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I've done the roommate sex thing and it was great, although it's a relationship and if things go bad... it can be a difficult situation. Especially when she's bringing home a different guy each night while you're sleeping alone in the next room listening.
What would I do? Sleep with her. If it doesn't work out, then one of you will move. You'll regret it in the future if you don't explore your feelings with this girl. If possible, try to make it a "friend with benefits" thing and you'll be living a young man's dream. I literally sat on a couch with my roommate one night and we worked out a workable relationship involving sex, and it worked out. Most roommates only stick around together for about 6 months anyway.
Regarding the shyness, you need to work at building up your self-confidence. I found travelling to be the best cure for me although just getting a bit more experienced sexually helps a lot. Sounds like you've got nothing to worry about if girls are checking you out and letting you know you're cute. BELIEVE this and write a new internal dialog in your head that says "girls think I'm good looking and want to go out with me" and repeat this in your head when you feel nervous. Also, just take a chance and see what happens. If you've ever done something scary like riding a rollercoaster, think about that moment just before it starts the first big drop. It's just a moment but can be the best part after it's done although at the time very scary. Enjoy the thrill rather than dreading unknown consequences!
Tell the new girl you're dancing with outright that you're shy and much better one-on-one. This is a great way to slip out of club or set up a date where you can be alone. Just don't take her home and have sex around Jenn. Keep your private life private and sex with Jenn to yourselves.
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