[El Bastardo]

The following is a confidential post. If the member would like to reply to any comments please PM me


Here's the deal: I'm 20 and I've never in a relationship. I've always felt unconfident about myself because I'm a little chubby (you can't tell if I'm not shirtless, usually) and I didn't know how. So I've never asked a girl out and never had the intentions to because I thought I'd always get rejected. Since then, I've been getting into shape, being more confident in general, and feeling good about myself for the first time in a long time.

Right now, one of my best friends' (girl) friend (girl) is someone that I want to ask out. I've met her a few times and we've all hung out, but we're not really close. So she's, in my opinion, at that perfect distance of friends but not too close so it wouldn't be that big of a loss if we don't end up together and it would be very awks. She's real nice, kind, sweet and pretty, completely innocent in her mindset (can't read sexual innuendos for the life of her), and single (YES).

A few problems:
1. My best friend is someone who has told me we should go out twice, I kissed her (a lot) at a club once and was grinding like mad with her, and we also had sex (got whiskey dick). It's been 2 years since the day she last told me to try to date, but I said no (no confidence, even at that point because I didn't want her to see my naked body). Would it be weird if I asked the girl out even with this history? They're best friends, but they're pretty close too.

2. First time asking anyone out, so I've got no game. I sort of have an idea on what to say and what date to do, but I don't know how I would ask her. Should I call her up, wait until we all hang out (it wouldn't be too long because my friends are friends with her too), or some other way? I really don't want to overthink this, but I want to do this right.

3. Oh, and she's white and I'm Asian. That's gonna set me back right?