanted to go talk to her. He kept trying to approach her, but she’s scuttle off to another side of the room whenever he started getting close. Finally, he caught up to her, touched her arm, and she turned around and yelled, “I’m only 13!!” And guess who had taken her 13 year old sister (who was visiting for Lil’ Siblings weekend) to a frat party the year before because she didn’t want to miss the biggest party night of the year?

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