In my opinion, the best way to do this is to incorporate one or
both of the following: humor and context. That is, be funny, and try not to be
totally random. Humor is in the ear of the beholder, but context is pretty easy
to explain. For example, if you’re shopping at a supermarket, and you see an
attractive guy picking up a bag of Party Meatballs, you could casually stroll
up to him and say something relating to how often you party hard with those
meatballs and your friends.
The point is that whatever you say, it helps if it's relevant to
the situation you both find yourselves in. Men will appreciate that you pay
enough attention to draw some parallel between the two of you, as opposed to a
completely random statement that could essentially be directed at guy in the
world. By providing context, you’re creating a shared moment, and that is much
more likely to engage him. So whether it’s about the song playing on the
jukebox or his really awesome band T-shirt or his choice in toppings at the
self-serve yoghurt place; commenting on your shared surroundings in a humorous
way is the best way to go about it.
What's also a pretty
solid no-fail tactic is if you ask him a question with an "either/or"
option, a question he'll be forced to give an answer to, and then — no matter
what his answer — disagree with him. Never ask "yes" or
"no" questions; you're just giving him an excuse to bow out. But
something like, "My friends and I were just discussing something. What do
you think: Harry Potter or Lord of The Rings?" And
no matter what he says, shake your head and look puzzled, like he has given the
wrong answer. It'll spark discussion and annoy him just enough to keep him in
the conversation.
It might not always
work, but it’s for sure the least creepy approach. (For the record,
commenting on how hot he is — that's usually creepy and not awesome. Don’t do
it.)
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