Help needed!

My hubs is not very good at planning dates, ranging back from when we were still dating, so for Valentine's Day, I am creating a "Date in a Box" gift for him. I am going to pre-plan (and pre-pay) for 4-5 dates, put all of the info into individual envelopes, and give him the present.
Ideally, the envelope will say something like "Evening date, dinner included" and then I'll have a gift card to a local dinner and money for bowling, or something similar, but I'm not sure about my ideas. I was planning dinner with bowling, a night at the drive-in, maybe a visit to a park and gelato/frozen yogurt, but I don't know what else. I'm hoping for about 5 dates, each worth no more than 30-40 bucks.
Any suggestions?