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[quote=Anonymous]My DH struck up a friendship with a co-worker that started exactly like this.  He talked about her a lot, did lunches/etc at work.  Yes, he was always home (we lived further out then and he took the VRE).  But it just seemed to cross a line.  I told him I was uncomfortable, and his response was to keep their actions a secret from me.  I learned that part when I stumbled onto something about 6 months after our first convo.  Only then did he break it off.  I do believe him that things never got physical, which is how we managed to get past it.

Anyway, here is what I see as red flags: 
1)  It seems to be an excessive amount of time for helping someone find a job.
2)  "You're hilarious" could be getting too personal.  It could be a sarcastic response, "no, bad idea for a job", but it could also be much more.  OP needs more info on how often and what topics they discuss.
3)  It seems to be very separate from OP.

But a good sign is that he wasn't concerned about OP seeing his phone.

OP, you just need to have a talk with him.  Discuss what you each feel is appropriate parameters for friendships with the opposite sex.  For all you know, he could be feeling a little uncomfortable himself, especially if she's the one initiating contact.
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