Why are guys so confusing?

Last year I began talking to an 'old' friend on Facebook, after no contact in almost five years. I met him when at sixth form, he was in the year above me. Anyway I noticed he was on Facebook and decided to say hi, not expecting him to reply, but he did, we had a massive catch up and we even met up in town, which was great fun, and the first real time we spent time 'alone' together without friends around. It was like old times, we had a laugh and it hardly felt like it had been five years since we last saw each other. Since the first meet up (last July) we have met up serval times, and have even gone to London. We text each other quite a bit and I feel like there is quite a bit of flirting between us both. However, over the year I feel like some of the things which have come up in conversation- texts and/or in person have come across as hints that he likes me, I know he had a bad break up with his last relationship (who he was with when at sixth form) which I think may have effected the way he now feels about starting a new relationship, and is dropping slight hints, I have spoken to my best friend about this and she also thinks he's hinting. we have got so many things in common it's unreal, and get on hilariously well. I love his personality, he's caring and is always happy to help. And is happy to go out of his way to please others. when ever we meet up, he always offers to pay for food and drinks when in a cafe, when we went to London he bought lunch and wouldn't let me see the bill, even when I said I wanted to pay. I've noticed him raising his eyebrow now and again, when we are in conversation about something, he always seems relaxed around me. He notices me driving to work or around town before I even see him, and if I notice him he's waving at me before I've even a chance to wave myself. But when questioned about the 'hints' and conversations he says; he says random things to lighten the mood. But I'm still not convinced, there's something in these comments which I don't understand. My mate has said how everything he has said to date suggest that he likes me, but why not just tell me?? And that it sounds like he's confused of what he wants. i guess I just want to know, what he's thinking, I want to be able to help him overcome his situation regarding his past relationships. Any suggestions, advice greatly appreciated and I thank you in advance

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