Should I even bother?!

Well I decided to give it a try and our first date was great. We really hit it off. Identical sense of humor and a very genuine feeling that we "get" eachother. Set to see eachother again this weekend and we are both dropping hints that we both want to be ::ahem:: "physical" but I feel I should either pace by going slow or go into it knowing I cant expect anything with him being so newly separated from a 9 year relationship (5 yr marriage). And Im nervous to see him! Im never nervous! Im actually thinking things like "what should I wear?" "what should I talk about" "maybe a quick shot of whiskey before I knock on his door!" For sure sign Im into him...

Stop thinking so much, just have fun, be yourself.

This is one of those very tricky situations that requires a lot of emotional intelligence to handle well. Now, the greatest likelihood is that five months is not long enough to have processed all of his possible emotions, and that you will be damaged if you try to get too close. It's also most likely that, unless you are not the first woman he's been out with, you are a rebound relationship for him, and that's never good. The fact is, early dating during the process of ending a relationship where there's a lot of emotion and attachment is most likely going to go sour rather quickly, since humans don't let go quite that quickly, and even therapy doesn't guarantee the speed with which we'll process loss.

However, if the man is mature and is not just testing the waters (but he probably is) then it could lead somewhere. It depends on what you're looking for. For me personally, I think there's usually a lot of denial in the first year after a break-up. No matter how hard you try, you really are still dealing with your feelings about someone else, and it's not fair to the new person (i.e., you) to have to go out with a ghost in attendance.

Worse(r) than this, of course, is when the ex is very much still a part of the man's life. I don't know how likely it is for a new relationship to succeed if the past isn't left in the past. Cues to this include having to listen to details about the break-up beyond what feels appropriate; hearing even well-meaning jibes aimed at the ex, because discussion of the ex is discussion of the ex, plain and simple; and residual anger, resentment, or any other negative emotion (crying, for example) that seems inappropriate. Then you know the other person is not ready.

I had to warn men after my separation (which lasted two years and then we got back together again, for bad reasons which inevitably didn't last) that I was in a precarious place. I don't see the need to rush this process. It takes the time it takes, and you're mourning a major loss to your identity, as well as having to recreate yourself in a new image. This is a huge process for most people. Best-case scenario to fully let go of the past is probably 2-1/2 to five years (not before the person can date, certainly, but before they're ready to really settle down with a new person).

I was married for 25+ years, and so the next major relationship is only in the process of developing. I was not ready for a long time, probably four years beyond when I thought I'd be ready, for something new. It's completely normal to want some time before you make the next big decision, so if the person who is separated or divorced is big on finding someone new right after the marriage or important relationship is over, I'd be very wary indeed, because that's not a good sign.

Good luck!