Shy around my crush

[hmdreamer7]

There is a guy that I like, and I really want to flirt with him more, but I'm so shy about it! The thing is, he owns a business near where I work(I work in a store that's accross from his business so we run into each other often), so whenever I see him during the day, we just like to talk about business stuff, or just chit-chat, or have friendly conversations.

 

But at night if I see him at the bar - AND if we've both had a drink or two and are a little tipsy - we're usually cracking jokes w/ each other, giving hugs, and being a little flirty. It's fun, but I think now I've developed a crush on him, and I can't act the same around him anymore!

 

What I want to do is flirt with him more, maybe get to the point where we'd go on a date... but there are some things holding me back. First and most importantly, he really liked my sister last year... and asked her out! But she doesn't like him at all and turned him down. I'm worried that he may still have feelings for my sister, and therefore me flirting with him will be weird for him? I'm totally okay with the fact that he used to like her, but if he STILL likes her, then I don't want to make a fool of myself and keep pursuing him.

 

The second thing is that since we've mostly had a professional-like friendship, that I don't know if I could separate both my personal life and my professional life around him, if I were to push the flirting with him at the bar to doing more than just the harmless hugs and jokes. I guess what I mean is that want to have fun with him, but I still want him to respect me.

 

I don't know, are either of these things a big deal? Should I still go for it, or should I move on?

 

Okay, I have to go to work now, but I'll be back on my lunch break/after work to read, thank you in advance to anyone who has advice for me!

[COtuner]

If you're hugging in a bar, your "professional" relationship is already taking a hit. And after a year, I would doubt he is pining for your sister to the degree he would not go out with someone else. Just ask him out!

[Roberto34]

Yeah, don't wait too long to make your move...go for it, or you'll surely regret not doing so.

 

At least you'll have an answer.

[Xylitol]

I think throwing out your shyness out of the window is the best thing that could happen in your life. So far you being shy has rewarded you with nothing, so my advice would be to go for gold in your life, put your feet off the brake and onto the gas pedal instead.

[hmdreamer7]

Okay, with 3 votes to go for it, I guess I'm gonna go for it!! Thanks all... now I just have to figure out how to do it!!!