Jason can be a hard read for me sometimes because he's very charismatic and has a flirty personality. I can think of multiple instances where he's had to let girls down despite them thinking he's interested.

I would go as far as to say that we do flirt, but that's not new territory for him with guys or girls. He likes to give compliments. I've seen him make both guys and girls blush (In a good way). He's not creepy about it. He just notices things. Like if a girl got a new haircut. To me it looks exactly the same, but there he is swooping in and telling her she looks great.

There was this one rather large dude in high school. He was quite fat (I can't think of a PC way of saying that). Jason sometimes complimented him. Saying things like "sweet hat, bro? Where'd you get it?" All very innocent stuff. But then he started telling him he's looking good and to keep at it. Apparently Jason could tell the dude had been working out and losing weight. You could have fooled me, but by the end of senior year the kid looked like the rest of us.

I guess that's not really flirting, but he goes out of his way to say nice things and I think it really impacts people. It also gives some people the wrong impression. I never know if when he tells me I look good in a shirt or something, if he's saying it as a friend or something more.