Should I YOLO it and kiss him or wait?

I've been working with this guy for about five months now, and we're already pretty close. We get scheduled to work together a lot and we talk about anything and everything all the time. If you want I'll give you all the details, but just trust me on this, he likes me. He's always flirting with me, and asking me risque questions, and we get pretty personal. But the thing is, he says that he isn't ready for a relationship. He told me what happened with his ex and it seems like he still is hurt from the breakup that happened months before we even met. So my question is, should I just go for it and kiss him when the timing feels right, or should I "wait" for him to be ready?

I feel like if I make a move that he might think differently about us. Like maybe he just needs that little nudge? I don't know. You tell me what you think. Should I make a move or wait for him to?
Should I YOLO it and kiss him or wait?
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