I'm very fond of "First Night" by Jack Neary.  Witty and wistful, with a smile-on-your-face ending.  Check the link.

http://www.jacknearyonline.com/firstnight.html

Or, if you can stretch to a few more actors, "Somewhere In Between" by Craig Pospisil is as funny and heartwarming as you can get.

I highly recommend both.

This is one that I'll be following as well.  I would love to do a Valentine's weekend show of this sort ... and a two person show would be perfect!

I agree with donzolidis (does that rhyme with tonsilitis?) that "Almost, Maine" is a charming show.  You do need at least six actors to make it work.  It concerns a dozen couples all having a conversation about love.  Mostly funny and quirky and touching, a couple on the sad side.  It's presented in twelve separate scenes, but all the scenes are actually all happening at exactly the same point in time on one evening in Almost, Maine.  (A town that never legally incorporated themselves into a town, so they became "Almost, Maine.")

"Star Spangled Girl" is the best Neil Simon show that no one has heard of.  It should be done more.

On the two-character end of things, there's also "Talley's Folly."

Eight characters will give you "Enchanted April."

Originally posted by dri1962 For a 2-3 person play, how many actors do you need assuming that some may bail or not be available for all performances?

Two years ago, a short play I wrote was selected for a competition. I decided to direct it myself, and needed 3 actresses. Over the summer, and up to two weeks before the performance, I had 15 young ladies accept a part, then drop out after a week or two or rehearsals, leading to a hasty recast. I finally had to drop out of the competition. So in my experience, you need more than 15 (grins). Your results may be happier.

Originally posted by dri1962 Question....   For a 2-3 person play, how many actors do you need assuming that some may bail or not be available for all performances?   Thanks....

2 or 3 ... If I knew ahead of time that someone wouldn't be available for all shows then they would not be cast.  I've not yet had anyone bail and really in a very small community such as ours ... that actor would probably have a hard time getting on stage again.  Many of us are involved in multiple theatre groups and word travels FAST!