Here’s solid advice, as swiped from /r/okcupid:
The first message:
Probably way out of my league, but I thought I’d still try…
The response received:
You would have been far better off sending me a different message. This shows a lack of confidence…
So, buddy strikes out by showing a lack of confidence. Women love a confident man. Worst case, fake it. And he seemed like her type, too!