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I'd say one way to approach it might be to up the ante and flirt with her a bit and see what happens. Get the convo to a point where you can say something like, "i can't believe we're not dating already" and it can be written off as a joke.
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If you look at the big picture, if he went in his cave 5 times in 2 years that's on average a 1 week cave time each 4.8 months. Which is more than reasonable. Can't you give him that? During that week just do something else.
It's the same with me, I want to meet a great girl and have my next relationship hopefully be my last. Anything else, assuming you don't get children out of it, seems like a waste of time. Like this past few months I've been seeing a girl, spending lots of money dating her, doing fun things, and then she dumped me by text. So I'm back at square one, except with less money.
I had a friend tell me his friend has slept with 3 girls off there. You just use it late at night around all the bars (chicago) and they will meet you out at the bars and it eventually ends in sex.
Are you cute? Not that it even matters. Guys will want to hold your hand, butt, and everything else. You not having experience is something many men will find cute, sexy even.
Let me know what you decide to do and what happens.
I've heard chewing on ice.