Was I stupid or just cruel when I was young?


July 14, 1996

Maureen invited me over for my birthday. She baked a cake, bought the new Ramones CD for me [Note: Greatest Hits Live] and gave me a card. Then she took me out to dinner, which is very sweet when you consider she doesn’t have a pot to piss in. Then she took me to her friend Stephanie’s party, where I met Eve. Eve is pretty and aggressive. Pretty aggressive. Very charming. Petite with a bright smile. Have I mentioned she’s pretty? I didn’t ignore her but I didn’t overtly flirt with her, either. It was a tiny, packed apartment and at one point, Eve brushed past me and I felt her hand slide into my pocket. I thought she took something out but she didn’t. She put something in. A slip of paper with her phone number on it.

Let me think for a minute and try to recall how many times I’ve been to a crowded party where a pretty girl jammed her phone number into my pocket.

…   …   …   …

Okay, NONE. Zero. Nil. Never. The empty set. So I called her on Monday and arranged to meet for drinks on Friday, to which she promptly and happily agreed. By Wednesday, this had somehow gotten back to Maureen. She called and beat the shit out of me with the old ‘How can you do this to me?’ one-two combination to the kidneys and solar plexus. Then she gave me the ‘I’m humiliated’ upper-cut haymaker and I was down for the long count. After I got up off the canvas, I immediately went into begging mode which, let’s face it, is the only thing in life I’ve perfected. It’s a shame I can’t monetize begging.

I was tripping all over my words with apologies for my transgression. The next day, as part of my penance, I called Eve and cancelled our date. When she asked why, I couldn’t come up with a sensible reason. I forgot to rehearse one. I said, “Well, because Maureen is quite upset,” which makes me sound like a fucking noodle since Maureen is NOT MY GIRLFRIEND. Eve said that Maureen is just jealous, which sounds logical to me.

I subsequently wrote a befuddled letter of apology/explanation to Eve which she should get either today or tomorrow. We’ll see what kind of response I get, if any. [Note: This is how it was done before the internet was invented, kids.] It seems that fate tosses a potential date in my path about every six months. If Eve counts as this cycle’s allocation, I won’t meet another girl until well into 1997.

Pouring over these journals reminded me of this post. It’s a bit crass but I love it.

* * *

When I think back, the breadth of my cluelessness regarding the sweet science of love is almost too astonishing to be believed. I was awful at it. I knew nothing. The group of guys I hung out with weren’t popular with the ladies, so there were never any discussions about seduction or technique. It was a slow, painful, embarrassing learning curve.

For a good long while, I thought you got a girl to sleep with you through insistent pleading. I thought the game of love was to wear down her resolve until she finally capitulated. Imagine my surprise when I discovered that haranguing was not considered a legitimate aspect of a foreplay. I remained in my clueless state for a number of years. I failed to recognize a lot of green lights and opportunities. I was unaware of how many women were willing to sleep with me. But I realize it now.

* * *

The first time I had sex, she said, “Go ahead. You can do it.” But the DIRTY DEED had already been DONE. Admittedly, an inauspicious debut.

The first girl I slept with had the temperament of a sea monster.

* * *

With my first regular love, I used condoms that were about as thick as a garden hose. I didn’t know anything about lamb skins or sensitivity. I was mortified that I had to buy them at all. I just wanted to get in and out of the drugstore as quickly as possible without asking (or being asked) any questions.

The condoms robbed me of all sensation. So much so, that I often couldn’t finish. I would occasionally pull the damn thing off and toss it across the room just so I could finally complete my mission. In retrospect, a terrible idea. When I think of all the unprotected sex I had, it’s a miracle I never had to deal with an unwanted pregnancy. Or worse.

* * *

I read an article by a woman who said her boyfriend was so emotionally overwhelmed by sex that he routinely wept afterwards. She found this romantic and touching. So the next time I slept with my girlfriend, I tried to cry but my heart just wasn’t in it. It sounded like fake, ridiculous, insincere blubbering. My girlfriend asked if I was having some kind of breakdown.

* * *

Once upon a time, I was making out with a girl. I got up and put a Kenny G album on. I didn’t like the guy’s music but I thought it would be romantic. That’s what I’d read somewhere. About two songs in, she stopped kissing me, sat up and yelled, “My God! Would you PLEASE turn that OFF!”

* * *

I faked an orgasm once. The sex was tedious and went on far longer than it should have, so I decided to end it by faking an orgasm. I believe she was equally relieved it was over.

