Mike, this is a trick question, right? Depending on your crankset, you can certainly get a smaller chainring. Without knowing the BCD, I can't tell you how small though. But no one here can answer the out of shape part, besides you.
How do your legs/lungs feel on climbs? Do you have a heart rate monitor? Do you want to throw hill-climbing into your weekly rides to build on that, or are you content to sit at the back while everyone waits for you? Personally, I hate hills. Because of that, I never trained for them. So when I was in my best shape ever, I could kill it on the flats but would get dropped on long or steep grades.