Playing Cupid

With Valentine's Day just around the corner, I have been inspired to play cupid. The dilemma is how to handle this delicate situation. The girl is one of my oldest friends, been like sisters since we were 5 years old. She is seriously beautiful inside and out. She comes off as very strong and independent, but deep down I know she is just afraid of getting hurt. She has been single for over 5 years now and although she is totally ready to be with someone, has had horrible luck and has really given up on finding love. The guy is a friend of the hubs. They don't see each other often or talk that often but when they do see each other they always enjoy hanging out. He is a bad boy turned cop, who like her comes off very strong borderline cold. In reality he is super shy and just hasn't been lucky in love. With the help of his sister-in-law, we are trying to coordinate this potential love match. The options are....A) Tell them both about the set up and plan a triple date. This is so not a good idea in my opinion because one or both of them are likely to say no and/or triple date with a blind date mixed in can be very awkward! B) Do not tell either one of them, have a small get together at my house, invite them both and hope they hit it off. I think this is the best option, even though one or both of them could potentially flake and not show up at the last minute. I'm not usually the meddling friend, but I can so see these two hitting it off. Even more so, when the guy's own brother thinks it's a great idea. Does anyone have any advice for how to approach this? Have you ever tried playing cupid?