* * *

They weren’t all bad experiences. Many years ago, on a warm summer night, I made beautiful amour in a rooftop garden atop a downtown Brooklyn brownstone with the twinkling nighttime Manhattan skyline at our feet. It looked like a magical movie backdrop.

It’s time to bid a fond farewell to the holiday season. Only 11 months until Christmas!

Harry Winston on 5th Avenue all gussied-up for the holidays



85 thoughts on “Was I stupid or just cruel when I was young?

  1. ” I tried to cry but my heart just wasn’t in it. It sounded like fake, ridiculous, insincere blubbering. My girlfriend asked if me I was having some kind of breakdown.”

    I just nearly choked on my breakfast due to a bubble of laughter.

  2. Well, at least you called it off which quite honestly I wasn’t expecting. If only it hadn’t got back to Maureen… Guilt is a bastard at ruining possibilities.
    Well? Did Eve respond to your letter and HEY! where’s the letter? I wanna read it. I want to know how you handled it. Spoilsport.

    Let me tell you straight: A girl doesn’t want you blubbering after a steamy sex session. Romantic you can be but a wussy cry baby not. Woman wants man. Ug.

    Love these journals of yours.

    • That’s the worst possible position to be in: too clueless to know I’m being offensive but enough of a human being to not enjoy the fruits of my misstep. I don’t recall ever dating Eve. Further excavating in my journal might reveal otherwise. I’d like to read that letter, too. What could I possibly have offered up?

  3. Another excellent extract. Not fair of Maureen to do that though when she wasn’t your girlfriend! If only guys knew during those early exploits how nervous and humiliated girls feel too they might cope better – us girls do know that guys go through it too so we have the upper hand from the start 🙂

    • I don’t fault her. She liked me. That’s not a sin. It’s rather unfortunate, actually. And, please. During the early exploits I knew NOTHING. About me. About girls. About life. I caught on eventually but not without leaving a trail of broken hearts in my wake. Most of them mine.

    • I told her on many occasions that it wasn’t ever going to happen but that made her resolve even stronger. I’ve done that, too. We all want what we can’t have and what’s available to us isn’t that interesting.

      • I’m so glad you kept the evidence. The rest of us burned it!

        And I answer to your question, I vote both. We all were. But I swear it was easier to accept rejection when the guy was cruel than when he was nice …

      • I am constantly wrestling with whether or not I should burn these. CONSTANTLY. There’s a lot of stuff that will never see the light of day and I don’t want my daughters reading. I have to destroy them before I’m gone. But when?

      • On your 80th birthday. Or if you (God forbid) get really nasty medical news. Or if you need to burn your house down for the insurance money. Or when you win the $1.5 b because that is too much blackmail fodder.

  4. Well, by luck or judgement you did well in telling Eve the truth about why you cancelled the date. She couldn’t fault you for being sensitive to the feelings of another woman, and at the same she knew your loins were in still the right place for her. Did she give you another chance?

    • Bull. Shit. Eve was hot. I should’ve charged ahead with wreckless abandon. That would’ve been a more satisfying memory. I don’t recall ever dating her but I need to read on in my journals. I could’ve and forgotten about it.

  5. If it’s any consolation, you are touching on, how to say, some universal themes here.
    I don’t know which amused me more, the hand-in-the-pocket tally or “monetize,” even back then.
    Thank you for making me think about all my sexual embarrassments this morning.

  6. Yes, you brought some of my own tragic memories back too. ‘Preciate it. I’ve been so happy lately, but now…

    I almost blew it with my wife when we were dating by not reading her signals correctly. She says she was “throwing herself” at me but I was playing it way too cool. Didn’t want to seem like a cave man or something. Luckily fate intervened.

    Your misfortunes did make me laugh a few times. Sorry about that…

    • Glad I could oblige. Misery loves company. Have you heard? You don’t need to apologize for laughing. That’s why I put it out there. Plus, I wound up with a great wife. Now I can laugh, but it wasn’t very funny at the time.

      I wish I could claim that I was playing it cool but in retrospect, I really don’t think I had a clue. I was so consumed with low self esteem that I couldn’t imagine any girl wanting to have a conversation with me, much less take me to her bed. I demand a do-over!

  7. It’s a pretty safe bet that a lot of women would have similar tales of their early forays into the minefield that young love can be.
    If dementia overtakes me and all I can recall is my miserable non-dates…

    • If you’ve got stories to tell, lay them out there. I’ve thrown down the gauntlet.

