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My 5 Biggest Hook Up Regrets

bathroom.jpgYom Kippur is all about reflection. So, I spent a good portion of yesterday in synagogue reflecting on things I have done over the past year in an effort to clean my slate and ask God for forgiveness. I usually try not to regret those things that I have done, but that is not always possible, especially when alcohol is involved.

1. I regret that time I met a guy at a bar and did some naughty things at a very public table. That other people may have been sitting at. And the bar also happened to be a restaurant. And it was definitely not sanitary.

2. I regret purchasing condoms while drunk and choosing that the ones that glow in the dark/have spikes “for her enjoyment.” I did not enjoy them that night, nor did I enjoy the way those spikes made me feel for the next 3 days.

3. I regret thinking hooking up in a boy’s bathroom was “hot” – it was not. In fact, it was dirty, moldy and didn’t have a lock. So, with that, I regret that guy’s roommates walking in and getting quite a show.

4. I regret hooking up in my roommate’s bed because she then hooked up in my bed in retaliation…and made a much bigger mess.

5. I regret keeping my hot stilettos on during a particularly wild romp that led to a giant gouge in my wall and a large, bloody gash down my man’s back.

I know I am not alone in making poor hook up decisions. What are your biggest regrets?

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13 Comments

  1. Gina says :

    T

  2. Gina says :

    The morning after I lost my virginity, the guy shook hands with his buddy, condom wrapper in hand. In. Front. Of. Me. Now, we were all friends; but come on. How could he have thought that that was appropriate?

    …oh, maybe because he was still a little drunk from the night before.

  3. C says :

    I’m the same way - I try not to regret my past indiscretions. But I was the type of girl who, in high school, couldn’t be bothered with needing a boyfriend attached to my hip all hours of the day. I know some girls needed one for the attention or recognition it brought, others because they genuinely found a nice guy. Anyway, that resulted in a lack of sexual experience, until the end of my senior year when I decided it would be a smart idea to hook up with an Italian man 14 years older than me. All that left me with was an ambiguous state of virginity and a whole lot of regret.

  4. loneboywonder says :

    I regret that time in the alley behind where he worked because he was afraid of seeing me anywhere else in case he got fired.
    I regret that first drunk sloppy sex moment after staying awake until 5am waiting on him to come over for him to finish himself off in a twin bed and then never return my calls.
    I regret those countless headless pics that have probably become internet sensations by now.
    Then there was that time I travelled all the way to the suburbs only to realize that he had a drag queen title and chlamydia. Can you say run away as fast as possible?

    I really should have taken part in yom kippur…

  5. Goody says :

    Um…drunk, bunk bed, beard burn and a guy that kept calling me, “Son”. I left the next morning with bruises in places that sex shouldn’t bruise (sternum? WTF.) and bright red skin covered in hickeys. Oh yeah, and a limp because I fell on the way down the bed and bruised the shit out of my shins.

  6. Heather says :

    hahahaha… son.

  7. funfun says :

    oh god…i didnt even need yom kippur to repent my worst hook ups from the past year.

    how about the time I woke up at 5 in the morning had no idea where i was but knew i slept with some random guy..didnt know til 4:00pm that day who i had slept with :/
    or that time i wet his bed after

    good thing yom kippur was on my birthday and spent the day fasting and in temple

  8. DZ says :

    the chick that squirted a shit load on the floor, i slipped on it and hit my head on my lamp

  9. Mia says :

    The time we hooked up in the stairwell on my period. Smearing the souvenirs of our sex (his and mine) in dirty hand print on the stairwell wall.

  10. Jen says :

    Uncontrollable, 3 minute long queef. Laughing only makes it worse.

    I HATE QUEEFS

  11. TrishaEstra UTAUSTIN says :

    The time when my boyfriend and I were at his house and getting it on in his pool everything was going great till his 18 year old daughter made a surprise visit. She got an eye full it was the most embarrasing moment! what is even worst is that she goes to the same university as I and I bump into her quite often!

  12. GirlFriday says :

    HAHAHA 3 minute queef! That’s hilarious! But yeah, I hate queefs too ;)

    My biggest regret at the moment is hooking up with a friend of mine a few months ago. We were both so drunk. And it turned out he was a virgin. It was so bad that I’m not even sure what we did could be considered sex. He just laid there with a look of shock on his face while I humped him from on top. And his d*ck was the smallest I’ve ever had. Needless to say, it was not a very satisfying evening.

  13. Hellbean says :

    I regret falling in love with a practically-married man 16years older than me and still accepting being the mistress 8 months on.

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