I am really confused with whether my boss is flirting with me or just being friendly:
He winks at me
He walks past me, looks me in the eye and then smiles
I passed him a recept the other day and he practically took my hand with it (Slid his hand down my hand)as he looked me in the eye and said "Thanks Skyla"
Walked past me the other day and quickly dragged hus hand across my shoulder
Another co-worker who my boss has been friends with for a long time said my boss told her he cares a lot about me
Asked me to come up to his office and had a huge chat with me about random things like if I use protection, what would I do if I got pregnant, What I do in my spare time, Would I like more responsibilities with my job? Is everythign all right?
Said when they sell the business one day that they are taking me with them
Always commenting me, saying I'm a bloody good worker.
Whne I went on holiday, he told me to be naughty but be careful.

Sooo is he flirting?

Yes, he is flirting and, at least here in the US, he is committing sexual harassment. Your boss has no right to ask you if you are using protection, pregnancy, etc. IT IS NONE OF HIS BUSINESS!!

Yes he's flirting big time. If your cool with this then by all means be careful, in office relationships are usually not the best idea and can lead to "scandals" or best case you break up and it's a really uncomfortable working environment.

If your not OK with this, let him know! Politely tell him that either your not comfortable or give a little white lie and tell him that your boyfriend wouldn't approve. If the harassment continues though you need to talk to his superiors about it. You can remain anonymous in doing so too. If he is the head guy and your really uncomfortable with his advancements I would suggest another job.

Is this guy married by any chance?

I got two words for you, "SEXUAL HARRASSMENT"!!

p.s.
And to those of you whom know me
Yes I know I shouted then.

Hello.

It does sound like he has crossed the line in many ways. As a boss he can care for his employees and want them to be safe but when you add that to holding hands and the deep looks I would say he is flirting with you. He might not act on it, he could be just feeding his own ego but in any case it is wrong of him to do.

If you still feel comfortable working for him then the next time he tries to hold your hand pull it away so he knows your not offering him your hand. That's a quick way to put him in his place without confronting him. If he keeps it up then its time to put him in his place.

Dennis777