Hi there.

Sounds like an awesome plan. I'm a 30-something, but I would recommend maybe taking in a show at the Improv Asylum (there's a location right in the North End - a great area to explore and get amazing food). My friends took me there for my bachellorette party a couple of years ago and we laughed and laughed.

Dancing... well, if you want to avoid the throngs of 20 year olds, my advice (and maybe others will disagree, but...) is to avoid the area right near Boston Common known as "The Alley." Meeeeat market for 20somethings. (I used to love it! lol)

Not to break the bank, but as a special something, perhaps just go up to Top of the Hub - the restaurant/bar on top of the Prudential Center. They say that if you go for a drink between 7-9, the views of the city and sunset are breathtaking.

Just a couple thoughts to get the ball rolling... have a blast!

To kick off the weekend you may want to see Menopause the Musical. Lots of laughs for women of our age range. For dinner, especially if it is early September strolling through the North End is fun. We just dined at La Summa and everyone loved their meal. Not a pretentious place at all. You may also be lucky and find some freebies. Here's some things happening at the Hatch Shell: September

Fri. September 1 - WBZ Free Friday Flicks SUNSET

Sat. September 9 - The River 92.5 Concert TBA

Sun. September 10 - Boston Comedy Festival TBA

Sat. September 23 - The Boston Blues Festival NOON

Sun. September 24 - The Boston Blues Festival NOON

Although I don't have first hand experience on this one-- for drinks I frequently see the Foundation Lounge and the Oak Bar mentioned. Finales for special desserts recommended too. ENJOY!

Thanks for the help the Improv Asylum sounds fun, any dance places for over 40... Can't wait