Most Helpful Guy
It really depends on the guy.
A lot of guys lack confidence, and even if they really like a girl, they lack the courage to approach a girl and the experience to do a good job at it, so often, nothing comes of that mutual attraction.
A guy who is more of an "alpha male" may absolutely enjoy the chase, and wouldn't be as interested in girls trying to take the lead.
You really have to know a bit about the guy in question.
Most Helpful Girl
All of the guys I've talked to hate the chase. If you play hard to get, it'll backfire 99% of the time. Don't do it.
The only ones who would lose interest for "being easy" are players who aren't interested in you to begin with.
There's nothing wrong with contacting first, I always contact first and I have had a very easy time getting a boyfriend.