I was talking to this one guy on OKCupid, actually writing lengthy replies as he was and enjoying the whole conversation, so I gave him my number in hopes he and I would text often, and maybe meet up. However, when he did text me, we only exchanged a few short messages and he stopped. I thought it was a loss of interest on his part, so I went on my merry way of just being and enjoying myself as I was, single or no. Then today, I saw he had visited my profile yesterday, as if reminiscing about our conversation, but being too "shy"
as his profile states he is, to really reach out to me anymore.

Is this the case? Should I reach out to him again? Or is he pretty much a no go at this point?

In the meantime, a second guy "liked" me, a really attractive guy, at least he is attractive in 2/3 of his profile pictures, and so I "liked" him back. I'm trying a new approach where I'm more "aloof", so to speak. Not as upfront, eager and bold. Basically, I'm letting the guy reach out to me, and then going from there. I figure my being bold and upfront, was a turnoff or something. That's what I figured out went wrong on my last date. I showed up in a nice dress, with makeup done and hair all down and flowy, and made sure to make the guy feel that I was interested, attracted and whatnot. Maybe it was too much interest on my part? Besides, we just didn't click the way I wanted to anyways.

Or am I thinking too much about this? Should I just send off messages to both these guys and see where things go?

Why is dating so utterly complex and vexing?