Well when my site was #3 in Google.com for "chat rooms" (it fluctuates a bit so it might not be #3 at this moment), this keyword/phrase was sending me about 1,000 of my approximately 3,000 visitors/day. This is more than all my long tailed searches combined. For example, I've been #1 in Google.com for "singles chat rooms" for a long, long time now, but this key phrase only sends me about 30-40 new visitors a day.

Now I do understand what your saying. I do get a higher see more signup rate for long-tailed search phrases. Also, these phrases are a more reliable form of traffic. Nevertheless, I certainly don't mind the traffic I get from "chat rooms". And if any SEO expert could guarantee me a top 5 position in the SERPS for a word like "chat" or "dating", I would gladly re-mortgage my house and pay this expert anything he/she wanted. Sadly, however, I know nobody can make this promise without lying through their teeth.

I guess the big question for me right now is how to acquire more targeted traffic from people who are looking for exactly what I'm offering. My bounce rate is around 33% which is way too high. I realize that "chat rooms' is not the best way to summarize my site. However, ranking #1 for "late night hook up" definitely doesn't send me many visitors.