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Quick: attempting one-night stand tonight - August 6th 2018, 08:17 PM

I'll try to make this quick.
I'm trying to hook up with my roommate before she moves out and we never see each other again (in all likelihood). We're going for a drink later and I don't really know what I'm doing. Never have. We're friends, but not that close. Anybody got any advice? Please answer within the next 6 hours.


Wish I lived in Canada. UPDATE, NOV. 9th, 2016: This statement has become even more appropriate.
I vow that I will attack this endeavor with an enthusiasm unknown to mankind. Jim Harbaugh

"Being an adult sucks. The only positives are weed, sex, and cars, and I have none of those right now." -Me

"Darkness cannot drive out darkness; only light can do that. Hatred cannot drive out hatred; only love can do that." -Martin Luther King Jr.
   
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Re: Quick: attempting one-night stand tonight - August 6th 2018, 09:30 PM

I'm fairly sure we're not allowed to give explicit advice about how to go about hooking up with someone on here.

I'm actually kind of wondering about your intentions and why you assume your roommate is interested in having sex with you. I am sure your a perfectly desirable person, but I don't think that her wanting to go for drinks is a for sure sign that she wants anything (far from it, in my opinion). I'd be very careful about how you proceed -- for example, if you wait until she's drunk, she might feel like you took advantage of her inhibitions being lowered and that's never ok. If you lean in assuming she'll want to kiss you, well, as long as she's sober, it's not like you're doing anything wrong but be prepared to be rejected and have to go home and spend the night in a home with someone who might now feel intensely uncomfortable.

I guess you might want to find a way to read the situation and find a way to see if she is equally as interested in hooking up in a way that won't make her feel profoundly uncomfortable and be prepared to be rejected. If you guys aren't that close, I would imagine that her wanting to have sex with you just for the hell of it just cause it's the last time you will see each other isn't all that likely. Though, I am just kind of basing that on the way that I know men vs. women approach sex and I definitely know people who don't exactly adhere to what I would expect, so while this is my thinking, I'm not saying to not try at all, just that, idk, be considerate of the fact she might not be interested in having sex just cause you're desirable and you're there and there's no expectation.

On the other hand, putting your cards out there and letting her know that you'd be interested might not be the biggest deal; as long as you do it in a way that lets her know you're making your self vulnerable and non-threatening, even if she does reject you, you can minimize it being awkward. Just be really careful. If she does consent, it should be with some level of enthusiasm; the last thing I'd think you would want is colouring your guys time living together with the awkward memory of her rejecting you and wondering if you always expected this and questioning her whole time living with you.
   
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Re: Quick: attempting one-night stand tonight - August 6th 2018, 11:42 PM

Oh right, I guess this isn't Reddit... Honestly though, I'm desperate, she talks about how horny she is every now and then, and we're very friendly with each other. That said, we probably won't stay in contact afterwards, and I'm hoping for an attitude like, "one last fling, why not"? She's done it before. And no, I'm definitely going to make sure we're not hammered. In fact, I'll probably give us time to sober up before I do anything.


Wish I lived in Canada. UPDATE, NOV. 9th, 2016: This statement has become even more appropriate.
I vow that I will attack this endeavor with an enthusiasm unknown to mankind. Jim Harbaugh

"Being an adult sucks. The only positives are weed, sex, and cars, and I have none of those right now." -Me

"Darkness cannot drive out darkness; only light can do that. Hatred cannot drive out hatred; only love can do that." -Martin Luther King Jr.
   
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Re: Quick: attempting one-night stand tonight - August 7th 2018, 10:23 PM

Aaaaaaand failed. We only had one hour left, and I hadn't slept in two days. Couldnt have had sex if I wanted to. Moving on...


Wish I lived in Canada. UPDATE, NOV. 9th, 2016: This statement has become even more appropriate.
I vow that I will attack this endeavor with an enthusiasm unknown to mankind. Jim Harbaugh

"Being an adult sucks. The only positives are weed, sex, and cars, and I have none of those right now." -Me

"Darkness cannot drive out darkness; only light can do that. Hatred cannot drive out hatred; only love can do that." -Martin Luther King Jr.
   
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