Should I ask out a woman who is friends with a female coworker?

Question

I sometimes join my coworkers for drinks after work. There is a single woman who hangs out with us. She doesn't work with us and think it would be great to ask her out on a date.

What do you think? I'd be very embarassed 'cause we are both very shy.

Answer 1

"Shy" sucks, especially for a man. Do things that you're inclined to do unless there's a valid reason not to.

Answer 2

Go ahead and ask her,the worst thing she can do is say no.

Answer 3

Go for it.