Want to ask out shy/awkward girl, not sure if she's interested or not

So there's this girl that I go to school with. She's really cute, funny, extremely intelligent, lots of great qualities. About two years ago, her friend told me that she was interested in me. I tried to ask her out, but she told me "maybe after finals." I kind of let it go, even though I did want to get to know her better, and ended up dating another girl for a year and a half. Well, we broke up, and afterwards I did send her some drunk messages about being interested in her and wanting to take her out, to which she responded that I just broke up and maybe later -- which I apologized for and she said that it was no big deal. Fast forward a month and a half, and I'm over my ex and would like to ask her out. The only time I ever see this girl is when she's with our friends (we have a lot of mutual friends). We always end up talking though and she smiles at me, etc. I'd like to take her out and get to know her better, but I don't want to push it if she's not interested. Really don't want to make it awkward for her when we hang out with our mutual friends. I'm not scared of rejection (used to it lol), so I guess I'm wondering how to go about this. I could call her, but then it might be more likely to make things awkward than if I just asked her nonchalantly in a gchat msg or something. Thing is, I don't think she's ever had a boyfriend, so I think she wants me to really chase her (which I am hesitant to do for the above reasons). What do you think?

I should also state that I've gotten a lot of positive signs from her, but it's almost like she's purposely keeping me at a distance even though she likes me. Like maybe she's self conscious or has some demons or something. Thing is, I like her and when I like someone I am very accepting.

Simply ask her whether she'd like to go on a date. Period... And also...

 

She's really cute, funny, extremely intelligent, lots of great qualities.

...stop exaggerating...and...

 

Really don't want to make it awkward for her when we hang out with our mutual friends.

...would it be awkward for you? If not, go for it. It's not you who'd make it awkward for her, it's her that'd make it awkward for herself.

 

I could call her, but then it might be more likely to make things awkward than if I just asked her nonchalantly in a gchat msg or something.

One way or another, doesn't really matter...

 

Thing is, I don't think she's ever had a boyfriend, so I think she wants me to really chase her (which I am hesitant to do for the above reasons). What do you think?

And think less, it's not helping you to see things clearly. And one last thing...

 

Thing is, I like her and when I like someone I am very accepting.

Don't subdue yourself for others.

I don't think she's very interested, or she is very unsure, based on what you wrote. Maybe she thinks you have committment issues after knowing about your break-up. Women usually don't say things like "maybe later" and it sounds like she didn't want to be upfront with you and say "no, thanks". It sounds like the, "maybe later" is more like "maybe never". Hey, I could be wrong though, but when someone likes you or if they are interested they generally don't say things like this.

 

If you want to know for sure then just ask her out. If she says no then leave it at that and move on. You never know what someone is thinking until you ask. If she keeps putting you off and saying stuff like, "i don't know just yet", or "maybe later" it's probably best for you to move on. Good luck

 

Until we meet again...

Her reaction could be because she's not interested, but it may also be like you said, she's self conscious/has some inner demons. I become like that sometimes, i know myself well enough to know that with certain people, as much as i like them, i couldn't be with. I am very awkward and wouldn't want to put them through that. Thing is, the more you push the further she might run. Try talking to the friend who told you in the first place that she was interested. If they are good friends and you 'let slip' that you like her and was wondering if she's still interested, her friend may just be able to tell you.

When I read your post, I felt like I was you and the girl you were talking about was a girl I'm currently pursuing. Cheers and good luck to both of us!