does he want to be with me or just want to be friend?

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Original Visitor's Question from a 31-40 year old Female
I need some help with a situation at work. This is a long one, so - I'm sorry!
I started working there ( receptionist at a school ) last year, and on my first day, the head master took me into the staff room and told everybody about me.
There was this one man who caught my eye, and he seemed to smile at me, but I thought it must have been somebody else, but no - it was definitely me. Then i looked back and he grinned and chuckled when I gasped... then later on, he came into the office and introduced himself to me. When we shook hands I seemed to fall for him completely, and I couldn't stop gazing into his eyes.
I made friends with another receptionist, who told me he was married, and I was disappointed, but then he got divorced late last year, and I just constantly wanted to hug him because he seemed to be fighting his own personal battles everyday.
I know his wife was abusive, and that he is glad to be out of the marriage, but he has two daughter's with his ex.
Then one day I went to his class room with some forms, and I caught him and one of our colleagues kissing passionately, and he seemed embarrassed and even apologised but I walked away.
Tehn at a team-work course I overheard the man and his girlfriend having sex, and it really upset me, but my friend appeared and screamed, and he popped his head out the door and went bright red as he looked at me, and he seemed to apologise with his eyes.
I have low-self esteem, I know that, and that makes it really hard for me to believe that he likes me, but my friend is constantly saying he does, so with her help, I managed to get up the courage to ask him out to coffee.
He agreed to go out with me and he drove me into town and we had coffee. We chatted about the normal things, like where we were from, and then we chatted about who we went for, and he said the woman had to be attractive to grab his attention, but be a nice person too, and when he said that he got this look in his eye, that, now I look back on it, was as if he was saying just like me.
Then on the way home, he asked why i get all embarrassed a lot, and he asked if it was becuase of low-self esteem. I didn't reply but he got his answer when he looked into my eyes.
I started to cry, and he held my hand, and comforted me, and he said that i wasn't exactly ugly, and i was a great person, so i had no reason to have low self-esteem, and he called me 'darling' and 'sweetie' a few times.
He smiles warmly and winks at me an awful lot, and my friend has said on several occasions that she's seen him checking me out, and she's seen him gazing at me across a room, even when he's been talking to somebody else.

I was just wondering if you thougth that he maybe wanted to be with me, and if you did think that, how I could know for sure without actually asking him, and how to get closer to him with this low-self esteem i have.

User Submitted Advice from a 21-30 year old Female
Baby steps

He might be in the bachelor stage now that his marriage is over,willing to sleep with anyone. Yet he knows you aren't there yet,so is kinda backing away from you. Torn between getting involved in another relationship. But after he burns out...

You should definitely take baby steps,and talk to him bit by bit. Make little plans,and go in ready to attack them. The best card for us is to see how he reacts when you talk to another guy. Do you have a guy friend,or a gay friend? Ask him to step in and monitor his reaction for you. That's how I did it in the past. Guys normally spill to other guys. My NOW boyfriend told my "fake" boyfriend everything,actually threatend him. My guy friend was like,"The guy is crazy about you." He asked him,What he did,told him not to play games with me. Tried to get him to date someone else. Funny,he never realized it was a bait. One point,my FAKE boyfriend was smoothing my hair back. He came up and kinda pushed him out the way. Told me,"It looks better down." I REALLY hope you get him. But most importantly I hope you realize that your humility is your sexiest trait. You're gorgeous,and it's beautiful you don't totally act like it. But show it some times. I hope he deserves you,and that your image of him isn't to big of what he really is..

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