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I don't think it's as much as a self-esteem issue as just not being receptive to the joke, or just not getting it. Try something more universally funny than a movie reference.
I start off with "Hey, you look fun/sweet. Of course, I could be completely wrong, and those looks/that smile is hiding a ferocious chihuaha, who knows... ;P"
Obviously, I use just one variation that fits. This line is the least flexible part of my first message, and yet I variate it sometimes.
Then I comment something on the profile that gets a reply, or ask some questions her profile didn't answer, combined with some C&F. It all depends on the profile, I never send the same thing twice, but the chihuaha thing fits nearly everywhere. My profile is written in a similar tone.
After that it's straight game. I usually get an IM address by the second or third message.
It's spelled "chihuahua". Yeah, I just changed your life.