My museum dates were taking advantage of free museum Tuesdays for residents.

You have stated you live in Boston, I was there last year. Beautiful city with so many inexpensive museum options, plus the massive park that had events going on every day that I was there and the historical walks were great. Try some of these:

• Harvard Museum of Natural History: $15 per person, $75 individual membership
• Isabella Stewart Gardner Museum: $22 per person, $75 individual membership
• The Institute of Contemporary Art: $20 per person, $65 individual membership
• Museum of African American History: $15 per person, $35 for basic individual membership with one guest, $75 for the same with 2 guests
• The Sports Museum: $18.47 per person
• USS Constitution Museum: $15 per person
• Harvard Art Museum: free
• Boston Public Library: free. This one was my absolute favorite, we spent 4 hours wandering the halls looking at paintings and sculptures, I could have been there all day

Many of these have discounted admission for residents and members. There is also the Boston Aquarium, which is $39.95 per person, but that can easily be turned into a multiple hour event and membership is only $79 per individual. They aren’t all $50, you just have to look at their websites and check for discounts.