It doesn't have to always be on the same night, but it's helpful to pencil in one night Not all dates have to involve going out, but if you have young children. There are a ton of fun, cheap date ideas! 98 Cheap Date Ideas Go on a very long walk around your neighborhood at night. 9. Go to a real- live movie store. Author Chrissy Stockton shares with us 50 cheap date ideas. Bowling is always a fun night out, and if you go during the week you can find somewhere to do it. Head to the Farm and go Berry Picking Berry picking is a fun dates to go on at night, and also one that allows for a lot of talking and getting to know each other time. Anniversary Date Ideas When you're planning an anniversary date, think of doing something special and celebratory—and reflecting on your relationship a bit. Find a Rooftop Pool and Go Swimming Rooftop pools are popping up everywhere from hotels to sports clubs these days. Taste wine at a vineyard or winery. Don't tell your partner you have something planned, and create a fun night.