Search Results: girl's first impression of a guy

This is quite a long story so I'll try to tell it in the short version. I met this guy through mutual friends and we have been hanging out in groups and have been texting each other. Also the first night we met he flirted with me and we spent some time alone together, though nothing happened. Later in our texting conversations he told me about his non-existant love life and hinted that he would like something to happen between us, but since those messages things have been a bit awkward when we meet, though I do catch him looking at me. I first thought he was being shy, but now my friend says that he normally isn't shy around girls (though he hasn't had anything serious for a while now), and that he had a fling with one of his female friends. She also thought he always messes up in his relationships.
I was really surprised by this, because I got a completely different impression of him! Also because we really discussed our feelings and he told me about some of his insecurities and that he felt that he had messed up in the past and was trying to get his life back on track. So now I am thinking, because this guy seems so different to me than the image his friends have of him, is he just messing with me? Or could he still like me and therefore act different when we are alone?
AND what should I do about it? Should I hint to him that I would like to spend time with him?