Been hanging out with this amazing woman for a couple of years(not sexual, I'm dating someone I really like, this is just a friend). She is a BLAST! Funny, smart, Hot, quick witted, all around fun to know. My girlfriend likes her, my friends like her, she is the bomb and shite.

Anyway, my buddy is really into her and has a HUGE crush going on. Cool. I think they make a good match. He is smart and funny, but socially awkward and sorta a derp. She is socially queen god damn bee, everyone loves this chick, but she has made it clear to me she is interested in him, wherein lies the problem....

I could easily fix them up, both trust me and look to me for advice often (scary, but true) BUT....

She is sort of a "free spirit" as in, she has been naked with a LOT of guys. He is sort of a "virgin", only 2 or 3 women I know of he has slept with. He is also pretty much a prude.

So, I could get my friends laid (both of them, with each other) and hope for the best, or I could warn them away from each other and keep the guy from getting all butthurt and crazy when she doesn't instantly want to marry him (as he is absolutely going to want to do if they sleep with each other), or I could just stay the hell out of it, but what fun is that?

I suck as a sensei.

I'd personally stay out of it. They are adults, either it will work out between them on their own or it won't.

 

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I won't give advice but a prude and a free spirit can lead to the hottest sex

Sexual chemistry is unpredictable and so I'd drop that concern

 

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I suggest to you the magic of drunk fu.

Then your part is done, and you stay out of it.

 

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4 some obviously

 

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It sounds like the groundwork is already there. Ask them if they would like to double-date or just tell your friend to stop pussyfooting around and take the plunge.

 

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Why not just tell the truth and let the dice fall where they may?

 

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Reason I'm asking is there is a party at my house tonight, only about 30 people coming, all fairly close friends. Everyone is supposed to crash here afterward (no drunk driving for my friends), then we get up to a great breakfast cooked by this couple who make the best biscuits and gravy in the universe.....

Had a lot of these parties since I moved here. Always end up being fun as hell. Sleeping arrangements can be somewhat difficult however. I don't have 30 bedrooms after all, or even 15. People have to share. I usually can figure out a private room for all the known couples plus a few left over, and set up at least a private bed for all the singles, though sharing a room with other singles....

I could set it up so these two are almost assured to be alone in bed (solo) in a room with no one but them, or I could set it up so they are in rooms with other people who probably aren't there, as they are "secretly" visiting other people. Yeah, lots of sex going on, whatever...everyone is an adult and aware of whats happening.

I'm pretty sure the match up wont last for long, much as I love both these people, much as I wish it would take....I just don't think it will, he is way too uptight, she is way too non-uptight. I don't think it would be a bad thing for either of them, in the long run, to experience it though, and they might just make it. Be awesome if they did.

God I'm old. Why the hell am I thinking about this crap? Shite happens.....sorry.

Well you could always go by Oscar Wilde in this case.

 

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