1.The person approached will probably question the situation. Whether or not is it a prank or some true or dare being played by a group of people and you are the pawn of the game.
Verdict: Very likely the approacher will be rejected.2.The approached will question again. "What intention does the the approacher bear to do this?"
Verdict: Most of the time the approacher will still be rejected.
3. The approached base his/her decision on the basis on how he/she was approached and the first impression the approacher had on the approached.
Verdict: Most of the time, approacher will still be rejected.
This leads to the question: Should you make the first move?
Seems like the answer is a straight No. For hardcore people who believe in You Never Try You'll Never know, go ahead and make a hit (for you may just strike a jackpot).
So, How How How??
Seriously, I have no idea how. I never tried doing this and I never accepted anyone who approached, but I have some advices.
Focus: Try to make the hit at natural as possible but yet creating an impact on the other party.
Don't rush into matters and try to get personal particulars (eg. phone numbers) on first attempt. First impression counts alot!! (To many, this is easier said than done. It takes some wittyness to get the going, going)
Don't try to let the approached to take pity on you and make a forced acceptance. In explanation, don't say something like, "I have been noticing you for a long time and followed you over the overhead bridge to catch you". You just make yourself sound like a pervertic stalker.
If you are rejected, don't keep quiet and walk away just like that. Say something like "Nice to meet you and have a nice day." Put a fullstop to every sentence as there might be chance to start another sentence. Everything is possible.
All the best!