Ask him if he could go out with any of your friends, which one would he go out with. It usually will stump him. If he doesn't answer, you can tell he doesn't want to upset you, but if he answers before you can finish the question, you got some problems.
Which part of my body should be improved?
Have you ever had sex, how man guys have you had sex with.
Ask her about the "facts of life."
There are a lot of questions you can ask someone that would seem awkward. Asking someone why they look the way they do can be awkward and asking someone if they will lick the floor is awkward.
Questions about their ex-, asking them if they're pregnant, asking them if they're the one who forgot to flush the toilet.
It depends on where you are, and what situation you are in. For example, if you are on a date and there is an awquard silence, then the best thing to do is to ask him about his day, or something that you can both relate to. Don't ask him something you have no interst in.
You could ask questions about the fake girlfriend to get some info or forget about he's not worth your time or effort if he has to make up a fake girlfriend.
Do you want it hard or soft, fast os slow,are you tight?
Just ask her. If you are both comfortable with each other this question shouldn't be awkward.
hang out with her more! one on one. go to dinner and talk about stuff. if that or talking on the phone is awkward, texting is great way to communicate. you can ask each other stuff and not have to respond right away and its not awkward. but ask her questions about herself and then answer them too. childhood stories are a fun conversation topic