Wow... big question here. While I'm tempted to use the old, "age is just a number" adage... there are probably some things that should be considered first:
-Would the understanding be that this would be casual?
-If no, do you think you'd have enough things in common to continuously entertain a younger lass (or conversely she to entertain you) without sex?
-If something went horribly awry in your tryst, would you be able to maintain a civil/decent work relationship? (just to play devil's advocate)
With that said, I'm usually a go with your gut kind of person. 3 months is a long time to go without any physical intimacy (although I've known folks who've gone much much longer without, see: Supra)
. Perhaps, if anything, maybe just taking a couple casual dates with your friends of friends would be a better start. Get your feet wet without jumping into anything that may have bigger consequences/implications. As I totally understand the "picky" nature you describe, you don't have to be head-over-heels with someone to get a cup of coffee or grab a beer.
If you honestly think you can get your knob polished and it NOT royally screwing anything up at work... why not? With what you're going through, I can't help but feel, you owe yourself a little fun.
At the very least - I can always send Jako out for a sensual massage with a super happy ending.