      I wouldn’t have felt so bad at the time had I known all these horrific episodes would one day make for a decent blog post. See that…I made something from nothing.

  8. That was funny set of techniques — but all totally understandable.

    I still can’t think of more than one or perhaps two times in my entire life (51 now) when women have made plays for me. It’s boring after a bit, having to be the one that does the chasing all the time. I remember back in 2007 when Seriouscrush showed that she found me desirable in a way which even an idiot like myself could not fail to see, that I was absolutely stunned. It took me months to accept that she wasn’t faking it.

    That’s why I like internet dating — you’re instantly over a lot of the hurdles that led one into scrapes like those you describe and for all the way that it feels like dating in a lunatic asylum, it’s a more straightforward way of conducting one’s affairs.

    • I didn’t have to approve this comment. Do you know how happy that makes me? I hate when WordPress jerks you around.

      Imagine guys like Leonardo DiCaprio of Bradley Cooper who are constantly and relentlessly chased by women. I wonder what that’s like? I wonder if they complain about it in private? Naaaaa. What am I, nuts? Of course they don’t hate it. Who would hate all that adulation? I liked it very much the one time it happened to me.

      I only WISH they’d invented internet dating sooner. I wouldn’t have had to wait every 4-6 months to meet someone to go out with. More like every 4-6 hours. I remember when people first started internet dating and how the popular consensus was the only a lunatic would meet a total stranger off the internet. It’s quite common now. You lucky ducks.

  9. Hurrah for that. WP will one day join the rest of us in the 21st century.

    4-6 months??? My dates were measured in years apart! Thank the Lord for the internet — I think I had four dates in 2015, which is really good going. And enough, actually.

  10. How come when some people write about their past experiences, it’s always with a view towards somehow sugar-coating something (like a challenging experience, for example) to explain how awesome they are, but you never do that? I like that you’re honest, which is why I read you, and that you don’t self-romanticize.

    The Eve thing – you should have gone out with her. The sex stuff? I think you’ve hit on some universal experiences here. I feel that I really shouldn’t elaborate on that (I’m shy that way).

    • Hi, Trent. Nice to see you. I keep it real, baby. No sugar-coated horseshit from me. Growing up was a series of compounded failures for me. Something tells me these tales feel strangely familiar to a lot of folks out there, although they’re probably not willing to put them out in the public domain.

      I didn’t see Eve because I can’t stand the thought that I’ve hurt someone’s feelings and will do whatever it takes to make amends. Admittedly, that’s no way to go through life.

  11. Ah, you are a much better man than I, i was a right bastard in my youth, i would have straight away asked Maureen if she was so pissed then why not fuck me and at least have a claim, i then would have got her in the sack on Thursday and been out with Eve on Friday (hoping to do the same with her), someday i’ll get to that on the Lounge, a whole series of escapades with the fairer sex but for now i’ll enjoy yours…

    That second half is pure comedy, i also thank my lucky stars that i have lucked out and had no unwanted pregnancies or worse in my wayward youth, sometimes i wonder if someday they’ll be a knock and some twenty-something will be standing on my porch saying, “Hi Dad.”

      • Us weirdos have that tendency Mr. Looby, you also have the best title i’ve ever seen for a blog (sorry Exile yours is damn good as well), and i’d have to say both you and Exile are right, i was a bit of a shark i guess in my youth but i also found being unconservative and curious went a long way with the ladies or at least the ones i chased or was around, i have on old post called the Marriage Proposal i think you’d like, it involves acid and cunnilingus… it’s old as well, maybe 2010?

    • Maureen was more than willing to give up her cookies but I had no interest. She was nice enough to talk to and I enjoyed the time I spent but when I sat across the table from her I felt no boiling in my loins. Nothing! I don’t recall ever seeing Eve again but my journals might have something to say about that.

      • You think i understand this technological shit maaaaan, i gotz no clue how to fucking link shit, i believe it’s why i’m often referred to as a Luddite.

  12. Thanks for the insight into your dating/love life history. Interesting reading, as always.

    It never occurred to me that guys were nervous and inept and clueless, too. I mean, on an intellectual level I knew that. but at the gut level it seemed like we, the females, were cattle milling around in the pen, just waiting for the auction to begin and – please, dating gods – let somebody bid on me.

