Dates are hard to schedule with small children who require babysitting, especially with a crazy grad school schedule to work around. But we've really been trying to go out at least once a month.
One of our neighbors also has small children and offered a babysitting exchange. Once a month I watch her kids while they go out and also once a month she watches ours while we go out. It's been nice since babysitters can be expensive. The babysitting co-op idea is a great way to make friends and have an evening out. I've even exchanged sitting with another neighbor during the day for appointments and such. We also have some really nice neighbors who have offered to watch the boys, usually about once a year.
Most sitters we've used have charged $10/hr for the two kids. A typical movie requiring 3 hours of sitting would cost $50 ($20 for two tickets plus $30 for a babysitter). Add any popcorn or drinks and it's just too much! That's really the reason we haven't had a regular date night the last few years.
Another option we have used is Grandma. The grandparents all like spending time with the boys, so we can often send them for a weekend with Grandma and Grandpa. We've done that for the last several years. But Grandma Deb is now retired and available for the occasional weeknight evening. Considering many of the Auditorium shows we want to see are during the week, this has been very helpful. We try not to abuse the privilege.
So where do we go on date night? We have gone to movies when they were $5, but the weeknight price has recently gone up, so we will probably do that less frequently. We also like to go to the shows at the IU Auditorium, through the Department of Theater and Drama, or one of the theater companies* in town. And now the IU Cinema is opening, where most movies will be free. We can see lots of classics and foreign films.
*Local theater companies include Bloomington Playwrights Project, Monroe County Civic Theater, Cardinal Stage Company, Theater of the People and Starrynight Productions.