If you are friends with one of the targets friends, is it safe to tell the friend your interested and ask her friend if the target has a boyfriend? Or should you just go for the approach?

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Just DO It!

If one of your friends is also your targets friend then this is perfect...

You can find out anything about the target that you want to. If your friend
says that she can't tell you that, just lay a guilt trip on her like...

"After I have defended your honor from people saying shit about you, this
is how you are going to treat me... I can't talk to you right now..."

She will want to know who said what, blah blah... just tell her...

"Here's how this is going to work... you answer my questions about the
target, and I will answer all of your questions about who said what..."

Now, even though no one has talked shit about your friend, you have to
make some shit up. Don't give her real names, just tell her that you were
talking to some of your friends, and one of your friends had someone else
approach them and start talking about her... out of no where, saying that
she is THIS and she is THAT...

Then, tell her how you defended her honor and was about to lay this chump
out... but he was pulled away by either his sister or some girl that was
pissed at him and was wanting to talk to him...

This should work to get the information out of her in the event that she
does not just tell you straight up what you want to know about your target.

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That is fine, but you got to feel the vibe. Most likely she already figured that out...