Why Don't I Do That More Often?

I chopped a good chunk of my hair off yesterday...or rather, someone with a license to cut off hair did. Really short in the back, longer in front, especially longer on my right side to kind of hang over my eyes. The longest piece barely reaches my chin.
It looks cute if I do say so myself (and I do). Granted I haven't had to style it yet so who knows, maybe I'll shave it off in frustration later. Lady said it brought out my cheek bones, but to be honest they don't need to be brought out since they seem to do that fine on there own.
Everyone likes it though, I stopped by work to show a friend, and then went over to Andrew's (you know, that guy I work with) to show him.
I don't have many male friends for the simple reason that they make me uncomfortable and I don't know how to act around them. Anyway, I go over there and I see Andrew and Ryan, two guys that I am slowly becoming comfortable around, though I still don't want to just go hang out (I forced myself to yesterday, turns out I don't like being called a coward, even if it's in my head). They are not the only guys there unfortunately, there was Daniel, a freshman who seems like one smart cookie (I like him, he's not intimidating, but he's smart) and then there were two others. The only reason I was able to make myself stay was because for the most part, all but Ryan and Andrew were easily deemed 'kiddies' in my eyes, and that always makes me feel better.
I stayed to watch them play football (yeah, that killed), and went in to eat pizza. Right away Andrew's mom rushes forward and goes "Are you 'blankety blankblank'?" (ha ha, did you really think I'd tell you my name?). Awkwaaaaaard. I kind of laugh and nodded she shook my hand and starts talking to me, someone else comes up and goes, "So then I take it you and Andrew are dating?" Shocker....I said no, and I'd have been outta there if Andrew had heard.
I could go on all day giving you the skinny, but bottom line is that by the end of 'dinner' I was feeling pretty confident. I mean around my friends (my female friends, let's face it, I can count on one hand the number of male friends I have) I'm confident and everything. I crack jokes, I'm sarcastic, I'm me. This was different though. I still wasn't comfortable enough to do much of that, but with Ash and everyone I call attention to myself by being obnoxious, I get what I want without feeling awkward, and no one calls any attention on me.
With all of them I was kind of trying to stay off the radar and they're all, "No, no that's ______'s seat" and "Hey man, ladies first!" and "You've got cool hair, but man no one can beat ______'s" and possibly the best of all was the "I lie all of the time, for instance, ______ you're ugly. That's a lie, now here's the truth _______ you're beautiful." Que my even more red face and, "Ha ha, thanks." And then Andrew's offended, "I say that all the time and you look at me like I'm a creeper!" "Because you only say it right before you ask her to take you to Taco Bell" (Ryan) "I agree with him." (Me) "That's not true, you guys are making me look bad in front of my mom." (Andrew).

So I left there feeling good about myself, I mean we're friends so I don't expect, "You're ugly." But there's no need for the compliments, and I don't know how to respond with so many. To be honest I've never really found myself that pretty, I mean I never thought I was drop dead ugly, but it's nice to hear. So the question remains; why don't I do that more often?