Some women are naturally aggressive, but that's not always seen in the best light. Others are pretty passive and introverted, which may leave them wanting in life. I'm somewhere in the middle. There are lots of women that won't initiate conversation or a dating scenario because of tradition and not wanting to be perceived as "easy" or "thirsty". If you're like a large majority of woman in the dating pool, the transition from single to dating can be tricky, but there are ways to let a man know you're interested without being super aggressive and/or awkward. If there's a likely candidate in your circle, here are a few things you can try.
1. Try asking what he's doing for lunch/dinner on a specific day.
The key here is adding the specific day. This implies a date if he agrees, but you're not blatantly asking. There's always some new restaurant that you've been wanting to try, but don't want to visit alone, right? If not.. find one. Here's the chance to impress him with your eclectic taste in cuisine, but don't go overboard and try something too weird. This can ruin a first date if something "doesn't agree" with one or both of you. (Also, if things move toward a 'date', be clear on the payment arrangements before getting there. You don't want to kill your hard work by ending the date awkward.)
2. Ask if he thinks the latest blockbuster would be a good movie to watch.
Ultimately, you just want to get him talking about his taste in movies so that you have more "intel" to work with later. Maybe he'll ask you out to that specific movie after he offers his opinion. While a movie date isn't great for the first date, it's a foot in the door, right?
3. Invite him to something personal (like a performance).
This implies that you want him to see a side of you that he hasn't already and that he's special for acquiring this invite. This is also a chance to impress him with some hidden or obvious talent you have. You can also accomplish the same affect if you share something personal that you wrote or created with him.
4. Parlay your compliments into conversation.
Don't just tell him he smells good. Ask him what cologne he's wearing and piggyback off that conversation starter. Do this with anything. Compliment with a question to initiate a longer conversation.
5. Ask him what the dating scene is like in his city/area.
You basically just want to know how he feels about dating and if he's dating someone currently. This asks those questions with no pressure. It shouldn't make it awkward for either one of you if he's actually dating someone. (Oh... and if he says he's dating someone, back off completely.)
Remember, it's the combination of a few of these that will drive the message home. Using one tactic may still be overlooked by a man that needs a little help seeing you in that way. Once you've tried a few with no response... at least you tried... AND... you won't have egg on your face. Hopefully, these tips will work to get you to start dating your prince.