True indeed. Thats usually what I would do take it slowly get to know her heart and mind what makes her tick, start as friends then progress up the ladder. But then as you said she dates an asshole or complains, my hypothesis is that she is too scared to ask you out and thinks that she may get rejected or it's because some nice guys have low sexual.confidence. The title reminds me of a song called Nice Guys Finish Last.

Loverlee your friends dated her ex boyfriend beacuse he was someone who probably had a high sexual confidence and was someone she couldn't have and he didn't go around trying to get her attention. This is possibly why she went out with him. Plus females like to test us males to see if we are worthy for them it's a mechanism they've developed through out thier evolution. P.S this what I have reshearched.