Friendship first........... then make it a relationship, it's a tricky one......lots of people myself included can fall straight into a relationship before any attempt at being great friends is made and established.
It's rare to find someone who you fancy and can get on with so well.. and for them to feel the same way back..someone you can loose hrs in talking rubbish with them, mess about as mates and then sleep with each other...a bit like trying bikes, there's many out there but unless you demo some you may never find the perfect one for you, but unlike bikes, women have feelings too and they need to feel the same way about you, if not...it's not meant to be and life goes on.
Stop putting pressure on yourself to find 'THE ONE' chances are she/he'll come along when you least expect it, when you're relaxed happy and having fun just being you.
So get out there and get demo'ing... take em out, thrash em hard, if it all feels a little wrong, chances are is it and you need to try another!
Having said all that, with a failed marriage, very few relationships and shonky singlespeed what do i know.
I've demo'd a lot and and right now i'm happy with what i'm riding.
BTW, all women have issues and so believe it or not do us men it's how you deal with them that matters.
Just enjoy the ride, don't waste time.... lifes too short!