    This analogy breaks down if we contemplate the implications for udders, and that bid cattle are led to slaughter. Or it gets more interesting.

    • Guys AREN’T nervous, inept and clueless. *I* was but typically, guys aren’t. My witches brew of fear, self esteem issues and lack of usable information made me a special case. I know that cattle feeling all too well. Udders, on the other hand are a mystery to me. Thanks for readin’ and writin’.

  13. You made this fan of yours a bit uneasy with your candor, but also feeling less alone with her own awkward moments… I think everyone can relate to this. You seem to own personal revelation in the sphere now, Mark! What else can you unearth for us?!

    • I worked a little blue this time and I probably should’ve posted a warning but that would’ve spoiled the fun surprise. I can assure you that that’s the limit of my personal revelations. I won’t discuss anything contemporary. Just this long-past history stuff is appropriate.

      • I appreciate that but “real” is a relative term. Some of what I do—especially this post—is a bit too much reality for some. Who needs to hear about my early failures?! No matter. I throw it all out there and hope it’s received in good faith.

  14. Yeah Mark, yours is a match here on a floor of dry hay for the rest of us, and all our memories that are not much different than yours, which is why as Ross mentioned, they are universal…
    We’ve been in London now since last Friday and yes, it’s remarkable as you know and more so than I remembered, haven’t been since 98, foolishly thought I’d seen it and didn’t need to go back, and now I feel I could stay, for sure. We’re seeing plays, riding the tour bus, walking a lot, good weather. My writing is focused on prying out a piece of fiction with a bunch of memoir hidden inside (razors in apples) and it feels good to focus on something that seems more real than this blogoni here. But enough about me, here in your apartment. Enjoy the day, thanks for making me laugh and think, and feel some…. Bill

    • It’s a comfort to know I’m not the only one who had a series of failures before I got it all sorted out. Well done on the match/hay metaphor. Nicely stated.

      Good weather can make or break a trip to a place like London. You need to get out and see it on foot. That’s the only way and it’s no fun in the gloom. London is superior to New York in it’s geography. NYC is all concrete whereby London is a series of charming neighborhoods with a surprising amount of green. At least..that’s how I found it. Wish I was typing this from London right now instead of New Jersey. Looking forward to the posts.

  15. So you never went out with the girl that stuffed the phone number in your pocket? The other one obviously had a thing for you, but that doesn’t mean you can’t date the women around her. But I guess I remember those days when everything was complicated like that.

    You were swimming through a sea of endless poon back that. I am in awe of you, brother.

    • My friend, the only thing I was swimming in was frustration and blue balls. I was always on the hunt but I rarely landed my prey. The city was full of women who thought I was a nice enough bloke, but getting involved with me romantically was out of the question for some reason. Even a blind squirrel finds a nut every once in a while and someone would favor me, but there were long, long dry spells. There ain’t much to be in awe of. Trust me.

  16. Sorry I missed this post, Mark. I didn’t see it! I’m so glad I read it. It’s very entertaining. How’s that book coming? I like how Eve slipped a note in your pocket. Who does that anymore? Think how the younger generations will never experience this type of thrill? This is why you must write this in a book. Do it! Thanks for sharing all your awkward moments with us. I found your starting point interesting – not talking about seduction and techniques, etc. It made me think everyone comes from a different angle when you start out. I’m not sure what mine was…I’ll have to think about it. Mine was probably the opposite – that I had to seduce. Fascinating.

  17. I’m finally out and about again, catching up – and this post, THIS POST, just cracked me up! And made me a little sad… I’ve been Maureen, and I’ve been Eve. And I’ve been you… I will point out one obvious point that others apparently didn’t notice/comment upon: How the fuck do you think Maureen “caught wind” of your planned date with Eve? Hellooooo? Eve made DAMN SURE she knew… games, my dear… all the fucking games… you were better off skipping ahead to the next gig… although throwing Eve a bone wouldn’t have hurt anything (and I know you see what I did there…)

    As for dodging the unwanted pregnancy? Another clue for you, good sir… “That you know of…” Happened/happens all the time that an unintended pregnancy occurs with casual, unprotected sex, and the lady will simply end it, never telling the sperm donor. Sorry to barge in with a blast of reality, but that’s the facts, jack…

    • Guess what? *I’VE* been Maureen and Eve, too! I think we all have, which is why everyone enjoyed this post so much. We all have these common, slender threads binding us through shared experiences.

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