Did I come across as needy and if so, how do I redeem myself, I would really like to get to know this guy bett

A few months ago these guys walk into my dept at work - I am mid management so I was curious and just watched for a while - they acted like they owned the place. One of them - we will call him S - walks up to me and says "ok, your turn" and we go in my office and he drills me with questions about what I do. Then he starts telling me he just moved here a year ago and doesn't know the good places to hang out, asks if I know any - I told him a few places to go, he happens to mention that he has a truck and a sports car, then gives me his card - this guy is like my boss' boss' boss, pretty high up on the food chain and VERY focused on his career. Some time goes by and I find myself in a meeting with him, he starts emailing me and flirting during the meeting, just short and sweet type stuff. A few weeks go by again and I email him asking for new work equipment for my staff to increase productivity, he asks the right people for help but nothing came of it - I was a little flirty in the way I asked - that's just kind of how we get along. Then he starts emailing me at random flirting with me once in a while. Then the emails get a little more frequent, I asked for help on another thing but for someone else. He helps, then, he gives me his cell number in an email, one day we were flirting via email all day and he is coming across super strong. Then he calls me, but I was away from my desk, he sent me 5 emails, called and left 2 voice mails, and texted me saying "show me some sign of life, are you there, sorry I missed you... I text him from my car on my way to the gym telling him I was off to a workout class can't talk now, he calls immediately - even though he said he was on a conf. call. We talk for a while, just joking around, and I tell him I have to go or I will be late, he was obviously quite annoyed by that but let me go. Earlier in the week he kept me on the phone flirting with me for 45 minutes, even after I said I had to go work for my paycheck he wouldn't let me off the phone. Well, as it turns out my boss HATES this guy, the 2 of them have this power struggle thing going on, and that thing I asked him to do for a friend of mine - which was nothing more than put her on a committee she belonged on, he did it and it pissed my boss off, then S changed some things around, I asked him to work WITH this woman because she knows her stuff. He did, he made it right, I told him "you are a good man Charlie Brown". But then it blew up in my face a bit and I started to feel like I would get in trouble with my boss, so I text him one night and say "I am sorry I asked you about work, I won't talk to you about work anymore, its none of my business and I shouldn't be involved. S: nothing will happen because you talked to me I promise! Thank you for your help, you helped me more than you know. Next day I send a sexual innuendo text that was OBV a joke, he replied, but I had a bad day and wasn't inthe mood by then, so I didn't reply as I should have.

Updates:
Side note - my boss is a total pig and not well liked by many people in my company. Him and I have had our issues, and I have told S about these issues. Each time I tell him about it he gets his feathers all ruffled up and starts telling me what I should do - I think its cute the way he tries to stick up for me without actually mentioning me.
 

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  • I don't see anything in what you describe as coming off as needy. Nor does it seem like he has lost interest in you somehow. I would suggest that you be careful in talking about your boss to him. That will put you in the middle of their power struggle. It might also look to others like your interest in him contains an element of ambition. Better to just keep clear of those kinds of things. If S leaves then you might be extremely vulnerable with your boss.

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