I think that i'd advize making it plainly obvious with both flirting  & telling - but make sure not to ask him out! Provoke the guy to be a man in more than anatomy, what woman wants a guy who is such a coward he won't even ask a girl out.

Ruth I think is a good example (though perhaps not one to follow in full as it would be risky to sneak into his bed - may end up in sexual sin or if him chucking you out & calling you a slut) - Boaz obviously liked Ruth but was making no effort to win her so she put herself in his way provoking him to action.

Ask for lifts to places you know you are both going, make effort in dressing attractive (keep it modest though). Again in the Bible the lady in Song of Solomon isn't afraid to ask where Solomon would be at lunch time so they could have a rendevouz (1:7) but makes it plain she isn't going to play the whore to get his affections as she says she wouldn't be like the prostitutes who veiled themselves & followed workers around hoping for a quick £.
But she does ask if he wants to meet up though I don't think its a proper full on date!  - Rather it's Solomon who comes to her house in 2:8-10 to ask her on a date.


further advice would be
~Make sure it's you as a whole & not your simply body that is winning his affections.
~Make sure he loves Jesus & ask about his daily devotions & experiences with Christ.

~The qualifications of an elder that Paul writes in 1Timothy3 are the high calling of every christian guy (whether or not there are or ever will be an Elder) look for evidence of these & his striving after these in his life.

I could probably write more on this whole thing - check out http://worship247.org/news-item.html?&tx_ttnews[tt_news]=6&tx_ttnews[backPid]=7&cHash=5c2ffa4541 for a series I taught on Song of Solomon's teachings on attraction, romance, sex etc...
(Though i'd add a fair bit to it now if I were to teach it again it's a core of what i'd teach anyone on this subject from a biblical perspective.

May Christ direct your steps & lead you into a liberated relationship with a godly guy that results in a full on marriage for the glory of God & your joy