My 5 Biggest Hook Up Regrets

October 10, 2008     Posted in HaHa, Sex

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.


By Noa

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?

17 Comments on "My 5 Biggest Hook Up Regrets"

  1. Gina says:
    Sun, 12th Oct 20084:41 am 

    T

  2. Gina says:
    Sun, 12th Oct 20084:43 am 

    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:
    Sun, 12th Oct 20087:15 pm 

    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:
    Mon, 13th Oct 20087:07 am 

    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:
    Tue, 14th Oct 20081:08 pm 

    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:
    Wed, 15th Oct 200811:28 am 

    hahahaha… son.

  7. funfun says:
    Wed, 15th Oct 20085:44 pm 

    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:
    Thu, 16th Oct 200811:38 am 

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

  9. Mia says:
    Sat, 18th Oct 20087:55 am 

    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:
    Sat, 18th Oct 20088:25 am 

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

    I HATE QUEEFS

  11. TrishaEstra UTAUSTIN says:
    Sat, 18th Oct 200810:08 am 

    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:
    Tue, 21st Oct 200812:19 am 

    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:
    Wed, 22nd Oct 20082:30 am 

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

  14. T says:
    Thu, 19th Feb 20095:54 am 

    Word to hellbean.

  15. Tyler says:
    Tue, 8th Sep 200910:12 am 

    Thank you all for your postings!

    I recently hooked up w/ someone waaaaay too old for me, who was so unattractive that, in addition to inducing slight nausea right now, it made me recall a line from 'coyote ugly' (which was a terrible movie if I remember correctly, except for Adam Garcia, of course), that I hadn't thought of since i saw it 9 years ago: ""Coyote ugly" refers to the feeling of waking up after a one-night stand, and discovering that your arm is underneath someone who is so physically repulsive that you would gladly gnaw it off without waking the person just so you can get away without being discovered. Coyotes are known to gnaw off limbs if they are stuck in a trap in order to facilitate escape."

    I did it partly because I didn't want to hurt his feelings by rejecting his advances, and partly b/c drunk and horny while wearing beer goggles won out, so i made the brilliant compromise of letting him go down on me. Neither one of us finished (it wasn't even good head); I got the spins, and had to vomit. All of that would have been somewhat tolerable if he had at least turned out to be a nice guy, but the worst part is; he lied and told all my friends that we had alllllll sorts of debauched sex, complete w/ detailing lies! Seriously? wtf?! And it's all my fault b/c a) i "didnt want to hurt his feelings?" (I'm sooo stupid) and b) b/c of being as drunk as i was.

    I know i'm going to kick myself for this for a long time b/c that's what i do to myself. But i do feel a little bit better to know that I'm not the only one who regrets a STUPID decision made while shitfaced. So, again; thanks to everyone who posted! This was an awesome idea for a thread.

  16. Vmw says:
    Tue, 17th May 20112:56 am 

    Was that your only time keeping stilettos on during sex, or do you normally wear heels in bed? ( ps. I love it when women do that!, particularly if its heels they wore out to the club/bar/town to begin with !)

  17. Kelly says:
    Sun, 22nd Jan 20129:50 pm 

    I regret cheating on my boyfriend of 2 years with a guy I knew for two weeks (from school). We hooked up in the back seats of his jeep, the same night he told me he was a virgin. He came after seriously under two minutes, I didn’t even have time to fake it. Then he pulled out and CAME ON ME. I didn’t know why he pulled out so quickly till I saw him cumming. Ew. He didn’t even wear a condom.

    I told my boyfriend a few hours later how much I regretted it. My boyfriend and I are still together, and it’s awkward seeing the other guy around school

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